About Kissimmee - Located right in the center of Florida, in Osceola County, Kissimmee is a family-oriented destination known for its off-the-beaten-path adventures, endless sunshine, and proximity to world famous theme parks. It checks all the vacation-planning boxes with both natural and man-made treasures. Commonly referred to as “Kissimmee-St. Cloud” area due to the short distance between it... read more
About Kissimmee - Located right in the center of Florida, in Osceola County, Kissimmee is a family-oriented destination known for its off-the-beaten-path adventures, endless sunshine, and proximity to world famous theme parks. It checks all the vacation-planning boxes with both natural and man-made treasures. Commonly referred to as “Kissimmee-St. Cloud” area due to the short distance between it and the adjacent city of St. Cloud, Kissimmee is that Florida destination with a wealth of attractions, dozens of great outdoor areas, and hours of sunshine almost every day of the year making it the perfect choice for short vacations and long-term stays. For your accommodations, Owner Direct can provide vacation rentals that will help you get the most out of your Kissimmee trip in a hassle-free way.

Where to Stay & Why - Owner Direct offers a wide variety of vacation rentals in Kissimmee, even pet-friendly homes with spaces where your furry pals can run around. No matter which lodging you choose, it will surely have multiple rooms, furnished living areas, a fully equipped kitchen, private pools, patio with a BBQ grill, and parking space(s). Some homes even have a hot tub, games room, theater room with surround sound, a breakfast area, and a screened lanai.

Other amenities can include TV (some have them in every bedroom), cable, high-speed internet, free phone calls within the US and some countries, DVD player, AC units, fans, washer and dryer, and for those traveling with babies or toddlers, there are even homes that provide high chair, crib, and an extra Pack ‘n Play.

If you decide to stay in a condo rental or a villa in a gated community, you’ll have access to the community park, BBQ area, clubhouse, and common pool.

What to See & Do - If you’re here for theme parks, go to Disney World - “The Happiest Place on Earth”, or step onto the movie set in Orlando Universal Resort. For adrenaline-rush attractions, head to the Forever Florida Ziplines, Panther Pounce tower jump, or the Peregrine Plunge. You can speed across the water on an air-boat at Cypress Lake or go canoeing at Shingle Creek Regional Park. Love shopping? The city boasts several malls and outlets, like Perfume Paris and Nike Factory Store.

Kissimmee is also a haven for nature lovers, and home to varied bird species and wildlife. Kissimmee lakes are popular with anglers. Take a trip to Tohopekaliga Lake and explore the Floridian flora and fauna, or stay on land to check out other entertainment spots. Florida is famous for alligators, and you can admire the great reptiles at Gatorland. Observe thousands of different species by riding the Gatorland Express Railroad or Screamin’ Gator Zipline. You’ll find recreational parks with playgrounds, waterside piers, boat slips, and social spaces in Downtown Kissimmee. Old Town is both an amusement park and a shopping mall. It’s a retro recreation of decades past, giving visitors a nostalgic trip. For something educational, take the young ones and young-at-heart to the Museum of Military History and Green Meadows Petting Farm.

Where to Eat & Drink - Foodies love Kissimmee. Everything from steaks and BBQ, to Mexican and Chinese food, can be found close to the city center. For a special night out, try Medieval Times on Irlo Bronson Highway, where your meal is accompanied by medieval entertainment like jousting, in an actual castle. The Bahama Breeze Island Grille offers a taste of the Caribbean, while Cafe d’Antonio serves tasty Italian dishes in a beautiful lakeside setting. Dessert? Kids will be amazed seeing ice cream made with liquid nitrogen at Abracadabra Ice Cream Factory on Main Street.

How to Get Here & Getting Around - With three airports serving the Central Florida area, getting here is easy. You can get in via the Orlando International Airport (MCO), Kissimmee Gateway Airport (ISM), or Orlando-Sanford International Airport (SFB). If you’re driving, take exit 242 if you’re coming from the north, or exit 249 from the south. Those traveling from Daytona Beach or the Tampa Bay area can take the I-4.

Getting around Kissimmee using public transportation is easy, but having a car is an excellent option. If you intend on visiting several theme parks, plan day trips and outings to the coast or Cape Canaveral, you will be able to control your schedule.

When to Go - The fantastic Florida climate makes Kissimmee a great option at any time of year. The three high seasons are Spring Break (March to April), Summer, (June to August), and Winter (December to January). The city tends to be busier at these times and attractions like Disney World are packed. October is one of the best months for a vacation here. It’s still warm, the city is less crowded, and there are Halloween events at Universal Studios for adults and Disney World for children.

Looking for more inspiration on what to do during your Kissimmee vacation? View our travel guide for ideas to add to your trip!

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  • Gated Emerald Island

    Kissimmee: Emerald Island: Townhouse in a complex
    3 BDR • 3 BA • Sleeps 6 • #49171
    110 to 210 USD/night
    Gated community, overlooks pool and only 3 miles to Disney world. Free WiFi This 2-story townhome is the "prime" location in Emerald Island - simply walk out the sliding patio door to the pool and jacuzzi only a few feet away.
  • Luxury 6br Windsor Hills

    Kissimmee: Windsor Hills: House
    6 BDR • 4 BA • Sleeps 14 • #234418
    379 to 799 USD/night
    Welcome to this 6 Bedrooms Home At Windsor Hills Resort With Private Pool, Game Room LUXURY & COMFORT You will definitely love this house. We have furnished the home to the highest standard and chose only high-quality furniture and appliances - Because we understand how important it is for you to have all the comforts of home after a long day at Disney. BEST LOCATION and AMENITIES Only a few minutes away from Disney, the most popular "Windsor Hills Resort" is simply the BEST combination of location and facilities. A huge Resort-Style Pool, Water Slides, Hot tub, Game Room, Tennis Court, Spa, Fitness Center, Theater Room, Basketball Court, etc. All of this is INCLUDED when you stay with us and is only a few minutes’ walk. And lots of extra services, such as discounted Disney tickets, shuttle to park, available at resort welcome center. WE PROVIDE EVERYTHING YOU NEED ! - East Facing Heated Pool and SPA in screened lanai, Our villa is one of the largest highland corner lots, far from neighborhood - 6 luxurious bedrooms with 3 KING/1 QUEEN/2 FULL/2 TWIN - Gated community with 24 hour security guard - Games Room with pool table and Foosball - Large HD TV in every room - FREE high speed WiFi internet - FREE full size crib, high chair - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Laundry Room with full size washer and dryer, iron table - For Senior Guests: Bedroom on first floor with super comfortable mattress - Easy check in with secure key-less entry - Pool heating is an optional fee 5 STAR SERVICES. Our vacation home is professionally managed by the top Property Management Company in Windsor Hills Resort. We spend more money to get you the BEST service. Because you are our guests, we care about your vacation and we want you to be 100% satisfied with our vacation home. SAFETY & SATISFACTION GUARANTEED ! As full-time vacation home owners, we have been in this business for many years with hundreds of happy guests and 100% positive reviews. We know what you need and we care about what you think. Book from us, your satisfaction is guaranteed!
  • 4br/3ba, Renovated

    Kissimmee: Cumbrian Lakes: Villa in a gated community
    4 BDR • 4 BA • Sleeps 8 • #207113
    119 to 160 USD/night
    Located in the quiet gated community of Cumbrian Lakes. Exclusive 4 bedrooms and 3 full bathrooms, including en-suite in the master bedroom. Can accommodate groups sleeping 8 guests. The master bedroom features a luxurious King size bed with private bath and shower, his and hers walk in closet. The second bedroom has also a beautiful King bed that has its own full bathroom. The third bedroom has an elegant Queen bed that shares a Jack and Jill washroom with the fourth bedroom that has two twin beds decorated with Mickey. You have a formal dining room and sitting area with kitchen and living area open space concept, leading to the patio pool area and your covered lanai. There are flat screen TV`s in all the bedrooms and family room. In your home there is lots of amenities offered. The full size kitchen offers modern appliances, dishwasher, microwave coffee maker, etc ... There is a full washer and dryer. You have cable TV, DVD, blueray, stereo music system, ps2 playstation, multiple choice of movies and board games. That`s not all... Professional pool table, air hockey and foosball in the game room. Free high speed internet and long distance calls to the USA, Canada and Mexico as well. This 4 bedroom Florida vacation home is located just a few miles from Walt Disney World Resort, Universal Studio, Worlds of Discovery Sea World, Aquatica and Discovery Cove. A 45 minutes drive to Daytona Beach. I also have a 7bd/7ba home listed on Owner direct with listing #210103.
  • 8br Windsor at Westside

