Windsor Cay is Kissimmee’s newest and most luxurious resort community. This stunning vacation rental community features all the popular resort amenities of its sister communities - Windsor Hills Resort and Windsor Palms Resort, AND so much more! An extraordinary 5,000 sq.ft. clubhouse is the centerpiece, as well as a huge resort-style pool, complete with cabanas, a water slide, and lazy river – perfect for families to enjoy for hours! When it’s time for a drink or a bite to eat, the tiki bar serves both your favorite libation, along with a tempting menu for poolside dining. With all the latest in cardio and strength building equipment, the fitness center will keep you in shape while on vacation. For some friendly competition, there are sand volleyball courts and a multi-purpose sports courts. In addition, a sundry shop is located in the clubhouse, along with a video arcade.
Windsor Islande is a gated community, with an attendant, to ensure the safety for all our visiting guests.

Windsor Island Resort is located in the Davenport area. Access to this “secret” near Disney entrance is just 20 minutes away and avoids the heavy traffic that can occur with the main Disney entrance.

There is no better way to vacation than a rental home, and Windsor at Island is sure to impress!

Bedroom Configuration

Bedrooms/Bed Sizes


Please note. Some of our homes may be pictured with a gas bbq grill or outdoor built in grill. If guests wish to use the grills it is the guest responsibility to clean the grill and replenish the propane tank if needed.