Windsor Hills, Kissimmee Vacation Rentals

Windsor Hills Info
Rent accommodation and lodging by owners in Windsor Hills with Owner Direct. We have been matching holiday guests with private vacation rental homes, chalets, and condos for short term and long term lodging since 1994.
Amenities: Gated entrance and a multi-million dollar clubhouse. Onsite convenience store and video rental. Barbecue area and RV parking. Activities: Lagoon-styled double Olympic beach-entry heated swimming pool with water slide, a water play area, Jacuzzi, a 48-seat movie theater, fitness center, pool tables, ping pong and foosball tables and a huge children's play area. Outdoor activities include basketball, tennis, baseball, and sand volleyball. Distances: Windsor Hills is located 1.5 miles from Disney World and 15 minutes from Universal and Sea World. Located on the 192 and close to local amenities, such as banks, restaurants and supermarkets. There are 2 golf courses as near as a 2 minute drive. Tampa to the west and Cocoa beach to the East are approximately a one hour drive. Orlando International is only 25 minutes away.

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15 Vacation Rentals

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  • Wow!  This is the One!  Luxurious Windsor Hills Villa with South Facing Pool

    Wow! This is the One

    Kissimmee: Windsor Hills: Villa
    • 6 BDR
    • 4 BA
    • Sleeps 14
    • #73895
    $288 to $444 USD/night Paypal
    My husband and I are from Canada and recently purchased this villa in Kissimmee, Florida so that we and our family can escape the snow and soak up some sunshine. This is why it was important to us to have a south facing pool so that no matter what time of year or what time of day, you know you are going to be getting as much sunshine as possible!! After purchasing the property, I spent some time redecorating and updating the property so it will feel like home to us when we go there. We have added many features that are only found in the most luxurious accomodations and put us a notch above what you would normally expect to find. Check out the pictures and I think you will like what you see!! NEW televisions in every bedroom NEW home theater - fully air conditioned, recliner seating, granite-topped bar, 60" t.v./surround sound NEW games room - full air conditioned, carpeted, foosball, ping pong and air hockey NEW game components - Wii, PlayStation 2, Karaoke - all with assortment of games/CD's NEW furnishings in 9 rooms NEW granite countertop in kitchen NEW 32" t.v. outside on pool deck NEW landscaping - enjoy a view of palm trees, orange trees and bird of paradise from the lanai FREE Wifi - password protected for your security FREE Local and International calls FREE safe for your use FREE baby equipment - 1 high chair,1 baby gate, 2 strollers, 1 bed rail, 1 baby listener, 1 walker FREE electric BBQ FREE library of assorted games, books and DVD's for your entertainment
  • Luxurious 6 Bedroom Windsor Hills Pool Home Only 1.5 Miles from Disney Gates!!

    Luxurious 6 Bedroom

    Kissimmee: Windsor Hills: Villa in a gated community
    • 6 BDR
    • 4 BA
    • Sleeps 13
    • #205241
    $195 to $450 USD/night Credit Card Star Rating
    Our Luxurious Villa features: • 6 bedroom 4 bath 2,812 sq feet • 2 King Master bedrooms, 1 Queen bedroom, 1 Double bedroom and 2 Twin bedrooms • Sleeping a total of 13 with our available rollaway bed • Listed by our Property Manager as a “Global Grand Collection Home”, an exclusive lineup of luxury homes with the finest furnishings and decoration. • All bedrooms have HD TVs and Blu-ray players • South-West facing Private Pool with Spa • Removable Pool Fence with pool alarm on the patio door • Fully equipped kitchen with all major appliances • Granite Countertops throughout the Villa! • Free 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, Air Hockey, and Foosball • Xbox 360, Nintendo Wii, and games • High Chair, Portable High Chair, Double and Single stroller, two bed rails, and Pack’n Play • Very short walk to the Clubhouse and the children’s playground • One of the largest lots in Windsor Hills offering more privacy! • Unlike many other villa owners, we treat this as our second home. We stay in the home a few times each year and want our family and guests to enjoy it as much as we do! • 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. Windsor Hills is a beautiful gated community just 1.5 miles (2.5 KM) from the gates of Walt Disney World. The resort offers: • Water park pool and clubhouse with fountains, waterslide, and a hot tub lagoon spa • Heated Double Olympic Size Swimming Pool with waterslide • A newly opened golf practice putting/chipping green area • Right next door to Mystic Dunes the #2 rated course in the Orlando area! • Castle themed Children's playground • State-of-the-art fitness center • Beach Volleyball court • Lighted Basketball courts • Lighted Tennis courts • 40-seat movie theatre • Video arcade and billiards • Available shuttle bus service to Walt Disney World, SeaWorld and Universal Studios (local charge applies).
  • Grand Opening!! Luxury 6br Windsor Hills Pool Villa,2 Miles Disney