    Kissimmee: Windsor At Westside: House in a gated community
    8 BDR • 1 Loft • 6 BA • Sleeps 21 • #248926
    478 to 849 USD/night
    Absolutely perfect for multi-family groups, or golf groups, this property features all the comforts of home and more. Book your vacation now at this beautiful home with pool and spa located in the gorgeous Windsor at Westside Gate Resort. Plus as our guest you get to enjoy all the amenities of the resort such as the lazy river, splash pool for the kids, 2 other large pools, tennis courts, fully equipped exercise room, on site cinema, arcade games, and family restaurant The space 8BR/6BA home in Windsor At WestSide! - 8 Luxurious Bedrooms (2 King, 1 Queen, 1 Queen/Queen, 2 Twin/Full Room, 1 Twin/Full Bunk Bed) , 1 Crib, sleep for 21 people - 6 Full Bathrooms - 3 Bedrooms With Private En-Suite Bath - Loft with Big Screen TV, game console, Pool Table, and Foosball table - Gourmet Kitchen - Spacious Sitting and Dining Area - Private Pool and Spa, Child safety fence installed - Complementary high speed WiFi internet access in unit - Digital Cable TV included - Baby gear included (crib, high chair) - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Full sized washer and dryer included in unit - Hair dryer, ironing board & iron included - LCD TV with DVD player and Nintendo gaming console - Friendly customer support from a dedicated manager throughout your stay - Gated community with 24 hour security guard Guest access Plus as our guest you get to enjoy all the amenities of the resort such as splash pool for the kids, 2 other large pools, tennis courts, fully equipped exercise room, on site cinema, arcade games, and family restaurant. Other things to note POOL HEATER: Optional Pool/Spa Heat Fee: $35 per day (tax included) Please note the pool heater works thru HEAT EXCHANGE and might not function with weather near freezing temperatures. The pool heater must be turned on for the full duration of your stay. BBQ Grill We rent grill from equipment rental company. It's delivered to home with full propane. Three burners Grill is $85/week (tax included) and $15 for each additional day. Four burners Grill is $105/week (tax included) and $15 for each additional day. Please let us know which type of grill you would like to reserve
  • Family 5br Pool Villa W/

    Kissimmee: Creekside: Villa
    5 BDR • 3 BA • Sleeps 10 • #204481
    159 to 279 USD/night
    This Beautiful and Spacious Family is the Perfect Place for your next Family Vacation. Enjoy your privacy with a completely fenced in back area and lush tropical landscape. As you enter this lovely home, you will be impressed with the the spacious hallway and living room. The living room is a great place to relax in comfort after a busy day at the many attractions. Step out and relax on your screened pool deck or take a swim. with a completely fenced in back yard you can enjoy your privacy. The home is equipped with playpen, stroller, highchair and safety gate for stairs! CREEKSIDE is located close to all major attractions, dining and shopping.
  • Fully Furnished 3 Bedroom

    Kissimmee: Emerald Island: Townhouse in a gated community
    3 BDR • 3 BA • Sleeps 6 • #241471
    89 to 99 USD/night
    This spacious townhome with 3 bedrooms, 2.5 bathrooms is located in Kissimmee in a safe and secured Gated Resort Community, off Route 192. The house is minutes away (2 miles) from Disney's Hollywood Studios, Magic Kingdom, Animal Kingdom and Epcot. It is 20 minutes from Sea World and Universal Studios. Super Target, Wal-Mart and Orlando Premium Outlets are within 10 minutes. Several golf, fishing and boating facilities are also nearby. When at home, stay connected with Internet with free WiFi, or enjoy movies on the DVD Player/Cable TV. Kitchen is fully equipped for cooking and baking. Leave refreshed, relaxed and recharged. The home comes with a King size bed, a Queen bed, a pair of twin beds. Sofa can be used as a bed too to let 6-7 vacationers sleep comfortably. There are flat screen TVs in all bedrooms and in the living room with 250+ cable channels. Community offers Club House, multiple community pools, Tennis courts, Game Room, Gym and miles of scenic walkways,
  • 4 Bed 3 Bath Lake View

    Kissimmee: Cumbrian Lakes: Villa
    4 BDR • 3 BA • Sleeps 8 • #250645
    129 to 129 GBP/night
    When the pressures of life mean you want to escape to Kissimmee, unwind at this ultra-luxurious property and take time to recharge. Just recently listed following a $125k remodel in December 2019, you will soak up the facilities on offer. This home offers every luxury you could wish for. Located on a commanding position overlooking the central lake within the Cumbrian Lakes community, you can relax and enjoy the sunshine as the visiting wildlife gently intrudes on the peaceful tranquility of this gated community.
  • Villa Close to Disney

    Kissimmee: Lindfields: Villa
    4 BDR • 3 BA • Sleeps 8 • #227340
    99 to 139 USD/night
    This beautiful single storey villa is in the established Lindfields development of Kissimmee, located close to Disney. The property is deceptively large and has a living area over 2,200 sq ft, not including the garage and pool area. The property has 4 large bedrooms and 2 large sitting rooms, a dining area and separate breakfast area with an en-suite master bathroom and 2 further bathrooms. There is a kitchen and laundry room, both equipped to the highest standard. Outside there is a large heated South West facing swimming pool, backing onto a woodland conservation area, with pool chairs and sun loungers. Ideal for the lazy days or to relax after a day at a theme park or shopping. The pool itself is approx 30ft long and is 6 ft deep at the deep end. Phone calls: We offer free phone calls to US and Canada landlines and mobiles and to UK landlines. We also have free wireless internet access.
  • Beautiful 5 Bed, 3.5 Bath

    Kissimmee: Sunset Lakes: Villa in a gated community
    5 BDR • 4 BA • Sleeps 10 • #258984
    289 to 359 USD/night
    Beautiful 5 Bed, 3.5 Bath South Facing Lake View Villa ~ Just 5 mins from Disney* * 5 Bed, 3.5 Bath ~ Fabulous Vacation Home ~ Sleeps 10 guests + Infants * Affordable Accommodation ~ Value for Money * Just 5 minutes’ drive from Walt Disney World’s Animal Kingdom * Private South Facing Pool with Beautiful Lake View ~ Quiet Location Yet Close to Amenities * Great for Families or Groups * Spacious Living and High-Quality Comforts * Offering the Privacy Needed for Proper Relaxation Villa Overview: Our villa, located in the ideally situated community of Sunset Lakes, offers you and your party the unique opportunity to spend your Florida vacation in a quiet rural setting, yet only a short drive away from the theme parks, restaurants, shopping malls and all the many attractions Orlando has to offer. Sunset Lakes is situated off the more desirable 192 West and offers easy access to Interstate I-4, which is the gateway to all the theme parks and Orlando Attractions. Our villa offers the ultimate in rest, relaxation and great value – You’ll love the luxury of being able to pop back to the villa to enjoy a midday dip in the pool. Ticking all the boxes: • Genuinely Just 5 minutes from Disney’s Animal Kingdom Theme Park and Disney’s Blizzard Beach Water Park ~ This enviable location is surrounded by conservation areas and natural lakes • This Attractive, two story charming villa provides guests with a home from home in the sun. There’s plenty of room to stretch out and relax away from the excitement and bustle of the parks • Private South Facing Pool with 30ft x 15 seasonally heated pool ~ not overlooked by neighbours • Beautiful Lake View from the spacious extended deck ~ no looking at neighbours or walls/fences at breakfast! • All Day Sunshine on the patio, making the most of the Florida sun on the especially in the shorter winter months. (We do have shade on our patio for children and those who do not like too much sun) • Homely atmosphere and a good family choice for your stay in Orlando • A Traditional Floridian, family friendly home that is stylishly decorated and very well appointed with excellent facilities. This villa has spacious living accommodation that ultimately provides you with an enjoyable and comfortable stay Location Sunset Lakes is located just off the main 192 West. Disney World Resort is approx. 5 minutes’ drive. Universal Studios Wet ‘N’ Wild, Sea World and the International Drive area 15–20-minute drive. There are many, many fabulous golf courses within a 5-minute drive. It’s just a hop, skip and jump to some of Orlando’s finest shopping, dining and entertainment venues. Orlando International Airport is 30 minutes’ drive. Sanford Airport is 1-hour drive. The fabulous beaches of the Gulf Coast are 1.5 hours’ drive away and the Atlantic beaches are 1 hour away.
  • Air-Conditioned Game-Room

    Kissimmee: Emerald Island: Villa in a gated community
    7 BDR • 5 BA • Sleeps 16 • #201533
    275 to 500 USD/night
    3 Miles from Disney in exclusive Emerald Island gated resort community * Air-conditioned game room with pool table, air hockey, foosball and large screen TV * 7 bedrooms, 4.5 bathrooms * 2 Master suites with King size beds, 2 Queen Bedrooms and 3 themed kids rooms * Large 40' x 23' pool area * South facing pool deck * Deep 40' x 10' screened lanai with fans * No per person charge * Free supply of gas for the grill * High quality linens and towels provided * Free secure wired/wireless internet * Free phone calls within US and to many countries* Full-size crib and an extra Pack ‘n Play* Large LCD TVs in every bedroom, family room and game room (9 total) * Wii with many games * Video Games and books * Kids movie library * 24x7 Monitored Security * Accommodates up to 16 guests comfortably * Fully equipped kitchen * Separate Family and Living Rooms * Close to many golf courses and shopping centers * Discounts for last minute and multi-week stays
  • Private Cul De Sac Lot

    Kissimmee: Windsor Palms: Villa
    4 BDR • 3 BA • Sleeps 8 • #201087
    182 to 243 USD/night
    This spacious and beautifully appointed villa will be ideal for your vacation. The pool is south facing and this is one of the few villas that offers a kiddy pool and a stand alone hot tub. The villa is decorated and furnished to a very high standard. Being situated on a quiet cul de sac and not overlooked to the rear, you'll enjoy great privacy during your vacation. The villa is also just a short stroll from the club house. High speed internet and all phone calls are included in the price. Child features include pool safety nets, high chair, pack n' play, stroller, PS2.
  • Only 2 Miles to Disney

