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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

Pamela, H 09/28/21

Waterview Terrace
Great place
Our stay was wonderful! The home provided everything that was listed. A chair was broken in the game room and we let them know right away and they came by, picked it up and had it fixed the same day. Def will stay here again!

Schricka, J 09/09/21

The Tropicana
The Best Stay
This is the best rental I have ever had i would recommend it to anyone. The price was great as well!

Kimberly, S 06/18/21

The Waltz
Amazing!!!! Everything our family of 15 needed !!! Perfect!
Loved everything about the property ! Thank you so much for communicating so well.

Maria, A 10/29/20

The Temptation
Spacious and Fun
Loved this place and beats staying in any hotel. The house was clean and very spacious. We loved the game room!!!!

Michelle, H 05/07/21

The Tropicana
Book it now!
I honestly don’t even know where to start with this property. From the moment I walked in I knew I would never want to leave. It felt like pure luxury. The home is beautifully decorated, well laid out and comfortable for all ages. The pool was very warm so there was no bracing yourself for the shock of cold water. The Kitchen was well stocked with everything you would need to make a nice meal. This home is an absolute must whether you are staying for a romantic getaway with just your significant other or for a family with kids (we brought our 5 kids and no one was bored. Our kids are 1, 3, 8,10, and 12). We definitely will be back! Thank you for such a beautiful home and a great experience!

April, G 06/12/21

The Blue Pearl
Great size!
This place fit our family gathering perfect! Everyone enjoyed it. Great location and easy access to everything Disney. We had a need for maintenance and they were very prompt, even going above and beyond to accommodate us. The property management was also very responsive to our questions and suggestions. We would stay again.

Patrick, G 06/29/21

Licence To Chill
Wonderful
We enjoyed our stay, and easy access to Disney.

Michael, T 05/19/21

Tillies Town
Family Getaway
We were first impressed with the spaciousness and how clean the home was. It was nice to have fun activities like: ping pong, basketball and air hockey for entertainment. Most of all, the private pool was an awesome feature! Would highly recommend this home!

Cathe, W 03/14/21

The Address
So Perfect!!
We couldn't have found a better place to stay with our adult kids and grands for a vacation exploring Central Florida! Easy to get to Disney World, Orlando International Airport, Cocoa Beach, air boat ride/gator watching! The house was perfect for keeping teens/pre-teens entertained while not exploring . . . game room, theater room, pool/hot tub. Spent a bunch of time at the resort pool/water park/clubhouse too! The house is exactly as pictured and we couldn't have been more delighted!!

Michael, C 05/29/21

The Top Notch
The perfect location for my family of six. We really enjoyed our stay here. Everything was super clean, from the carpet in the floors to the sheets and the towels. Lots to do and very close to all the amusement parks. The neighborhood waterslides were great. And it was incredibly nice just to come back to the house in our private pool and hang out and play. This is a must return spot for my family. You will not be disappointed!
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