    Grand Opening!! Luxury 6br

    Kissimmee: Windsor Hills: House
    • 6 BDR
    • 4 BA
    • Sleeps 14
    • #234418
    $239 to $459 USD/night Credit Card Paypal
    Welcome to this Brand New 6 Bedrooms Home At Windsor Hills Resort With Private Pool, Game Room LAST MINUTE DEAL AVAILABLE!! BRAND NEW & 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 - 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!
  • 2017 Grand Sale!! Luxury 6br Windsor Hills Pool Villa,2 Miles Disney

    2017 Grand Sale!! Luxury

    Kissimmee: Windsor Hills: House
    • 6 BDR
    • 4 BA
    • Sleeps 14
    • #234426
    $239 to $459 USD/night Credit Card Paypal
    Welcome to this Brand New 6 Bedrooms Home At Windsor Hills Resort With Private Pool, Game Room LAST MINUTE DEAL AVAILABLE!! BRAND NEW & 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 - 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!
  • Condo in a Resort Community

    Condo in a Resort

    Kissimmee: Windsor Hills: Condo
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #206775
    $75 to $195 USD/night Credit Card
    Stay in Kissimmee's latest and greatest new resort, Windsor Hills is a 24 hours guarded gated community with a large 1 acre lake located within the heart of Orlando’s premier tourist attractions. Windsor Hills boasts the closest proximity to Central Florida's theme parks. The main features include a massive multi million dollar clubhouse facility with an array of amenities including a large lagoon styled double olympic beach-entry heated swimming pool with water slide, toddler pool, fountains, waterfalls, 48 seat movie theatre, fitness center, foosball, air hockey, ping pong, video arcade, pool tables, sundry shop (convinience store) and each condo building complex has 2 elevators. The outdoor activities include basketball, tennis, sand volley ball, putting green, kids playground and even RV parking. Windsor Hills is located along North Old Lake Wilson Road, adjacent to US 192 in Kissimmee’s tourist corridor (Shopping, restaurants and souvenir shops are just 1/2 mile away). Located just 2 miles from I-4, Windsor Hills is only 1 1/2 miles to Disney, 10 minutes to Seaworld, 15 minutes to Universal Studios and 30 minutes from Orlando airport.
  • Pool View Luxury Condo at Windsor Hills

    Pool View Luxury Condo at

    Kissimmee: Windsor Hills: Condo
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #213308
    $100 to $222 USD/night Credit Card
    Our 3 bed/2 bath (1 king, 1 king, 2 twins) luxury pool view condo in the popular Windsor Hills complex is only 1 and a 1/2 miles from Disney on Old Lake Wilson Rd - off of Route 192 west of I4. Nicely decorated with all amenities and all new furnishings, new kitchen appliances, in unit washer and dryer, dishwasher, 48" flat screen TV along with VCR/DVD player in living room, TV with DVD in master bedroom and also in second bedroom, telephone with digital answering. We also have a pack-n-play, high chair, and a stroller for your use and convenience. Private screened lanai overlooking the pool and lake.
  • A Beautiful Condo In A Gorgeous Setting!

    A Beautiful Condo In A

    Kissimmee: Windsor Hills: Condo
    • 2 BDR
    • 2 BA
    • Sleeps 6
    • #104487
    $75 to $195 USD/night Credit Card
    Stay in Kissimmee's latest and greatest new resort, Windsor Hills is a 24 hours guarded gated community with a large 1 acre lake located within the heart of Orlando’s premier tourist attractions. Windsor Hills boasts the closest proximity to Central Florida's theme parks. The main features include a massive multi million dollar clubhouse facility with an array of amenities including a large lagoon styled double olympic beach-entry heated swimming pool with water slide, toddler pool, fountains, waterfalls, 48 seat movie theatre, fitness center, foosball, air hockey, ping pong, video arcade, pool tables, sundry shop (convinience store) and each condo building complex has 2 elevators. The outdoor activities include basketball, tennis, sand volley ball, putting green, kids playground and even RV parking. Windsor Hills is located along North Old Lake Wilson Road, adjacent to US 192 in Kissimmee’s tourist corridor (Shopping, restaurants and souvenir shops are just 1/2 mile away). Located just 2 miles from I-4, Windsor Hills is only 1 1/2 miles to Disney, 10 minutes to Seaworld, 15 minutes to Universal Studios and 30 minutes from Orlando airport.
  • Luxury Windsor Hills Condo Less than 1 and a 1/2 Miles to Disney