    Kissimmee: Windsor Hills: Villa
    6 BDR • 4 BA • Sleeps 12 • #243120
    379 to 799 USD/night
    This is a truly luxurious vacation home at a GREAT VALUE!! Our Luxurious Villa features: • 6 bedroom 4 bath villa with private pool • Pool heating is an optional fee • 3 King Master bedrooms, 1 Queen bedroom, 2 Twin bedrooms • All bedrooms have HD TVs • FREE Baby Crib, high chair • Child Safety Pool Fence • Fully equipped kitchen with all major appliances • Wireless Internet Service • Full size washer and dryer • Full Dining room, Living Room and Great Room • Professionally decorated and furnished • Games Room with Pool Table, and Gaming TV • Very short walk to the Clubhouse • Our property manager is one of the best in the Disney area. They care about delivering excellent service as much as we do. A perfect match. This home will bring the excitement of Disney to you and have everyone talking about your trip for months to come. In addition to this beautiful home, you as our guest will have full access to the Windsor Hills clubhouse, sundry shop, resort-style pool, game room, exercise room, theater, and all other amenities at no extra cost. You are also just minutes away from shopping and restaurants.
  • Stunning Lake Views, only

    Kissimmee: Oak Island Harbor: Villa
    4 BDR • 3 BA • Sleeps 8 • #202871
    200 to 200 USD/night
    Welcome to the house by the lake, a beautiful newly renovated villa, fully air conditioned, overlooking a magnificent lake offering executive living at affordable prices. If it's relaxed living and plush surroundings that you are looking for, then this villa has it all and only 2 miles from Disney! You too can enjoy our comfortable home whilst enjoying your Disney World, Sea World, Universal Orlando and Busch Gardens vacation. The home is equipped with just about everything to make your vacation experience a memorable and enjoyable one. Close enough to everything but in a tranquil neighbourhood perfect for your relaxation.
  • Grand Premium 3bd

    Kissimmee: Lake Berkley: Townhouse in a gated community
    3 BDR • 3 BA • Sleeps 7 • #260188
    115 to 289 USD/night
    This is a lovely resort style 3BD TownHouse and is good to accommodate up to 7 people. Nature view 3 bed/3 bath, fully furnished upgraded and convenient to pool/clubhouse. This home is air-conditioned and free parking is available on site. This gated community has so much to offer and walking distance to grocery store (Walmart), many restaurants, ice cream shop, bank, pharmacy, emergency clinic and much more. Free Wi-Fi with flat-screen TVs with cable, laundry facilities are also available for added convenience. HOUSE AMENITIES: Large 3 Bedroom Home Modern Fully Equipped Kitchen WIFI Use of all Resort Facilities Flat Screen TVs Close to Disney Attractions PETS ARE ALLOWED ON REQUEST. THIS IS AN ADDITIONAL FEE OF $150. THIS IS A NON SMOKING PROPERTY. LONG TERM RENTALS ARE WELCOME.
  • Charming Home at Emerald

    Kissimmee: Emerald Island: House
    7 BDR • 5 BA • Sleeps 14 • #256182
    229 to 329 USD/night
    Emerald Island Resort is 3 Miles from Walt Disney World. Just out the main gates of Emerald Islands to the New (Jimmy Buffett) MARGARITAVILLE. It is Spacious 7 BR Home with 2 Master Suites, Game room; private Pool & Spa and on-site parking. It located in 24 hour gated community. This Vacation Resort home is everything you’re looking for your vacation stay and within a short distance from everything, and lot’s amenities. Huge Orlando vacation rental home has 7 bedrooms and 4.5 bathrooms. Great for a large Family with up to 14 guests. There are two King Master Suites, one on each floor. The master bathroom on the first floor has a walk-in shower and separate garden tub. Bedroom 3 & 4 King beds and Bedroom 5 One Queen bed. Bedroom 6 and 7 have a set of Twin beds. Each bedroom will have a TV. The family room features leather sofas, a wide screen plasma TV, DVD player and a view of the pool area, perfect for relaxing when home from the Orlando, Florida attractions. There is additional sofa seating in the front living room for entertaining. There is plenty of seating for meals with the dining room, eat in kitchen and patio table and chairs. There is tile flooring throughout the common areas. The open, spacious kitchen is perfect for cooking family meals at home. This home has a private, screened in pool and heated spa with a covered lanai to escape the sun’s rays and loungers for sunbathing along with a Gas Bar B Q Grill. The game room features a Ping Pong table, Foosball Game table and TV. Note there is no Pool table. There are additional resort amenities that are included with your stay!!!
  • Windsor Hills 6-Bed Pool

    Kissimmee: Windsor Hills: House
    6 BDR • 4 BA • Sleeps 15 • #231083
    268 to 378 USD/night
    **COVID-19 updates: we are taking extra precautions and following CDC’s cleaning guidelines before and after each rental to ensure your safe stay. Spread out and enjoy your very own sunny 6-bedroom, 4-bath pool home in the prestigious guard gated resort community of Windsor Hills just 2 miles from Disney. Newly upgraded in 2020, this charming, fun villa is loaded with 4 king beds, 1 queen bed, 2 twin beds, and 1 twin over full bunk bed, and can easily accommodate 15 people in spacious comfort. It is ideal for sharing with your extended family and friends. There is one king bedroom with its adjacent bathroom on the 1st floor. Others are on the 2nd floor. The open plan, fully equipped kitchen with breakfast area and formal dining area is perfect for sharing meals together. The private screened sparkling pool and bubbling hot spa, the shaded lanai and pool side loungers let you experience some Florida lifestyle. You and your family can have hours of fun outside and take home hundreds of happy memories under the sun. This villa features: (1) 6 bedrooms each with premium furniture, top end bedding, ceiling fan, and flat screen TV. Linens provided. (2) 4 bathrooms with hair dryers and plenty of towels. (3) Spacious family room with entertainment center, Sony Playstation II, Stereo, DVD player. (4) Formal living room. (5) Fully-equipped kitchen with all appliances and plenty of cookware. Refrigerator with water/ice maker, smooth top range, oven, microwave, dishwasher, coffee maker, toaster. (6) Breakfast table next to kitchen and breakfast bar. (7) Separate elegant dining room with 8-seat dining table. (8) Washer and dryer, vacuum cleaner, iron provided (9) Free WiFi, free phone calls to US and Canada (10) Game room completed with a pool table, a ping-pong table, football table, etc. (11) Large private screened pool and hot spa, with covered lanai, extended decking. (12) Optional BBQ grill. Optional pool / spa heating. This villa includes free access to all the resort-style amenities that Windsor Hills resort offers. Windsor Hills is a gated resort with 24 hour security. It is filled with family fun, including a luxurious water park pool with fountains and water-slides, toddler pool, a huge Olympic-size pool with tropical lagoon style, big hot spa and sundecks. The clubhouse has a video game arcade, pool table and other game tables, fitness center, a movie theatre, huge comfortable lounges, and a sundry shop. The resort has 2 tennis courts, a volleyball court, basketball court, also features a putting green and a the castle-themed kids’ playground too. Nothing in this area has what Windsor Hills has to offer. Windsor Hills resort is located in the heart of Orlando Disney area. Many restaurants and shops, groceries, medical clinics, pharmacies are all within minutes. - 30 Mins - Orlando International Airport - 2 Mins - Highway 192 (Tourist Corridor) - 2 Mins - Many restaurants and shops - 3 Mins – Supermarket, Target, Publix, Walmart, pharmacy - 5 Mins - Golf Courses - 8 Mins - Walt Disney World - 10 Mins - Cypress Gardens Adventure Park - 16 Mins - Sea World - 20 Mins - Universal Studios and Islands of Adventure - 25 mins - Florida Mall - 55 Mins - Busch Gardens - 1 hour - Gulf Coast Beaches (west & east) - 1 hour - Kennedy Space Center - 1 hour - Atlantic Beaches For golfers, there are many championship golf courses in the immediate area: Greg Norman’s development, Champions Gate, Legends course at Orange Lake, the fabulous PGA teaching courses at Orange County National. Mystic Dune is right next door to Windsor Hills!
  • Luxury 6br Windsor Hills

    Kissimmee: Windsor Hills: Villa in a gated community
    6 BDR • 4 BA • Sleeps 14 • #243119
    379 to 799 USD/night
    6 bedroom 4 bathroom 3500 sqft luxury home, located in famous Windsor Hill Resort, one of best upscale vacation home resort. It’s only 2.5 miles to Disney Theme Park and close to everywhere. It’s the BEST LOCATION. This 6 bedroom villa has 3 KING/1 QUEEN/1 FULL/3 TWIN BED and 1 Crib. All bedrooms include large LED TVs and are beautifully themed in stylish neutral tones, making them perfect for guests of all ages. We use high quality, ultra comfortable mattresses which you can only find it in 5 stars hotel. BEST SERVICE - this home is managed by top management company at Florida. Security and satisfaction guaranteed!! Windsor Hills resort offers a lagoon style pool with a large water-slide, hot tub, air conditioned/heated game room, fitness center, movie theater, convenience shop, basketball courts, sand volleyball court, 3 themed playgrounds, putting green and tennis courts. It also offers discount tickets to theme parks and a shuttle service. This really is a dream home for guests sharing a perfect vacation in Orlando with family and friends, all at a fraction of the cost of staying in a typical hotel! - 6 luxurious bedrooms and a game room (3 king rooms, 1 queen room, 2 twins/full rooms) - Jump to Safety & Security: Gated community with 24 hour security guard - 65' 4K Smart LED TV and playstation game console - Air-Conditioned Games room with pool table, Foosball and Air Hockey - Private pool and SPA in screened lanai, with child Safety Fence. - Pool heating is an optional fee - FREE 75MB high speed WiFi internet access - FREE baby gear included (full size crib, high chair, stroller) - FREE on site parking - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Large size washer and dryer included in unit - No check in required / secure key-less entry to unit
  • Crystal Cove - Kissimmee

