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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

Rose Hoover 04/11/2022

This place was amazing. My family of 7 seven with my 2 grandsons. There was plenty of space for all of us and the boys loved the avatar bunk beds with their own tv. They loved it. It was so close to DIsney and shops and restaurants. The theater room was very cool as well as the tropical storm came in so we watched movies. The property management people were very helpful and pleasant. We had a great time here and made some great memories and would definitely come back.

SCOTT MELE 31/10/2022

Very roomy, very well equipped. Plenty of room for everyone. This was an employee group we rented this for a trade show at the convention center. Would book again

Jamie Nagle 06/11/2022

We loved staying at this property for its proximity to Disney as well as its space. It was conveniently located. Kept us safe during Hurricane Nicole. Clean.

Andrew Adams 09/11/2022

This home was perfect for our family. We were in town to celebrate a wedding and get in and Disney time. This was close and accessible to everything we needed.

PATRICIA ORILLAC 29/10/2022

Great location. Nice neighbourhood. Close to parks in general

Samantha Badlam 10/20/2022

Excellent Property - Even Better Than Expected
This property was even better than expected. It was clean, updated, family friendly, and the rental company is extremely responsive. We looked at a lot of properties in Encore and were very pleased with this as the choice. Highly recommend.

Marlene Arenas 11/02/2022

We loved the house beautiful.

Christy Oliver 10/19/2022

The house was great. We were there in Oct. and paid extra for the spa and pool to be heated. It was well worth it!

Larry Porter 10/09/2022

This vacation was perfect loved our home.

Laura Robinson 10/13/2022

Absolutely amazing house!

Everything about this house is exceptional! It was very hard to get the kids to leave. The Mario room is crazy. Now they want it for Christmas! Good luck Santa!
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