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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

Kristie Trentham 07-01-2022

Great house perfect for our family. We were on vacation, visiting Disney & Universal. This home was close to all the parks, and had lots of space. We all enjoyed the pool, game room, and the theater in the house. Very clean and well stocked. Highly recommend this home to anyone visiting the area

Alayne Garcia 15-12-2023

We were so pleased by the set up of this house. Lots of beds, bathrooms, a heated pool and movie room. It was so nice. My kids loved it, and we were so happy that we literally were approximately 20 minutes from every theme park and that is at the worst of traffic.

Heather Bilski 08-12-2022

This house was perfect in EVERY way! The location to the water park on the resort property was within walking distance. The pool was the PERFECT temperature throughout our entire stay. The beds were comfortable! My family did NOT want to leave! We also enjoyed how close it was to all of the Disney parks! EVERYTHING WAS PERFECT! We will most defiantly be staying here again!

Kim, G 04/24/23

VRBO
Amazing house!
We absolutely loved this house! There was plenty of room and the pool was perfect. It was so close to Disney, so getting to where we needed to go was perfect. The kids also loved the clubhouse across the street, with the slides and bigger pool. The property management people were so easy to get a hold of and answered all our questions quickly. We will definitely be back next year.

Barbara Jackson

06/04/2023
We loved this home and were especially happy to have a screened pool area. Perfect place to relax after busy days at Disney parks. Plenty of kitchen ware, glasses, cups etc …very clean property.

Lori Adams 20/03/2023

Our family of 6 including adult children enjoyed staying at this property! It had a bedroom and bathroom for everyone. It was nice to have quiet family time after a busy day at the parks. We would definitely stay again.

Jennifer Williams 24/02/2023

The property was just as described and work great for our group! The property was close to the parks which made it less stressful after a long day at the parks. Plus the kids love swimming in the pool!

Sharon Weber 27/01/2023

Our family couldn't have been happier with this home away from home. There was room for everyone to gather together for meals, pool side lounging and game room fun, but also for privacy when needed. The home is located in a well kept area that was perfect for walking, and the resort amenities were an added bonus. We all enjoyed out stay fully!

Millie Ballan 06/05/2023

So close to Disney and Universal and grocery shopping easy drive. We made good use of the spray park and pool on our off days this was a bonus on those super hot days. Would definitely stay again kids had a blast

Alison Swain 19/05/2023

Loved the house and our time there. Very clean and great size for us. Kitchen had tons of plates cups spoons for big groups
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