    Kissimmee: Crystal Cove: Condo
    4 BDR • 3 BA • Sleeps 8 • #229792
    140 to 180 USD/night
    Looking for a dream vacation. This is the perfect vacation home for you that offers all comfort and privacy you need. Beautifully furnished and contemporary decor 4 bedrooms home is very spacious and features your own private pool. This comfortable vacation home at Crystal Cove Resort will make you feel at your home away from home. With your batteries recharged after a great night sleep on the comfortable bed, you will be ready to choose among the many things to do in Orlando just minutes away. Crystal Cove guests will enjoy its close proximity to Lake Toho, dining, shopping and entertainment. Approximate driving distances: Disney World - 15 minutes Universal Studios - 20 minutes SeaWorld - 20 minutes Orlando Premium Outlets - 30 minutes Daytona Beach - 1 hour and 30 minutes Guests can ask for Pool Heat or/and BBQ. Contact us for more information. About the Condo: Crystal Cove offers guests a large clubhouse featuring a resort-style pool, a fitness center, communal kitchen and games room.
  • Grand Family Superior 3bd

    Kissimmee: Laguna Bay Villas: Apartment in a complex
    3 BDR • 3 BA • Sleeps 8 • #260038
    130 to 399 USD/night
    This is a Grand Superior 3 bedroom 3 bath condo apartment located in a gated community of Villas Of Island Club Resort only few minutes away from Disney theme parks and Universal Studios. This condo comes fully furnished, high ceilings, spacious living and dining area, galley kitchen with breakfast bar, large walk in closets in each room, 2 large master bedrooms with private bathroom, 2 bunk beds in kids bedroom. Also a nice patio that leads out to the rear of the property. This Condo has a community pool, tennis courts, grill, gym, etc. Pets are welcome on request with additional pet fee of $150. Long term rentals are welcome. THIS IS A NON SMOKING PROPERTY.
  • Beautiful Villa 4 Br/3 Ba

    Kissimmee: Lake Berkley: Villa in a gated community
    4 BDR • 3 BA • Sleeps 9 • #202509
    169 to 259 USD/night
    Beautiful and Family friendly 4 BR/3 BA pool Villa located in the popular vacation resort of "Lake Berkley" and only 10 minutes to DISNEY. Spacious light villa with 2 living and 2 dining areas, space for the whole family. BEDROOM CONFIGURATION: - 1 KING Master. Flatscreen TV, with private bath room featuring separate walk in shower and soaker tub, - 1 QUEEN Master, Flatscreen TV, with private bath (shower/tub combo) - 2 TWIN rooms with two twin beds each and a shared bath ((shower/tub combo) It also has a fully equipped kitchen and washer and dryer for your convenience. Highchair, Crib and Stroller are provided for your use. DVD collection and Library. Make sure you get time to use the community facilities which boast a Fitness Center. There is also tennis, basket ball, volleyball, table tennis and even a stocked Lake with Fishing Pier and nature walks ..... Equipment rental at the Hapimag Clubhouse. Located only 10 minutes away from Disney this is a great place to vacation!
  • Grand Family 3bd Condo

    Kissimmee: Royal Palm Bay: Apartment in a complex
    3 BDR • 2 BA • Sleeps 8 • #260187
    130 to 399 USD/night
    This is a Grand Family 3BD Condo Apartment very impressive and fully furnished with 3 bedrooms / 2 baths. It has 1,220 sqft in a quiet and safe community, the apartment has a community pool, gym, tennis court and free parking, free wifi. The large master bedroom has a queen size bed with a private master bath. The additional bedrooms feature walk in closets with a double size bed in the 2nd and 2 bunk beds in the 3rd bedroom. This condo is good to accommodate up to 8 people. This condo is located on the first floor which is perfect for disable guests. No stairs. The property has been professionally staged and decorated with high quality mattresses and Roku Tv's on each bedroom, as well as Fully Equipped Kitchen that has everything you could possibly need, you just need to bring your clothes for a fabulous vacation. You'll enjoy the convenient location of this residence just under 20 minutes from Disney World, close to Universal theme parks, Orlando's famous shopping, excellent golf courses and incredible restaurants. Pets are welcome on request with additional pet fee of $150. Long term rentals are welcome!
  • Renovated Luxury 2 Bed 2

    Kissimmee: Tuscana: Condo in a hotel
    2 BDR • 2 BA • Sleeps 6 • #258489
    93 to 98 USD/night
    Tuscana Resort combines the ambiance of a modern resort community with the elegance, comfort and beauty of traditional Mediterranean style buildings. An elevator provides convenient access to the condo, which is located within a short walking distance from the magnificent zero entry style heated swimming pool surrounded by shade cabanas, a Jacuzzi, a pool side restaurant and outside sports bar with great food at reasonable prices. There is also a game room, a 25-seat cinema to watch movies that you can rent on site, plus a fully equipped fitness room. Our 2 BR / 2 BA condo was recently renovated and furnished. Suite one has a king bed, private bathroom with tub and shower and walk-in closet along with new 42" flat screen TV and DVD player. Suite two has a queen bed with WiFi enabled 42” flat screen TV just in case you have a Netflix or Hulu account and DVD, a private bathroom with walk-in shower and walk-in closet. An additional 50” TV with DVD is located in the living room. Designed to sleep comfortably 4 adults, can also accommodate 6 when using the new queen size sleeping sofa in the living room. A new washer and dryer, laundry detergent included, with easy to operate instructions allows you to lauder anything during your stay. You are on vacation. You are not expected to wash any towels or bed linen at the end of your stay. All your every day needs can be met at the local Publix supermarket, banks and ATMs, Walgreens drugstore and 7-Eleven gas station. For the best shopping in Florida, Orlando Premium Outlet Mall, the Mall at Millenia or Florida International Mall are just a 20 minute drive away. Resort amenities: • Temperature controlled, zero entry pool with children's section and lap section for adults • Hot tub • Free Wifi throughout the property • Shade cabanas around the pool • Poolside restaurant and bar • Movie theater (seats 30) with library of movies to choose from • Fitness center • Business center • Playground • Picnic and BBQ area • Basketball • Magnetic key card for pool access • Gated Resort • FREE local calls • FREE high speed Wi-Fi internet on secure network accessible with private password inside the condo • Coded door lock • Outdoor parking next to building • Fully equipped kitchen • 42" flat screen TV in each bedroom and 50" in living room, ea. With DVD player • Large DVD library (80+) for children and adults • Formal dining area with seating for 6 (with additional seating at the breakfast bar) • Air conditioning and ceiling fans • Smoke-free and pet-free for your comfort • Additional towels and linens for longer stays • Located on 2nd floor with elevator access Bedroom/Bed Sizes: • Suite one - King with en-suite bathroom and walk-in closet • Suite two - Queen with en-suite bathroom and walk-in closet • Living area pull-out queen size sofa bed • Room darkening shades Living Area: • 50" flat screen TV • DVD Player (DVD library available for your use) • Pull-out queen size sofa bed • Books, board games and playing cards Balcony: • screened-in terrace for your comfort • Patio table and 2 chairs Laundry: • Washer and dryer (detergent included) for your personal use. • Ironing board & Iron Kitchen: • Microwave • Blender • Toaster • Oven • Dish washer • Granite counter tops • Utensils and dinnerware to serve 8 • Kitchen knives and cookware • Large fridge, ice-maker
  • Windsor Hills Luxury Villa

    Kissimmee: Windsor Hills: Villa in a gated community
    6 BDR • 4 BA • Sleeps 16 • #207232
    269 to 879 USD/night
    Our spacious family villa has just received over 30K in updates and additions in 2020/21. It features 3500 square feet of luxury living space with 6 bedrooms and 4 bathrooms which can accommodate 16 comfortably. Our private villa also offers a screened in swimming pool with hot tub and a covered patio area. You can BBQ on our gas grill while watching the kids swim in the pool. Our villa is located in the Reserve section of Windsor Hills, a gated resort. Windsor Hills resort offers a lagoon style pool with a large waterslide, hot tub, game room, fitness center, movie theater, convenience shop, basketball courts, sand volleyball court, 3 themed playgrounds, putting green and tennis courts. Our villa is located 5 minutes from Walt Disney Theme Parks and minutes from Sea World, Universal Studios, Legoland, golf and many other popular Florida attractions. Windsor Hills offers discount tickets to theme parks and a shuttle service.
  • Brand New 4 Bed 3 Bath

