Rent accommodation and lodging by owners in Windsor At Westside 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: Windsor at Westside offers guests a clubhouse, resort style pool with water slide, Kiddies splash area, hot tubs, lazy river, a tiki bar, fitness center, volleyball courts, tennis court, basketball court, video arcade and outdoor covered children's play area. Activities: Enjoy the amenities the resort has to offer or venture out and enjoy the area's theme parks, restaurants and shopping. Distances: Windsor at Westside is approximately 30-40 minutes from the Orlando International Airport.

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Windsor At Westside Vacation Activities

11 Vacation Rentals

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  • **Brand New Design** 7br Luxury Pool Villa/Pool Table
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    **Brand New Design** 7br

    Kissimmee: Windsor At Westside: House
    • 7 BDR
    • 1 Loft
    • 5 BA
    • Sleeps 18
    • #247643
    209 to 725 USD/night Credit Card Paypal
    Remarkable Home with 7 BR Pool/SPA/Game, Nearby Disney Brand new luxury 7BR/5BA home in Windsor At WestSide. 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 Wesside Resort. Key Features Include: - 7 luxurious bedrooms (2 king rooms-1 with crib, 2 queen rooms, 1 twin/full room, 1 full/full room, 1 two twins/ full room) - Jump to Safety and Security: Gated community with 24 hour security guard, plus in-house alarm system connected to security company - 120" HD Projector in Loft and Living Room with 65 inch Smart LED TV - Games room with pool table, Foosball and Air Hockey - Private heated pool (extended size) and SPA in screened lanai - FREE long distance phone calls to USA, Canada - FREE high speed WiFi internet access in unit - FREE baby gear included (full-size crib, high chair) - FREE on site parking - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Full sized washer and dryer included in unit - No check in required / secure key-less entry to unit ** Pool Heat Fee $30 per day plus tax ** For safety reason, we don't put BBQ Grill onsite. But if you want, we can help you rent from professional company. It will be thoroughly cleaned and delivered with full propane starting at $65/wk. Other equipment rental is also available per request. *** Early check-in/ late check-out will subject to a fee of $45/hr
  • Brand New Luxurious Vacation Home!
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    Brand New Luxurious

    Kissimmee: Windsor At Westside: House
    • 7 BDR
    • 6 BA
    • Sleeps 16
    • #233495
    299 to 799 USD/night Paypal
    Brand new luxurious vacation home. 20 minutes to Disney, Universal Studios, Sea World, and the Convention Center are minutes away. 7 bedrooms, kid rooms themed with Harry Potter, Star Wars, frozen and Snow White. A gaming room, private parking, pool, hot tub. Beautiful clubhouse and facilities including Exercise room, tennis, kids playground, pool, lazy river and water park. Perfect vacation home for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends pets.
  • *New* 8br Luxury Villa in Windsor at Westside Free Wifi, Crib, near Disney World
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    *New* 8br Luxury Villa in

    Kissimmee: Windsor At Westside: Villa
    • 8 BDR
    • 1 Loft
    • 6 BA
    • Sleeps 20
    • #243117
    209 to 725 USD/night Credit Card Paypal Star Rating
    **** 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
  • Stunning Views with 8br Luxury Villa/Pool/Spa
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    Stunning Views with 8br

    Kissimmee: Windsor At Westside: Villa
    • 8 BDR
    • 6 BA
    • Sleeps 20
    • #245308
    199 to 725 USD/night Credit Card Paypal
    Luxury 8BR/6BA home in Windsor At WestSide. Steps to resort Club House. 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 Wesside Gate Resort. - 8 Luxurious Bedrooms (3 King, 1 Queen, 1 Double Queen, 2 Twins Room, 1 Full Bunk Bed) - 6 Full Bathrooms - 8 Luxurious Bedrooms (3 King, 1 Queen, 1 Double Queen, 2 Twins Room, 1 Full Bunk Bed) - 6 Full Bathrooms - 3 Bedrooms With Private En-Suite Bath - Loft with Big Screen TV, Game Console, and Pool Table - Gourmet Kitchen - Spacious Sitting and Dining Area - Private Pool and Spa - Free long distance phone calls to USA, Canada, and Mexico - Complementary high speed WiFi internet access in unit - Digital Cable TV included - 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 Other things to note - Optional Pool Heat is $30.00 plus tax per day. - Optional BBQ Gas Grill with full Propane tank is $65 for one week. - Early check-in/ late check-out will subject to a fee of $45/hr
  • **Brand New Design** 9br Luxury Pool Villa/Pool Table
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    **Brand New Design** 9br