    Luxury Windsor Hills Condo

    Kissimmee: Windsor Hills: Condo
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #79490
    $75 to $195 USD/night Credit Card
    Our 3 bed/2 bath (1 king, 1 queen, 2 twins) corner luxury condo in the popular Windsor Hills complex is less then 2 miles from Disney on Old Lake Wilson Rd - off of Route 192 west of I4. Nicely decorated with all amenities and all new furnishings, new kitchen appliances, in unit washer and dryer, dishwasher, cable TV along with WIFI internet, TV in master bedroom and also in second bedroom, telephone. We also have a pack-n-play, high chair, and a stroller for your use and convenience. Private screened lanai.
  • 3 Bedroom Condo in Windsor Hills

    3 Bedroom Condo in Windsor

    Kissimmee: Windsor Hills: Condo
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #226556
    $75 to $195 USD/night Credit Card
    Our 3 bed/2 bath (1 king, 1 queen, 2 twins) corner luxury condo in the popular Windsor Hills complex is less then 2 miles from Disney - off of Route 192 west of I4. Nicely decorated with all amenities and all new furnishings, new kitchen appliances, in unit washer and dryer, dishwasher, cable TV along with WIFI internet, TV in master bedroom and also in second bedroom, telephone. We also have a pack-n-play, high chair, and a stroller for your use and convenience. Private screened lanai.
  • 3 Bedroom Windsor Hills Condo

    3 Bedroom Windsor Hills

    Kissimmee: Windsor Hills: Condo
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #226557
    $75 to $195 USD/night Credit Card
    Our 3 bed/2 bath (1 king, 1 queen, 2 twins) corner luxury condo in the popular Windsor Hills complex is less then 2 miles from Disney - off of Route 192 west of I4. Nicely decorated with all amenities and all new furnishings, new kitchen appliances, in unit washer and dryer, dishwasher, cable TV along with WIFI internet, TV in master bedroom and also in second bedroom, telephone. We also have a pack-n-play, high chair, and a stroller for your use and convenience. Private screened lanai.
  • 3 Bedroom Windsor Hills Condo

    3 Bedroom Windsor Hills

    Kissimmee: Windsor Hills: Condo
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #226558
    $75 to $195 USD/night Credit Card
    Our 3 bed/2 bath (1 king, 1 queen, 2 twins) corner luxury condo in the popular Windsor Hills complex is less then 2 miles from Disney - off of Route 192 west of I4. Nicely decorated with all amenities and all new furnishings, new kitchen appliances, in unit washer and dryer, dishwasher, cable TV along with WIFI internet, TV in master bedroom and also in second bedroom, telephone. We also have a pack-n-play, high chair, and a stroller for your use and convenience. Private screened lanai.
  • Windsor Hills Luxury Villa 6 Bed/4 Bath 5 Minutes from Disney Attractions

    Windsor Hills Luxury Villa

    Kissimmee: Windsor Hills: Villa in a gated community
    • 6 BDR
    • 4 BA
    • Sleeps 16
    • #207232
    $225 to $375 USD/night Paypal Star Rating
    Our spacious family villa 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.
  • Windsor Hills 6-Bed Pool Home at Disney's Doorstep