    Kissimmee: BellaVida: Villa
    4 BDR • 3 BA • Sleeps 8 • #127879
    135 to 185 USD/night
    Fabulous corner lot with warming decor, making you feel at home as soon as you enter. After a day at the nearby theme parks enjoy the last of the sun by sitting under the lanai which has a south west facing aspect overlooking the 30' lit pool. As well as the home theater system and games room, the Nintendo Wii will offer hours of fun for all. The resort itself boasts a 6,700 square feet clubhouse, community pool, cyber cafe, gym arcade, basketball court, volleyball nets, picnic area, lake and tot lot playground. Eateries are in abundance and a Walmart is within walking distance.
  • Great Villa on a Gated

    Kissimmee: Crystal Cove: Villa in a gated community
    4 BDR • 3 BA • Sleeps 8 • #207543
    165 to 295 USD/night
    This villa has everything you need for a memorable vacation. Decorated to a high standard, each bedroom has a flat screen TV and there is also WiFi and a DVD player. Large kitchen is fully equipped and the villa has a washer and a dryer for your laundry needs. The Master bedroom has a king size bed and the large en suite bathroom is very impressive. The walk in closet has lots of space for your convenience. The second bedroom has a queen bed and an en suite bathroom, the third bedroom has a queen bed and a shared bathroom with the fourth bedroom which has twin beds. There are 2 dining areas, the nook table can seat 4 and the dining table can seat 6 and there is also 2 breakfast bar stools. There is plenty of seating in the screened in pool area with 4 loungers and a patio table with 6 chairs. The pool and spa are a great treat after a long day and they can be heated in the cooler months for a fee.. Guests can also enjoy a large clubhouse which is directly across the road from the villa, featuring resort-style pool, fitness center, kitchen and game room. We supply a card key for the clubhouse entrance. Located on a gated resort, Disney is only a 15 minute ride and Universal and Seaworld is approximately 30 minutes and only 5 minutes to highway 192 where you will find lots of restaurants and stores.
  • Watch the Sunset. Highland

    Kissimmee: Windsor Hills: House in a gated community
    6 BDR • 1 Loft • 4 BA • Sleeps 12 • #250685
    379 to 799 USD/night
    * Fabulous HIGHLAND Greenview * PRIVATE maintained West Facing Heated Pool/Spa * 2 miles to Disney Only 2 miles from Disney world and minutes away from other attractions, this perfectly furnished and decorated 6 bedroom with a highland greenview and west-facing pool and spa is all you need. It is located in the upscale Windsor Hills Resort. By booking with us you enjoy management from a professional company, AND the resort's many INCLUSIVE facilities. The space WHY BOOK THIS PROPERTY. It is located in the 5 star gated Windsor Hills resort—OFFICIALLY the closest resort to Disney World. Disney is accessible by local roads so you can say goodbye to traffic going to and from the attractions. WHY BOOK WITH US. Because booking with us you also get complimentary access to ALL of the facilities this vacation resort has to offer—ADDED waterpark with dueling slides, tennis court, basketball court, volleyball court, Ping Pong table, toddler’s area and park. Plus, our home is one located on the highland greenview, so you can enjoy great view and privacy while swimming and enjoying the sun by the patio! ------------------------------------------------------------- Bedrooms and bathrooms: - Upstairs bedroom 1: King sized Master and pack n play with en-suite shower and tub - Upstairs bedroom 2: King sized bedroom with en-suite shower - Upstairs bedroom 3: Star Wars theme with 2 twin beds - Upstairs bedroom 4: 2 twin beds - Upstairs bedroom 5: King sized bedroom - Upstairs bathroom: Family bathroom (shower/bath combo, twin vanities) - Bedroom 6: 1 Queen sized bedroom (Ground Floor) - Downstairs bathroom with shower(Ground Floor) ------------------------------------------------------------- Main Living Area: Cozy and comfortable seating area with a leather sectional and accent chairs Laundry room is located downstairs ------------------------------------------------------------- Kitchen: Fully equipped with a 2 seat breakfast bar Refrigerator/freezer, oven, microwave, dishwasher, coffee maker, toaster, blender All utensils, cookware, dinnerware, glassware ------------------------------------------------------------- Dining: 3 Table seats 12 people 4 seat breakfast nook ------------------------------------------------------------- Entertainment: Movie Theater (110" Screen and Incredible 7.1 Surround Sound-Watch Cable Television-Movies-Play PS4-Reclining Lighted Theater Seating) - Adult Area has Large Flat Screen TV and Bumper Pool/Poker/Dining Combo Table -Dining/Activity Area has 60" TV With PS3 In-Flat Screen TVs In Every Bedroom ------------------------------------------------------------- Outdoor Living Space: West Exposure (Beautiful Sunsets) Screened in private swimming pool and spillover spa (extra charge for heating) Covered Lanai With Outdoor Dining Table Kid's safety pool fence ------------------------------------------------------------- Other Home Highlights: Ceiling Fans In Every Bedroom And On Lanai Baby Gear: High Chair and Pack N Play Guest access - EVERYTHING. Free access to ALL resort amenities - Key-less entry with secure door code for easy check in - 24/7 Local management support --------------------------------------------------------------------------------- ***Inclusive Resort Amenities*** - Huge Lagoon-Style Pool Complete with Water Slide and Hot Tub - Children's Playground - State-of-the-Art Fitness Center - Sand Volleyball - Basketball Courts - Tennis Courts - 40-seat Movie Theatre - Video Arcade - Billiards Other things to note - Optional Pool+Spa Heat is $25.00 plus tax per day. - Early check-in/ late check-out (depends on availability) is $45/hr - **Due to safety and cleanliness reasons, we do not supply BBQ grill at the house. Optional grill rental with full propane tank starting from $65 per week is available upon request Note: A starter of complimentary toilet rolls, paper towel, hand soap, dishwasher tabs, trash bags, body wash, shampoo and conditioner are provided for your initial convenience, as well as selection of current brochures and a welcome letter. Renters are then responsible for purchasing all further supplies required for the duration of their stay.
  • Monthly and Long-Term

    Kissimmee: The Villages At Mango Key: Home
    2 BDR • 2 BA • Sleeps 4 • #239819
    118 to 118 USD/night
    Lovely 2 bedroom, 2 bath, fully furnished in excellent condition. Perfectly located in the village of Fernandina, you'll be only a short golf cart (included!) drive away from the Bradenton Village Center, the Gilchrist and Manatee Recreational Centers, and the Bonifay Country Club, among others. Property comes with everything you need including wi-fi, a gas golf cart, and a propane grill. Villages activities include golf, pickle ball, tennis, pool , yoga ,tai chi, archery, billiards, etc etc etc. This home just became available but won't be available for long. Note: You may see the last day of each month as being "unavailable." This day is set aside for house cleaning. If your plans involve renting for two or more consecutive months, please contact me and I will make the cleaning day "available." Gas golf cart available for $5 per day. If use of the cart is desired, rental for entire length of stay is required. In this listing, please select "vehicle (provided by owner) rental" under "Options."
  • Fabulous 5 Bed Villa near

    Kissimmee: Emerald Island: Villa in a gated community
    5 BDR • 4 BA • Sleeps 12 • #226562
    199 to 315 USD/night
    A luxurious 5 bedroom 4 bath villa with south-facing pool situated in luxury Emerald Island Resort Orlando. Located a short distance from the popular destinations such as Disney World, SeaWorld and Universal Studios and accommodates 10-12 guests. This tastefully-decorated 5 bedroom/4 bath vacation rental is in a great location: 3 miles or 5 minutes from Disney World, close to the famous Formosa Gardens Shopping area and will surely create many memories on your next vacation. Emerald Island Resort - Villa Features •3 Miles to Disney in Emerald Island Resort •5 bedrooms, 4 bathrooms •Accommodates 12 guests •Large private south-facing pool •TVs in multiple rooms •Towels and linens provided •Fully air-conditioned •Fully equipped kitchen •Full size washer and dryer •DVD Players •Free WIFI, just bring your laptop •Surround sound system •Full size clothes washer and dryer •Pack 'n play/High chair
  • 8br Luxury Villa in

    Kissimmee: Windsor At Westside: Villa
    8 BDR • 1 Loft • 6 BA • Sleeps 20 • #243117
    478 to 849 USD/night
    **** GREAT LOCATION, STEPS TO CLUBHOUSE **** This 4,500 sq. Ft. Home is in the new Windsor at Westside Resort and just minutes from Disney. 8 bedrooms and 6 bathrooms, with 4 en-suites. Pool area with patio set and in-ground Jacuzzi. Game room with seating, pool table and foosball table. We have several homes steps to each other, perfect for large family reunions and groups. This home was professionally designed and uses only the highest quality furniture, mattresses and decorations. Features include: - 8 Luxurious Bedrooms (3 King, 1 Queen, 1 Double Queen, 2 Twins Room, 1 Full Bunk Bed) - 6 Full Bathrooms (4 en-suite) - High quality sheets,comforters and mattresses on all beds - Free High Speed 75mbps Wi-Fi throughout the home, free calls to US and Canada, - Loft with Big Screen TV, Game Console, and Pool Table - Spacious Sitting and Dining Area - Private Heated Pool and Spa * - Pool heating is an optional fee - Full access to Windsor at Westside Clubhouse - Digital Cable TV in each room - Baby gear included (baby gate, crib, high chair, stroller) - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Full sized washer and dryer included in unit - Hair dryer, ironing board & iron included - LCD TV with DVD player and Nintendo Wii gaming console - Friendly customer support from a dedicated manager throughout your stay - Gated community with 24 hour security guard - Free on site parking for up to 5 vehicles - Easy to check in. Secure Key-less entry
  • 5 Bed Rental by Emerald