    Kissimmee: Windsor At Westside: House
    • 9 BDR
    • 1 Loft
    • 6 BA
    • Sleeps 23
    • #247642
    209 to 725 USD/night Credit Card Paypal
    Remarkable Home with 9 BR Pool/SPA/Game, Nearby Disney Brand new luxury 9BR/6BA home in Windsor At WestSide. 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 Wesside Resort. Key Features Include: - 9 luxurious bedrooms (4 king rooms-1 with crib, 1 queen/queen room, 3 twin/full rooms, 1 twin/twin room) - Jump to Safety and Security: Gated community with 24 hour security guard, plus in-house alarm system connected to security company - 120" HD Projector in Loft and Living Room with 65 inch Smart LED TV - Games room with pool table, Foosball and Air Hockey - Private heated pool (extended size) and SPA in screened lanai - FREE long distance phone calls to USA, Canada - FREE high speed WiFi internet access in unit - FREE baby gear included (full-size crib, high chair) - FREE on site parking - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Full sized washer and dryer included in unit - No check in required / secure key-less entry to unit ** Pool Heat Fee $30 per day plus tax ** For safety reason, we don't put BBQ Grill onsite. But if you want, we can help you rent from professional company. It will be thoroughly cleaned and delivered with full propane starting at $65/wk. Other equipment rental is also available per request. *** Early check-in/ late check-out will subject to a fee of $45/hr
  • Kissimmee Windsor at Westside Resort 7br Pool/Spa Vacation Home Gameroom Karaoke
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    Kissimmee Windsor at

    Kissimmee: Windsor At Westside: Villa in a gated community
    • 7 BDR
    • 6 BA
    • Sleeps 16
    • #233281
    230 to 400 USD/night Credit Card Star Rating
    **Save. Pool heat is included and there's no service/booking/resort/credit card/ or WiFi fees, insurance/damage deposit. Rates just reduced for all of 2019!* Kissimmee's Windsor At Westside vacation rental 7 bedroom home. Disney nearby. We've been asked to name our dream home and we choose "the second star to the right" after Peter Pan's Neverland a place where you never grow up. Windsor at Westside is a new spectacular gated resort community. The amazing world class 10,000 sf clubhouse is only a few steps away. The clubhouse features a bar, serving food/drinks, lazy river, huge zero entry resort pool, aquapark, lake/pier, cabanas, sundries shop, sports courts, gym, playground, arcade, and activities and special events for more fun in the sun. Our home is designated as a Grand Collection villa. Professionally decorated and furnished, exceptionally beautiful home has 7 bedrooms 4 kings, 5 1/2 baths, 2 large living rooms one upstairs and the other downstairs, fully applianced open kitchen with island seating and dining area, pantry, W/D 1st floor, ceiling fans, heated lit pool/ spa in the screened lanai withTV table/chairs/lounges, PlayStation4, poker table-chips, board games, linens, blow dryers and iron/board. The luxurious Master king bedroom ensuite on the first floor is a must for those who have trouble with stairs. The access from there to and from the pool area and bath is brilliant. The additional 1/2 bath downstairs helps to get everybody out. There are 11 smart wall mounted TVs 2 are 60" and one TV is outside. We loved stepping outside, the kids in the pool, having our morning coffee-tea in the sun and watching the morning news. Bubble away in the hot spa after a long day in the parks, looking for that second star to the right. Then there is the full sized game room. The game room features a stage, karaoke machine, cordless/corded microphones, karaoke CD/Gs collection, TV, and a PA Bluetooth speaker system. The TV can display lyrics, so that you can all sing along, if you dare.YouTube to find tunes/lyrics. There's a Megatouch game system bar table-chairs DJ lighting pool and air hockey. The Megatouch touchscreen has over 100 games, 1-4 players, and has always been a hit for young and old. For the children there's 2 porta cribs, a stroller and highchair, stair gate, and child pool safety fence. Our home is minutes away from Disney World, and Universal, Sea World, water parks, and Old Town are all close by. Great golf, shopping, outlets, fine dinning are as well. Championsgate golf voted #1 in Orlando nearby. Groceries, pharmacies, liquor, ice cream, coffee, pizza and McDonalds are very convenient. Tampa Hardrock Casino an hour away if your feeling lucky. No pets. No smoking in the home/game room, permitted in the lanai. Cleaning fee is $200.13.5% tax on all costs. 43-5 STAR REVIEWS. ALREADY ALL 11 of 11 THIS YEAR are 5 STAR. LOVE LOVE LOVE THIS HOUSE! ... Absolutely beautiful planning to stay next year..... FANTASTIC HOME FOR A LARGE FAMILY GROUP. Definitely stay again LOVED IT ...5 couples had a ball. OMG!!!!..This house is AMAZING!!.. INSERT ANY AND ALL CLICHE DESCRIPTIONS of AMAZING. DOESN'T GET BETTER THAN THIS. Stayed on some very lovely homes.... But this home was by far the best. Our family has vacationed in Kissimmee as renters for years and renting a dream home has come to be a better way to spend quality time together on vacation. We hope you consider renting from us during your next trip and sincerely wish you and your family the very best experience possible.
  • **Brand New Design** 9br Luxury Pool Villa/Pool Table
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    **Brand New Design** 9br

