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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

  • attraction tickets
  • Auto Europe Car Rental
  • Florida Premier Rentals, Vacation Rentals, Kissimmee, FL

Customer Reviews

Florida Premier Rentals

Customer Reviews

Martin Wolfe 03/23/2025

Disney trip
Convenient spacious clean. Well appointed. Kids loved the pool and were in it on off days. All in all excellent place to stay.

Angela Griffith 03/24/2025

Great location to spend while in Orlando, relaxing!
This property was absolutely perfect for our family of 6 and we could have hosted more for sure!

Tina Antolik 03/29/2025

Amazing Disney Family Vacation Home
The property was exactly as described. Management was very responsive. We had a great time.

Kathy Herzog 04/04/2025

House was great, but not really set up for toddlers with the glass top tables. The Moana room was a big hit for the kids. The playground and splash pad were wonderful!

Gregory Abbink 04/02/2025

Clean, spacious and great location!
We truly enjoyed our stay- it provided lots of room for everyone and we were pleased with the cleanliness and functionality. We also felt very safe in the gated community.

Jo-Anne Perkins 03/18/2025

We really enjoyed this VRBO unit and thought it was well appointed, clean and in a good location.Staff were easy to communicate with and responsive.Definately rent this unit again, thanks!

Bob Murphy 02/28/25

Very Nice Home for a Family Stay
The home is spacious, and very well appointed. We enjoyed our stay here very much.

Sharleen Koepp 02/16/2025

It was amazing
Our family loved the private pool & hot tub. Would be nice to have float tubes and a ball especially for kids. Loved the large living/entertainment spaces & 4 bedrooms.Kitchen could have basic spices in the cupboard. Our toaster wasn’t working so called to report it & they promptly delivered a new one. Great place, close to Disney. Highly recommend.

Jacqueline Burke 02/09/2025

First Disney trip with family
Perfect place to take kids and grandkids. We had so much fun exploring what Orlando and surrounding areas have to offer.

Bridget Merceruio 02/10/2025

Weekend getaway
Great house, plenty of space, very clean and easy to use. There was limited seating in the living room area but great seating in the kitchen and a large dining room table.
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