    Kissimmee: Emerald Island: Villa in a gated community
    5 BDR • 4 BA • Sleeps 12 • #226563
    199 to 315 USD/night
    This tastefully-decorated 5 bedroom/3 bath vacation rental is in a great location: 3 miles or 5 minutes from Disney World, close to the famous Formosa Gardens Shopping area and will surely create many memories on your next vacation. Villa in Emerald Island Resort - Villa Features •3 Miles to Disney in Emerald Island Resort •5 bedrooms, 4 bathrooms •Accommodates 12 guests •Large private pool and spa that can be heated optionally •TVs in multiple rooms •Towels and linens provided •Fully air-conditioned •Fully equipped kitchen •Full size washer and dryer •Free WIFI, just bring your laptop •Full size clothes washer and dryer •Pack 'n play/High chair
  • Modern Pool Villa

    Kissimmee: Encantada: Townhouse in a gated community
    4 BDR • 3 BA • Sleeps 8 • #201696
    145 to 190 USD/night
    Great villa which is tastefully decorated that will sleep 8 people. The spacious Master bedroom has a king size bed and en suite bathroom. Every bedroom has a flat screen TV as well as the family room . Telephone service with free US calls and the villa has internet access. The kitchen is fully equipped and all towels and linens are provided. The pool area has a great view of the lake and there is a pathway that leads to the clubhouse. Great view from the pool overlooking the lake which has a circular path to walk around to the clubhouse and the pool can be heated in the cooler months. Conveniently located close to shops and restaurants. The on site amenities within this secure gated resort are second to none and include the 9,000+ square foot clubhouse that features a cyber café, sundry shop, exercise facility, and a lakefront gazebo. Fishing is allowed from the dock.
  • 3br 2ba Pool Villa Private

    Kissimmee: Indian Point: Villa
    3 BDR • 2 BA • Sleeps 8 • #250585
    149 to 249 USD/night
    Great 3 Bed, 2 Bath Villa with private Pool, fenced backyard, Games Area & Wi-Fi Internet Access. Sleeps 8, Close to Disney World and all the Major Theme Parks Orlando Florida Pool Area NEW - fenced backyard for your privacy. Sit back and relax around our pool with patio table and chairs & soak up the Florida sunshine. The patio door has an alarm fitted for the safety of our younger guests. Games Area Fun for all the family, our home comes with the added bonus of a fully equipped games area. Living Area The family room is furnished with a corner Sleeper Sofa, a TV and Hi-speed Internet Access is provided. Dining Area The open plan lounge leads onto the dining area, with glass topped table & 6 chairs. This makes a perfect setting for a relaxing dinner at home. Kitchen The separate kitchen with breakfast table is fully equipped with cooker, microwave, coffee maker, fridge/freezer with ice-maker, toaster, dishwasher & all kitchen utensils. Plastic-ware is provided for use around the pool. Master Bedroom and En-Suite The Master Bedroom with wooden floor has a king size bed, large walk in wardrobe, TV and ceiling fan. The en-suite has vanity unit with lights above, walk-in shower & toilet. 2nd Bedroom The 2nd bedroom with wooden floors has a queen size bed, built in wardrobes, chest of drawers, ceiling fan and TV 3rd Bedroom The 3rd bedroom with wooden floors has twin beds. Main Bathroom The Main Bathroom between the 2nd and 3rd Bedrooms has a vanity unit, toilet, bath with overhead shower. The villa also has a washing machine and tumble dryer. FREE WiFi Internet. AIR CONDITIONING/Heating throughout. *Swimming pool & deck area complete with patio furniture *Privacy Fence *HD Cable TV *Games Area with pool table, electronic darts, table football, *Kids Mickey & Minnie themed bedroom *2 sets of golf clubs *Linens & Towels supplied (Pool Heat (electric) is available at an extra cost. Please inquire with us before booking)
  • Lake View New Luxury Pool

    Kissimmee: Windsor Hills: Villa in a gated community
    5 BDR • 5 BA • Sleeps 12 • #243427
    348 to 789 USD/night
    This 5 bedroom 5 bathroom (All En-suites!!) 3000 sqft luxury home is located in famous Windsor Hill Resort, one of best upscale vacation home resort. It’s only 2.5 miles to Disney Theme Park and close to everywhere. It’s the BEST LOCATION. This 5 bedroom villa has 3 KING ROOM/1 FULL&TWIN ROOM/1 TWIN&TWIN BEDROOM and 1 Crib. All bedrooms include large LED TVs and are beautifully themed in stylish neutral tones, making them perfect for guests of all ages. We use high quality, ultra comfortable mattresses which you can only find it in 5 stars hotel. Our home is at one of the few premium location in Windsor Hills with beautiful green view, no rear neighbors. Private east-facing heated pool and SPA in screened lanai. Windsor Hills resort offers a lagoon style pool with a large water-slide, hot tub, air conditioned/heated game room, fitness center, movie theater, convenience shop, basketball courts, sand volleyball court, 3 themed playgrounds, putting green and tennis courts. It also offers discount tickets to theme parks and a shuttle service. This really is a home for guests sharing a perfect vacation in Orlando with family and friends, all at a fraction of the cost of staying in a typical hotel! - 5 luxurious bedrooms(en-suite) and a game room (3 king rooms, 1 twin/twin room, 1 twin/full room) - Safety & Security: Gated community with 24 hour security guard - 65' Smart 4K LED TV, HDTV in every room, XBox One Game Console - Games room with pool table, Foosball - Private heated pool and SPA in screened lanai - Pool heating is an optional fee - FREE 75MB high speed WiFi internet access - FREE baby gear included (full size crib, high chair, stroller) - FREE on site parking - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Large size washer and dryer included in unit - No check in required / secure key-less entry to unit - Our vacation home is managed by top property management company in Florida. To make your vacation as smooth as possible, below are some additional services to help provide both necessities and some luxury items that you may enjoy: Concierge, Hire Equipment, Grocery Delivery, Party Planning, Weddings, Private Chef, babysitting, Transportation
  • Villa in the Heart of

    Kissimmee: Windward Cay: Villa
    3 BDR • 2 BA • Sleeps 8 • #203114
    131 to 140 EUR/night
    Three bedrooms and two bathrooms, can accommodate up to 8 people. The villa has all you need to make your stay unforgettable. This luxury villa offers living room with large flat screen TV (TVs are also in each bedroom!). Wi-fi and telephone with free long distance within the US is included as well as a play station for children. Fully equipped kitchen with: micro-wave, dishwasher, refrigerator (with ice-maker and water dispenser), coffee machine, ect... Laundry room with washer and dryer. You won't be disappointed.
  • Indian Ridge Villa

    Kissimmee: Indian Ridge: House
    4 BDR • 2 BA • Sleeps 8 • #8030
    100 to 139 USD/night
    Highlights include a great location (5 minutes from Disney), a south facing pool and spa (hot tub), plenty of space, furnished to a high standard, fully air conditioned, ceiling and free standing fans for additional comfort Swimming pool is south-facing, and can be heated during winter months for an extra charge - owner will discuss at the time of booking. It is approximately 3 feet in the shallow end, and 6 feet in the deep end. The community offers a Communal swimming pool, tennis courts, and children's play area.
  • Beautiful Sunrise Villa in

    Kissimmee: Lindfields: Home
    3 BDR • 3 BA • Sleeps 8 • #238349
    183 to 200 USD/night
    Sunrise Villa is a luxurious getaway close to all major attractions in a quiet, private & gated community in the town of Kissimmee. We provide an amazing retreat for a great deal. We are only 25 minutes from the airport & a stones throw away from Walt Disney World Orlando. Sunrise Villa has the capacity to sleep 6 – 8 people, a private swimming pool with jacuzzi & much more. Located inside the small community of Lindfields Reseve you will feel far away from the hustle and bustle of Kissimmee while only being minutes away from all the prime areas.
  • Luxury 6br Windsor Hills

    Kissimmee: Windsor Hills: House
    6 BDR • 4 BA • Sleeps 12 • #244184
    379 to 799 USD/night
    Welcome to this 6 Bedrooms Home At Windsor Hills Resort With Private Pool, Game Room COMFORT & LUXURY ! You will definitely love this house. We have furnished the home to highest standard and choose only high-quality furniture and appliances - Because we understand how important for you to have all those comforts of home after a long day at Disney. You don't want to screw up your vacation by a cheap mattress or broken furniture. BEST LOCATION and AMENITIES Only a few minutes away from Disney, the most popular "Windsor Hills Resort" is simply the BEST combination of location and facilities. A huge Resort-Style Pool, Water Slides, Hot tub, Game Room, Tennis Court, Spa, Fitness Center, Theater Room, Basketball Court, etc. All of this is INCLUDED when you stay with us and is only a few minutes’ walk. And lots of extra services, such as discounted Disney tickets, shuttle to park, available at resort welcome center. WE PROVIDE EVERYTHING YOU NEED ! - East Facing Heated Pool and SPA in screened lanai, Our villa is one of the largest highland corner lots, far from neighborhood - Pool heating is an optional fee - 6 luxurious bedrooms with 3 KING/1 QUEEN/2 FULL/2 TWIN - Gated community with 24 hour security guard - Games Room with pool table, Foosball and Air Hockey - Large HD TV in every room - FREE high speed WiFi internet - FREE full size crib, high chair - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Laundry Room with full size washer and dryer, iron table - For Senior Guests: Bedroom on first floor with super comfortable mattress - Easy check in with secure key-less entry 5 STAR SERVICES. Our vacation home is professionally managed by the top Property Management Company in Windsor Hills Resort. We spend more money to get you the BEST service. Because you are our guests, we care about your vacation and we want you to be 100% satisfied with our vacation home. SAFETY & SATISFACTION GUARANTEED ! As full-time vacation home owners, we have been in this business for many years with hundreds of happy guests and 100% positive reviews. We know what you need and we care about what you think. Book from us, your satisfaction is guaranteed!
  • Grand Executive 3bd Condo

