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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

Florida Premier Rentals

Customer Reviews

Mike Borjas 06/12/2022

Our group of 23 stayed for 6 days here. We enjoyed the amenities and location to the Disney and Universal parks.

Julia Flannery 11/10/2021

This was the perfect location! This property is not a long drive at all from Disney and very close to a lot of local restaurants/attractions. The neighborhood is very secure and nice. The house itself was tidy and spacious. Exactly what my family needed on this trip!

Elizabeth Cowan 06/11/2022

Property had everything we needed. Hoping to book again! Thanks for a great week!

Teresa DeWitt 04/06/2022

Short drive to all the theme parks. The water park/ pool in the community was great!!

Chris Dixon

02-10-2021
Good time all was well

Marietta Taylor 06/12/2022

This property is approximately 10 minutes from Disney and close to lots of restaurants, Walmart, Publix and gift shops! Allow extra travel time because traffic is heavy in the area.

John Whitcomb 31-05 2022

This house was perfect for our family. We had a couple of questions and we got super quick responses. Very easy to all of the Disney parks, SeaWorld, and the airport. My granddaughter LOVED her room, the playroom, and the pool was perfect! The only negative we have to comment on would be the air conditioning. I think that might need updating or something. It never was cool in there. We are from PA so it wasn't a big deal to us!

John Botnen 31-05 2022

Had plenty of room for the entire family. Great Home.

Cindy Saj 31-05 2022

Loved it hope to return next year

Denise Grant 31-05 2022

There were three families, 5 kids ages 3 to 10 plus adults. There was more thank enough room for all of us inside and out. Neighborhood is very nice and location to Encore is excellent. We went to the parks each day, super easy drive. Kitchen is well stocked with appliances, pots and pans. We were there for a week. We cooked most of our meals at home, if you don’t plan to do that you may not need additional items in kitchen. We bought paper supplies, toilet paper, paper hand towels, napkins, salt and paper, Tupperware, foil, seranwrap
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