    Kissimmee: Windsor At Westside: House
    • 9 BDR
    • 1 Loft
    • 6 BA
    • Sleeps 22
    • #247639
    199 to 725 USD/night Credit Card Paypal
    Remarkable Home with 9 BR Pool/SPA/Game, Nearby Disney Brand new luxury 9BR/6BA home in Windsor At WestSide. 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 Wesside Resort. Key Features Include: - 9 luxurious bedrooms (4 king rooms-1 with crib, 1 queen/queen room, 3 twin/full rooms, 1 twin/twin room) - Jump to Safety and Security: Gated community with 24 hour security guard, plus in-house alarm system connected to security company - 120" HD Projector in Loft and Living Room with 65 inch Smart LED TV - Games room with pool table, Foosball and Air Hockey - Private heated pool (extended size) and SPA in screened lanai - FREE long distance phone calls to USA, Canada - FREE high speed WiFi internet access in unit - FREE baby gear included (full-size crib, high chair) - FREE on site parking - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Full sized washer and dryer included in unit - No check in required / secure key-less entry to unit ** Pool Heat Fee $30 per day plus tax ** For safety reason, we don't put BBQ Grill onsite. But if you want, we can help you rent from professional company. It will be thoroughly cleaned and delivered with full propane starting at $65/wk. Other equipment rental is also available per request. *** Early check-in/ late check-out will subject to a fee of $45/hr
  • New 5 Bed Town Home New Community!
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    New 5 Bed Town Home New

    Kissimmee: Windsor At Westside: Townhouse in a gated community
    • 5 BDR
    • 4 BA
    • Sleeps 10
    • #227148
    201 to 322 USD/night Credit Card Paypal
    Your new holiday vacation home rental is a 5 Bedroom/4.5 Bath Vacation Holiday Town-Home that sleeps up to 11 guests has a private pool along with updated and modern furniture and appliances. Free Wifi, cable, local calls, and resort amenities. This home includes 1 King size bed, 1 Queen bed, and 5 single beds, In your new holiday home you will find it is fully equipped with everything you will need while on vacation. The kitchen has all new appliances, microwave, coffee maker, blender, cookware utensils, stove top and oven, dishwasher, refrigerator and freezer, and a washer and dryer. This amazing vacation home rental will have bed linens, pool and bath towels, toilet paper and a small bar of soap in every bathroom, garbage bags in every garbage can, and a small box of laundry detergent enough for 1 load of laundry. Please remember our holiday vacation home rentals are all self-catering, items placed in the home are complimentary and all you will need to buy pantry items and food. Windsor at Westside Resort is one of the newest gated resort community in the Orlando/Kissimmee area. Windsor at Westside clubhouse consists of everything fun in the sun. Fitness Center, Volleyball and all sports courts, arcade room, shops, resort-style pool with lazy river, cabanas, playground, outdoor fire place, tiki bar, and spa. Local Attractions and Theme Parks are just minutes away: Disney World Resort - 10 min. Animal Kingdom - 10 min. Epcot / MGM Studios - 15 min. Downtown Disney - 20 min Universal Studios - 30 min. Orlando International Airport - 30 min. Sanford Airport - 70 min Downtown Orlando - 25 Min
  • **Brand New Design** 9br Luxury Pool Villa/Pool Table
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    **Brand New Design** 9br

    Kissimmee: Windsor At Westside: House
    • 9 BDR
    • 1 Loft
    • 6 BA
    • Sleeps 22
    • #247640
    189 to 459 USD/night Credit Card Paypal
    Remarkable Home with 9 BR Pool/SPA/Game, Nearby Disney Brand new luxury 9BR/6BA home in Windsor At WestSide. 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 Wesside Resort. Key Features Include: - 9 luxurious bedrooms (4 king rooms-1 with crib, 1 queen/queen room, 3 twin/full rooms, 1 twin/twin room) - Jump to Safety and Security: Gated community with 24 hour security guard, plus in-house alarm system connected to security company - 120" HD Projector in Loft and Living Room with 65 inch Smart LED TV - Games room with pool table, Foosball and Air Hockey - Private heated pool (extended size) and SPA in screened lanai - FREE long distance phone calls to USA, Canada - FREE high speed WiFi internet access in unit - FREE baby gear included (full-size crib, high chair) - FREE on site parking - Fresh towels and linens included - Fully equipped dine-in kitchen with stainless appliances - Full sized washer and dryer included in unit - No check in required / secure key-less entry to unit ** Pool Heat Fee $30 per day plus tax ** For safety reason, we don't put BBQ Grill onsite. But if you want, we can help you rent from professional company. It will be thoroughly cleaned and delivered with full propane starting at $65/wk. Other equipment rental is also available per request. *** Early check-in/ late check-out will subject to a fee of $45/hr
  • Beautiful 5 Bedroom 4.5 Bath Townhome in Amazing Resort of Windor at Westside
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    Beautiful 5 Bedroom 4.5

