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Windsor at Westside

Windsor  at Westside is one of Kissimmee’s newest resorts for sunshine vacations within easy reach of Orlando’s theme parks, water parks, shopping malls and attractions. Nestled in the heart of Kissimmee, this stunning gated community is centered on a huge resort-style pool and a 10,000 sq.ft Clubhouse. What’s not to like!


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Convenient location

When it comes to choosing where to stay, location is hugely important. Why stay a long drive away from all the theme parks when you could be enjoying life at Windsor Westside. It is just 5 miles from Disney’s Animal Kingdom, Blizzard Beach and Hollywood Studios with easy access along the 429 Highway and Western Way.  Disney Springs shopping and entertainment and Downtown Disney can all be reached in under 20 minutes.

You’ll want to spend time in Walt Disney World, 7 miles from your door along with  Epcot and SeaWorld. Even Orlando Airport can be reached in about 45 minutes along the I-4.


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Where to stay in Windsor Westside

This newly developed resort has some of the most luxurious vacation rentals in Orlando, each individually furnished and decorated to the highest standards. With a range of detached luxury villas from 5 to 9 bedrooms, there’s a vacation home in Windsor Westside that’s perfect for you, your family and friends – and there’s ample space to invite them all along too!

Imagine staying in a new villa in Windsor Westside with Disney-themed bedrooms to thrill young visitors. They won’t believe their eyes! Many of these spacious homes have a fully equipped games room providing hours of family fun each evening. Most luxury vacation rentals in Windsor Westwide even have their own private pool and spa for enjoying the beautiful sunny climate in your own back yard.


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Windsor at Westside amenities

Visiting Orlando theme parks and shopping malls can be expensive, but there’s plenty to keep everyone happy when you spend the day at Windsor Westside. Check out the huge resort pool with its waterslide and Lazy River. It’s all free when you rent a vacation home at Windsorr Westside. Relax on one of the sun loungers or enjoy the shade from your own private poolside cabana.

Volleyball, sports courts and a state-of-the-art fitness center provide plenty of opportunities for sports enthusiasts to keep fit and have fun. There are several premier golf courses nearby at Celebration and Championsgate for guests to enjoy a round of golf just a short drive from your Windsor Westside home.


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The massive clubhouse is the place to head for when you fancy poolside dining at the Tiki Bar. It also houses a shop and a video arcade for guests to compete on the many arcade games.

With so many high quality amenities to enjoy, why not book your next Orlando vacation at Windsor Westside and experience it for yourself!

Windsor at Westside – Location

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Customer Reviews

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Customer Reviews

Amanda Jackman 11/06/23

Sweet Tea Cottage
Perfect For Our Family
Our family, including extended family and our 11m old and 4.5 yr old had a lovely stay. We thoroughly enjoyed the back yard and the location was great. The driveway fit our three larger rental vehicles and it was easy to find and check in. We absolutely loved how close of a walk it was to the included amenities of the waterpark and the food and drinks at the adjacent bar/restaurant were great! This was our first family vacay all together from Alaska and everyone can’t stop talking about how perfect the rental was for us! It was clean and spacious. We appreciated the pool alarm too since we had little kids with us. We did have to go and purchase toilet paper, paper towels, soap and garbage bags since we stayed 6 nights and not enough were provided but that was clearly stated in the rental agreement beforehand. We had zero complaints with our stay and are already trying to coordinate another vacay here next year! Thank you!

Andrea Charters 02/10/24

The Prima Donna
The most glorious time!
We had a fantastic time in this home. 8 adults 50-63 yrs of age. Plenty of room not to get in each other's space. Beds were very comfortable. Kitchen was well appointed for up to 12 people. The chairs have some peeling of fabric which they have covered with blankets. That is from previous guests sitting on them with wet bathing suits. Didn't bother us. They were super comfy chairs and the blankets worked perfectly. Pool was magnificent and large. A gathering place everyday for the group. Pool heat is a must in the winter as the water is mighty chilly without. It was not turned on when we arrived and we paid for it ahead of time, but a quick phone call had that fixed in a jiff and it took about 24 hrs to get to max heat but it was swimmable the next morning. The fire pit was a great addition. Nights are cooler in Feb so we Sat out there at night and talked around the fire. Seat cushions have black stain on them from being left out in the weather but we just placed a towel over them and problem solved. Comfortable chairs! The pool team and lawn care folks came on Wednesday and were polite and asked permission to do there work which we had no problem with. They have a job to do. They were in and out of the backyard quickly and did not inconvenience us at all. The bedrooms were well appointed. The colour scheme of the house interior was calming and relaxing. The pool table upstairs was used often as was the fun garage games. We loved our stay here! We will be back again!

Enid Gonzalez 03/10/24

Magical Escape
Amazing
The house was as advertised and more . Everyone had space and privacy. Easy access to the parks without having to deal with I4 traffic. Close to stores, supermarkets and places to eat. Rapid response with questions or concerns from management. We will definitely will satay here again.

Amanda Bird 01/31/24

Summer Nights
Fast, Packed Getaway
A group of 11 (6 adults, 2 under 10, 3 under 3) stayed for a 5 day weekend and the house was great. The proximity to Disney World and other parts of Orlando made it easy to get around and the heated pool and hot tub were one of the major highlights for everyone. Despite there being a million things to do and see, one of the best parts was hanging out by the pool and visiting. There was space for all of us, without us being on top of each other or even having to share bathrooms. It was a great trip and the house just made it easy.

Alicia Esposito 12/07/23

Summer Nights
A magical stay!
We did a pre-holiday trip to Disney - two families, two groups of three. There was ample space for us in this gorgeous home, and the kids loved the themed rooms, bunk beds and game room. The space was impeccable and had all of the features / benefits promoted in perfect working condition. It’s a truly beautiful house that gives you the best of home and vacation. Finally, the pre-visit communication was consistent and transparent - they were always available to answer questions. When the entry code for the house didn’t work at check-in, I called the provided number and they updated the code live and we were able to enter within a minute. We can’t wait for our next trip to Disney because we know we have a beautiful and reliable space down there! Thanks to the team for helping us have an unforgettable trip.

Jacob Leibel 12/24/23

Summer Nights
Great spot great house
Close to parks, great house and amenities

Jane Paterson 12/27/23

The Melody
Excellent house for a large family; water park was fabulous, highly recommend
Loved it; comfortable beds, well equipped, great location, pool was wonderful to have along with the use of the water park.

Cindy McClure 12/12/23

The Magical Escape
Amazing Stay!!!
We loved this place! Exceeded our expectations and made our trip. We took our adult children and their significant others to Disney for an early Christmas present. This home was perfect! Plenty of space for all of us, a few worked while here and could do so easily! A wonderful stay and have recommended it to my friends and family. Thank you!!

Billie Jeanne Stewart 12/08/23

The Melody
Perfect Disney Getaway
My family and I loved our stay. The house was super clean and spacious. The layout was great! Easy travel to Disney. One of my favorite VRBO rentals!!

Melanie Jarocki 02/20/24

Summer Nights
Wonderful home for family vacation
The home was clean and had plenty of space for 9 of us. We enjoyed the pool and neighborhood. The location is about a 15-20 minute drive to Disney parks, and about 10 minutes to shopping/restaurants.
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