    Kissimmee: Laguna Bay Villas: Apartment in a complex
    3 BDR • 2 BA • Sleeps 6 • #250436
    109 to 250 USD/night
    This is a Grand Executive 3BD Condo Apartment very impressive and fully furnished with 3 bedrooms / 2 baths. It has 1,220 sqft in a quiet and safe community, the apartment has a community pool, gym, tennis court and free parking, free wifi. The large master bedroom has water and conservation views with a private master bath. The additional bedrooms feature walk in closets with a queen size bed in the 2nd and a twin in the 3rd bedroom. The property has been professionally staged and decorated with high quality mattresses and Roku Tv's on each bedroom, as well as Fully Equipped Kitchen that has everything you could possibly need, you just need to bring your clothes for a fabulous vacation. You'll enjoy the convenient location of this residence just under 20 minutes from Disney World, close to Universal theme parks, Orlando's famous shopping, excellent golf courses and incredible restaurants. Pets are welcome on request with additional pet fee of $120. Long term rentals are welcome!
  • Disney Contemporary-Pool

    Kissimmee: Lindfields: House
    3 BDR • 2 BA • Sleeps 12 • #224112
    149 to 289 USD/night
    This 4 bed/2 bath fully furnished 1742 sq ft now under AIR CONDITIONING Home is 4 miles from Disney. 1.Master with en-suite shower and KING Custom Designed Bed. 2nd Bedroom with Custom Wingback Queen Bed 3rd Bedroom with 4 twin Bunk beds with shared bath. 4 room (GAME ROOM ) has 3 more additional sleeping areas that is fully AIR CONDITIONING with arcade unit Private south facing screened pool (non heated) ***72 hours advance notice of paid pool heating to meet satisfactory heating preferences Fenced in "L" Shaped yard area There are plenty of Extras Please just ask ...We will do OUR best to get you what you DESIRE.
  • Disney Themed Home

    Kissimmee: Windsor At Westside: House
    7 BDR • 1 Loft • 5 BA • Sleeps 16 • #250683
    399 to 819 USD/night
    This beautiful 7 bedroom villa in Windsor At WestSide has enough space to sleep up to 16 guests in luxury. Inside features an open-plan living and dining area, a fully equipped kitchen and spacious bedrooms, including themed kids rooms. This family-friendly home also benefits from a game room and an additional living area upstairs. Outside you will find a private pool with SPA, sun-loungers and a covered lanai with an alfresco dining area. The space This impressive home is located in the popular Windsor at Westside resort, just a short drive from Disney World. With a vast selection of on-site shops, restaurants and non-stop entertainment, this vacation destination is perfect for the whole family to enjoy. The resort features an Olympic-size swimming pool with a lazy river, a children’s play area, multiple sports courts and a modern fitness suite. Guests will also have full access to a movie theater, the resort clubhouse and the popular Tiki Bar - perfect for relaxing after a busy day at the parks. *Features* - 7 Luxurious Bedrooms (2 King, 1 Queen, 2 Full/Twin room, 2 Twin/Twin Room, 1 crib) -Sleeps 16 guest - 5.5 Full Bathrooms (3 Bedrooms with Private En-Suite Bath) - Private Pool and Spa (sectional sitting couch, patio set, 4 sun loungers, child safety fence) - Game room includes: Pool Table, Foosball Table - Gourmet Kitchen - Spacious Sitting and Dining Area - Complementary high speed WiFi internet access in unit - Digital Cable TV included - Baby gear included (crib, high chair) - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Full sized washer and dryer included in unit - Hair dryer, ironing board & iron included - Friendly customer support from a dedicated manager throughout your stay - Gated community with 24 hour security guard - Free on site parking for up to 5 vehicles - Access to many resort facilities within the community **Absolutely perfect for multi-family groups, or golf groups, this property features all the comforts of home and more. Book your vacation now at this beautiful home with pool and spa located in the gorgeous Windsor at WestSide Gate Resort. Plus as our guest you get to enjoy all the amenities of the resort such as the lazy river, splash pool for the kids, 2 other large pools, tennis courts, fully equipped exercise room, on site cinema, arcade games, and family restaurant.
  • Great Villa with Private

    Kissimmee: BellaVida: Villa
    4 BDR • 3 BA • Sleeps 12 • #250660
    160 to 295 USD/night
    Fabulous villa with 4 bedrooms and 3 bathrooms, The Master bedroom has a king-size bed with an en suite bathroom, a second bedroom has a queen-size bed with an en-suite bathroom, a third bedroom has single beds with pull-out beds underneath and the fourth bedroom has double bunk beds. The villa can sleep up to 12 guests. Each bedroom has a TV and there is free wifi. The kitchen is fully equipped and includes a microwave, coffee machine, blender, toaster and panini maker and the laundry room has a washer and dryer, Located on the popular gated resort, Bella Vida has a clubhouse, gym, large resort pool and spa. Disney is only a 10-15 minute drive and Universal is a 20-30 minute drive. Close to stores and restaurants and centrally located to all the attractions.
  • Stunning South Facing Pool

    Kissimmee: Windsor At Westside: House in a gated community
    9 BDR • 1 Loft • 6 BA • Sleeps 23 • #248929
    519 to 869 USD/night
    Absolutely perfect for multi-family groups, or golf groups, this property features all the comforts of home and more. Book your vacation now at this beautiful home with pool and spa located in the gorgeous Windsor at Westside Gate Resort. Plus as our guest you get to enjoy all the amenities of the resort such as the lazy river, splash pool for the kids,2 other large pools, tennis courts, fully equipped exercise room, on site cinema, arcade games, and family restaurant The space 9BR/6BA home in Windsor At WestSide! - 9 Luxurious Bedrooms (4 King, 1 Queen/Queen, 2 Twin/Full Room, 1 Twin/Twin, 1 Twin/Full Bunk Bed) , 1 Crib, sleep for 23 people - 6 Full Bathrooms - 3 Bedrooms With Private En-Suite Bath - Loft with Big Screen TV, Pool Table, and Foosball table - Gourmet Kitchen - Spacious Sitting and Dining Area - Private Pool and Spa - Complementary high speed WiFi internet access in unit - Digital Cable TV included - Baby gear included (crib, high chair) - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Full sized washer and dryer included in unit - Hair dryer, ironing board & iron included - LCD TV with DVD player and Nintendo gaming console - Friendly customer support from a dedicated manager throughout your stay - Gated community with 24 hour security guard
  • Luxury 4 Bedroom, 3

    Kissimmee: Encantada: Townhouse in a gated community
    4 BDR • 3 BA • Sleeps 10 • #248054
    129 to 229 USD/night
    Luxury 4 Bedroom, 3 Bathroom Townhome Sleeps 10 Only 3 Mile To Walt Disney World. Townhome has its very own full size private pool and is located in the fully gated, beautiful, lush tropical gardens of Encantada. The resorts clubhouse has 2 large heated pools, a spa, business center, restaurant, fitness center, large conference room, fishing lake, playground, kids center and gaming arcade!
  • Lake View Pool Disney

    Kissimmee: Windsor At Westside: House in a gated community
    8 BDR • 1 Loft • 6 BA • Sleeps 21 • #250686
    478 to 849 USD/night
    - PRIVATE pool and spa, NO REAR NEIGHBOR WITH LAKE VIEW!! - Close to Disney - SUPER CLOSE to FREE resort amenities - In-house games room. Relax in this perfect 8 bedroom home with a PRIVATE pool and spa. This property is located within Windsor at Westside Resort, the BEST upscale luxury premium resort near Disney and everywhere. By booking with us you enjoy management from a professional managing company, AND the resort's many INCLUSIVE facilities including a WATERPARK. The space Managed and maintained by a professional managing company with assistance JUST a message away to cater to all your family’s needs, this home away from home features: - A PRIVATE pool and spa WITH LAKE VIEW, NO REAR NEIGHBORS - Disney themed rooms - A fully equipped game room - Flat screen tv with cable installed in every single bedroom - Washer and dryer - Kitchen with appliances Bedrooms and bathrooms: - Bedroom 1: Queen bedroom with en-suite shower (Ground Floor) - Bedroom 2: King sized bedroom and crib with en suite shower, tub, twin vanities (Ground Floor) - Upstairs Bedroom 3: 2 Queen sized beds with en suite shower, twin vanities - Upstairs Bedroom 4: King sized bedroom with en suite shower, twin vanities - Upstairs Bedroom 5: King sized bedroom with en suite shower - Upstairs Bedroom 6: Star Wars theme with 1 twin and 1 full, en-suite shower - Upstairs bedroom 7: Minions theme with 1 twin 1 full - Upstairs Bedroom 8: Harry Potter theme with 1 twin 1 full, bunk - Upstairs bathroom (shower, twin vanities) Main Living Area: - Spacious seating area with leather sofas - Gathering room with stylish plush sofas and a pool table - Dining table seats 14 people Laundry room is located downstairs Kitchen: - 5 countertop seats - Refrigerator/freezer, oven, microwave, dishwasher, coffee maker, toaster, blender - All utensils, cookware, dinnerware, glassware Entertainment: - Each bedroom is furnished with a flat screen TV and access to complimentary Wifi - Main living area and gathering room have large flat screen TVs - Games room has a ping pong, and foosball table Outdoor Living Space: - Screened in private swimming pool and spillover spa (optional heating), lake view - 4x sun loungers with umbrella, 6 seat patio table - 6 Seat outdoor sofa set Guest access EVERYTHING. Free access to ALL resort amenities Key-less entry with secure door code for easy check in 24/7 Local management support Other things to note POOL HEATER: Optional Pool/Spa Heat Fee: $35 per day (tax included) Please note the pool heater works thru HEAT EXCHANGE and might not function with weather near freezing temperatures. The pool heater must be turned on for the full duration of your stay. BBQ Grill We rent grill from equipment rental company. It's delivered to home with full propane. Three burners Grill is $85/week (tax included) and $15 for each additional day. Four burners Grill is $105/week (tax included) and $15 for each additional day. Please let us know which type of grill you would like to reserve
  • Luxury 5br Windsor Hills