    Kissimmee: Windsor At Westside: Townhouse in a gated community
    • 5 BDR
    • 5 BA
    • Sleeps 10
    • #248604
    130 to 265 USD/night Credit Card
    This Beautiful Townhome is located in Windsor at Westside Resort one of the newest resort communities in the Orlando/Kissimmee with easy access to the theme parks, dining and shopping. This property is just 10 miles form Main Gates of Disney Parks. 5 Bedrooms 4 .5 Bathrooms Private screened pool with covered lanai 2 Master Suites with flat screen TVs 2 Living Areas with Large flat screen TV. A large fully equipped kitchen with stainless steel appliances, including range, microwave, dishwasher and granite counters / breakfast bar. Washer and Dryer Hairdryer Iron and Ironing Board Free Internet Access Wifi BBQ Grill Pack and Play High Chair Linens and Towels provided Bedding: 2 King, 1 Queen, 4 Twin Beds Downstairs: - Fully equipped kitchen - Living room with a 50' Flat screen TV - Private screened in splash pool with covered lanai and a complete patio furniture - Pool area Half Bathroom (Toilet and sink) - Dining Area plus a breakfast bar with additional seating. - Guest Bedroom #1: Queen size bed , Flat screen TV - Guest Bathroom #1: Shower - Laundry Room: Full size washer and dryer, Iron, Ironing board Upstairs: - Master Bedroom 1: King size bed, Flat screen TV. - Master Bathroom 1: Shower - Master Bedroom 2: King size bed, Flat screen TV. - Master Bathroom 2: Shower - Guest Bedroom #3: 2 Twin beds, Flat Screen TV - Guest Bathroom #2: Shower - Guest Bedroom #4: 2 Twin beds, Flat Screen TV - Second living area with a 50' flat screen TV, chaise lounge and 4G XBox One Windsor at Westside Resort Amenities and Services include: - 10,000 sq.Ft. Clubhouse with State of the Art Fitness Center - Resort style Pool with Kids splash area - Lazy River - Tiki Bar - Fitness Center - The club contains tu Casa Bar and Lounge - Market and Deli - Arcade Games Room - Concierge - Sand Volley Court - Multi purpose court - Kids Playground
  • Relax in Style in
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    Relax in Style in

    Kissimmee: Windsor At Westside: Vacation Rental
    • 5 BDR
    • 1 Loft
    • 4.5 BA
    • Sleeps 12
    • #232241
    406 to 420 USD/night Credit Card
    Relax in style in the spectacular five bedroom 4.5 bath town home with its very own splash pool.. This 5 bedroom, 4.5 bath luxurious town home ensures everyone their own space, sleeping 12 people comfortably. Each bedroom features its own large flat screen TV. The ground floor bedroom features a queen size bed, while upstairs are four additional rooms. A master suite has a King size bed with a 48 inches smart TV and a spacious bathroom. A Guest room suite with a queen bed and a spacious bathroom. A Mickey and friends theme room for the kids with two twin beds, another room features a teen theme bedroom with two twin beds. If you need even more room, pull out the sleeper sofa in the spacious loft with a 55 inches TV. The large fully equipped kitchen features granite counter tops and stainless steel appliances. Enjoy meals together in the dining area, kitchen bar, or even outdoor patio space. The open concept floor plan allows everyone to be together, whether you are hanging out watching your favorite show on one of the 55-inch flat screen or cooking dinner. The outdoor space is perfect for entertaining. This home feature a game room with a ping-pong table and a private pool for you and the family to enjoy. Washer and dryer and free Wi-Fi are included along with access to the beautiful 10,000 square feet club house, resort style pool, lazy river, tiki bar, fitness center, sundry shop, video arcade and other amenities. Only a 10 minutes drive to Disney this luxurious town home is perfect for your vacation!
Experience the difference, no waiting
 
Experience the difference, no waiting
Toll Free USA, Canada
1.888.869.6377
Toll Free UK
0.800.249.4265
Toll Free Australia
1.800.150.197
International Rentals
1.250.469.9543