    Windsor Hills 6-Bed Pool

    Kissimmee: Windsor Hills: House
    • 6 BDR
    • 4 BA
    • Sleeps 14
    • #231083
    $170 to $340 USD/night Credit Card Paypal
    Spread out and enjoy your very own sunny 6-bedroom, 4-bathroom pool home in the 5-star Windsor Hills Resort. Best of all, Windsor Hills resort is the newest and closest resort community to the Walt Disney World, only 2 miles away. With charming, elegant design and decor, this luxurious home accommodates 14 people plus crib and playpen for a couple of small children in spacious, air conditioned comfort. It is ideal for sharing with your extended family and friends. This villa features: (1) 6 bedrooms each with premium furniture, ceiling fans, and digital cable TV (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) Cloth washer and dryer, vacuum cleaner, iron, linens, towels, hairdryers (9) Free WiFi, free phone calls to US and Canada (10) Game room complete with a pool table, a ping-pong table, football table, etc. (11) Large private screened pool and hot spa, with covered lanai, extended decking. Make sure you spend some of your vacation outside in the sparkling pool and bubbling spa, sit in the sun on the deck loungers, or have an afternoon tea under the shaded lanai to 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 is located in the heart of Orlando Disney area, close to everything. Many restaurants and shops are within 1 mile of the villa. Groceries, medical clinics, pharmacy 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 - 4 Mins - Walt Disney World Orlando - 5 Mins - Golf Course - 10 Mins - Cypress Gardens Adventure Park - 16 Mins - Sea World - 20 Mins - Universal Studios and Islands of Adventure - 55 Mins - Busch Gardens - 55 Mins - Gulf Coast Beaches (west & east) - 1 hour - Kennedy Space Center - 1 hour - Atlantic Beaches Golf lovers: There are many championship golf courses in the immediate area: Greg Norman’s development, Champions Gate, the fabulous PGA teaching courses at Orange County National. Disney courses: Magnolia, Palms and Osprey Ridge and Mystic Dunes (right next door to Windsor Hills!) This villa includes free access to all the resort-style amenities that Windsor Hills Resort has to offer. Windsor Hills is a gated resort with 24 hour security. It is filled with family fun, including a huge Olympic-size pool, designed to resemble a tropical lagoon, big hot spa and sundecks. Kids will love sliding down the 2-story high water slide or running through the splash-pad. The multi-million-dollar clubhouse has a video game arcade, pool table, ping-pong and other game tables, fitness center, a movie theatre, internet cafe, huge comfortable lounges, and a sundry shop. Windsor Hills has 2 tennis courts, a volleyball court, basketball court, also features a putting green and a the castle-themed kids’ playground too. Come and give your family the vacation of a lifetime when you stay at this fabulous villa!
  • Windsor Hills Offers the Closest to Disney Vacation Homes

    Windsor Hills Offers the

    Kissimmee: Windsor Hills: House in a gated community
    • 6 BDR
    • 3 BA
    • Sleeps 14
    • #209303
    $262 to $422 USD/night Credit Card Paypal
    It's only a 5 minute drive (2 traffic lights) away from the magic. There are resorts on Disney property that are farther from some of the parks than Windsor Hills.You can visit the parks in the morning, come back for a dip in the pool and be back in the parks for dinner and fireworks with ease. The other Orlando attractions like Sea World, Universal and International Drive are less than 15 minutes away. The fabulous resort clubhouse complex features: Lagoon-style pool/water park complex State-of-the-art fitness center Game room with billiards and table tennis Video arcade Grocery and sundries shop Private high-def surround sound movie theater Tennis and volleyball courts Children's playground BBQ gazebo 24-hour gated, guarded entrance For golfers, there is a course right next door and the fabulous Disney courses (as well as the championship courses at Reunion and Champions Gate) are less than 10 minutes away!
  • If You're Thinking of

    If You're Thinking of

    Kissimmee: Windsor Hills: Vacation Rental
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #232237
    Credit Card
    If you're thinking of taking a family vacation to Disney, this is the unit you want to stay in. This newly decorated 3BD/2BA lake view condo located in Kissimmee offers luxury and relaxation all wrapped in one!. If you're thinking of taking a family vacation to Disney, this is the unit you want to stay in. This newly decorated 3BD/2BA lake view condo located in Kissimmee offers luxury and relaxation all wrapped in one. The fresh and peaceful vibe that the living room offers creates the ultimate space for relaxation. A 55" SmartTV provides you and your family the ability to access all of your favorite TV shows and movies for a night in to kick back and relax. The fully equipped kitchen offers brand new stainless steel appliances and everything you need to cook up your favorite delicious meals. The dining room table offers seating for 6 and plenty of space for the entire family to enjoy a home cooked meal together. Each room in this beautiful condo offers an amazing lake view. The master bedroom offers a king size bed with a 40" SmartTV to enjoy your favorite show or flick before you turn in for the night. The second bedroom offers a king size bed as well as a 40" SmartTV. The Disney theme twin room offers a 32" TV and offers kids the perfect space to enjoy their Disney vacation. Enjoy the beautiful lake view on the balcony with your morning coffee or favorite night cap. This unit also includes a full size washer and dryer to offer you the ability to pack light for your Disney destination. Located in the Windsor Hills Resort. Just 15 minutes from Disney theme parks!
Experience the difference, no waiting
 
Experience the difference, no waiting
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International Rentals
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