    Kissimmee: Windsor Hills: House
    5 BDR • 5 BA • Sleeps 12 • #246624
    348 to 789 USD/night
    * STEP to Club House/Water Park 5 bedroom 5 bathroom 2500 sqft luxury home, located in famous Windsor Hill Resort, one of best upscale vacation home resort. It’s only 2.5 miles to Disney Theme Park and close to everywhere. It’s the BEST LOCATION! * This 5 bedroom villa has 3 KING/2 FULL/2 TWIN BED and 1 Crib. All bedrooms include large LED TVs and are beautifully themed in stylish neutral tones, making them perfect for guests of all ages. We use high quality, ultra comfortable mattresses which you can only find it in 5 stars hotel. * BEST SERVICE - this home is managed by top management company at Florida. Security and satisfaction guaranteed!! * Windsor Hills resort offers a lagoon style pool with a large water-slide, hot tub, air conditioned/heated game room, fitness center, movie theater, convenience shop, basketball courts, sand volleyball court, 3 themed playgrounds, putting green and tennis courts. It also offers discount tickets to theme parks and a shuttle service. This really is a dream home for guests sharing a perfect vacation in Orlando with family and friends, all at a fraction of the cost of staying in a typical hotel! - 5 luxurious bedrooms and a game room (3 king rooms, 2 twins/full rooms) - Jump to Safety & Security: Gated community with 24 hour security guard - 65' 4K Smart LED TV in living room, 42" to 46" TV in each bedroom - Games room with pool table and Foosball - Private pool and SPA in screened lanai, with child Safety Fence. Green View without rear neighborhood - Pool heating is an optional fee - FREE high speed WiFi internet access - FREE baby gear included (full size crib, high chair, stroller) - FREE on site parking - towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Large size washer and dryer included in unit - No check in required / secure key-less entry to unit
  • Disney Contemporary

    Kissimmee: Lindfields: House
    3 BDR • 2 BA • Sleeps 7 • #226100
    135 to 259 USD/night
    This 3 bed/2 bath fully furnished 1550sq ft with pool. Home is 4 miles from Disney on a reserve protected by Florida. 1.Master with en-suite shower and King Custom Designed Bed. 2.2nd Bedroom with Custom Headboard Queen Bed 3.3rd Bedroom with 1 twin Bunk beds with full bed on bottom shared bath. 4. Game Room with AIR CONDITIONING Private south facing screened pool (non heated) ***72 hours advance notice of paid pool heating to meet satisfactory heating preferences. 4 Person Hot tub separate for extra comfort. Fee for use during stay is $150.00 "L" Shaped Gated Backyard There are plenty of Extras Please just ask ...We will do OUR best to get you what you DESIRE
  • 7 Bedroom Pool Villa with

    Kissimmee: Windsor Hills: House in a gated community
    7 BDR • 4 BA • Sleeps 15 • #247646
    379 to 799 USD/night
    This is a truly luxurious vacation home at a GREAT VALUE!! Our Luxurious Villa features: • 7 bedroom 4 bath villa with private pool • Pool heating is an optional fee • 3 King bedrooms, 2 Queen bedrooms, 2 Twin/Full bedrooms • All bedrooms have HD TVs • FREE Baby Crib, high chair • Child Safety Pool Fence • Fully equipped kitchen with all major appliances • Wireless Internet Service • Full size washer and dryer • Full Dining room, Living Room and Great Room • Professionally decorated and furnished • Games Room with Pool Table, and Gaming TV • Very short walk to the Clubhouse • Our property manager is one of the best in the Disney area. They care about delivering excellent service as much as we do. A perfect match. This home will bring the excitement of Disney to you and have everyone talking about your trip for months to come. In addition to this beautiful home, you as our guest will have full access to the Windsor Hills clubhouse, sundry shop, resort-style pool, game room, exercise room, theater, and all other amenities at no extra cost. You are also just minutes away from shopping and restaurants.
  • Relaxation Home, Close to

    Kissimmee: Indian Point: Villa
    4 BDR • 3 BA • Sleeps 8 • #260367
    130 to 155 USD/night
    This is a great home in the Indian Point community. 1800 Square Feet. Located very close to Disney, Shopping, Golf and Kayaking. Newly renovated Kitchen and Bathrooms. The home has 4 bedrooms and 3 bathrooms. It comes fully furnished with towels, and linens provided. Kitchen is fully stocked with Cookware, Serveware and Cutlery. There is a private pool where pool heat is available for an additional cost. There are also tennis courts and a public pool located in the community. This home is ideal for Families looking to have a great vacation and relax. THERE ARE NO PETS ALLOWED. THIS IS A NON SMOKING PROPERTY.

Kissimmee News and Events

Visit Kissimmee.com: Start your Florida vacation in Kissimmee and the possibilities are endless. Just a quick drive south of Orlando puts you right in the middle of all the activities and attractions that turn family vacations into non-stop fun and lasting memories.
Putting you near all the best theme park destinations in the Orlando area, Walt Disney World® Resort, Universal Orlando® Resort and SeaWorld® Orlando are just a short drive from Kissimmee.
Go flying across the water on a thrilling airboat ride and discover a world alive with tropical birds, turtles and legendary alligators. Travel to Old Town or tour the brick-lined streets of Celebration, where colorful restaurants offer a variety of dining options and unique shopping possibilities. If golf is your game, Kissimmee is a vacation dream come true. Our year-round warm weather and variety of golf courses are ideal for tourism and welcome everyone from beginners to touring pros.
Whether you’re planning a family vacation, meeting, convention or just a weekend getaway with friends, we invite you to come out and play in Kissimmee…the heart of Florida.

Visit Kissimmee.com: Free events You may think you know Kissimmee. The year-round sunny weather, the theme park thrills, the exciting dinner shows, the great shopping deals, the perfect place to create lasting memories. But the locals will tell you there are even more things to do. And the best part is, some of Kissimmee’s best-kept secrets are free!
In Kissimmee, stop at the historic Courthouse, the oldest in continuous use in the State of Florida; then meander through the downtown area to see the Kissimmee Sculpture Experience. Each year artists submit their work and a dozen are selected to adorn the tree-lined streets. Then head to Lakefront Park, but be sure to check out the Monument of States along the way.
For more leisurely meandering, head to St. Cloud, dubbed "The Friendly Soldier City" for the thousands of Civil War veterans who relocated here in the early 1900s. Let the antique stores, shops, waterfront parks, and restaurants guide you along as you stroll, shop, dine, and “people watch” all at your leisure. You’ll also enjoy the neo-traditional architecture and charm of downtown Celebration, which plays host to special events on a regular basis. It also provides an inviting international dining region with a variety of restaurants all within a four-block area.
If you’re a nature lover, you’ll be interested to know that Osceola County has the largest population of nesting bald eagles in the continental U.S. It’s also one of the country's few re-introduction sites for the endangered Whooping Crane. You and your kids can spot some of these awe-inspiring birds at Lake Lizzie Nature Preserve, the Osceola County Environmental Center, and in the Wildlife Management Areas of Bull Creek, Prairie Lakes, Three Lakes, and Triple N Ranch—all Great Florida Birding Trail sites near Orlando and the Central Florida region.
Take one day of your vacation to slow down the pace and just enjoy all of the freebies that the area has to offer. You’ll discover a different side of Kissimmee … the heart of Florida.

Whether your idea of a fun night out is with food, drinks, or entertainment, you can have it all at Disney Springs’ Late Night Your Way. How about a dinner and a show? Manor Professional Wrestling Dinner Theater is perfect for tourists and locals who are fans of wrestling while enjoying the amazing meals from the Manor Kitchen. For those who want to bring home a skill after your vacation in Kissimmee, join the Cake Decorating Class every Sundays. These are just some of the happenings that you can enjoy during your stay in our Kissimmee vacation rentals.

For all events in and around Kissimmee, make sure to find out what is going on. Check the events website for the latest information ...
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