Windsor Island Resort

Windsor Island Resort Rentals

Windsor Island Resort features 5 Bed Townhouses with Splash Pool and 5, 6, 7, 8, 9 and 10 Bed Detached Homes each with a private swimming pool for your Vacation Rental Holiday in Kissimmee, Orlando. All rental homes offer the very latest in spacious modern living considerably enhancing the overall guest experience.

Windsor Island Resort Clubhouse and on-site amenities are free to use for all guests in rental properties for the duration of the holiday.

Questions? Visit the top most Frequently Asked Questions about rental properties in Florida on our FAQs page

The Windsor Island Castaway Townhome design is complete with a private pool and courtyard, all in 2,271 sq. ft. of living space. The Castaway townhome unit offers vacation living at its finest. With a bedroom/bathroom combination on the first floor and two additional suites upstairs with an oversized loft, this home allows plenty of space for guests. An open kitchen allows you to entertain and gather with friends.
The Windsor Island Lakeshore and Winstone 5 Bed 4 Bath c2,500 sq. ft. models are quaint single-family vacation homes featuring oversized game rooms and loft space. The Lakeshore is a thoughtful floor plan with two owner’s suites and two to three additional bedroom suites. With two living spaces, an oversized games room and loft space make this home a great place to kick back and relax for both kids and parents alike. Add in a covered lanai with a private swimming pool and your rental home is complete - the perfect place to escape to for your holiday break.
The Windsor Island 6 Bed 4.5 Bath Hideaway 3,117 sq. ft. vacation home features dual Owner’s Suites, large covered lanai with storage space, and two separate living areas for entertaining. The Hideaway is a gorgeous family vacation home with four and a half bathrooms, so there’s plenty of space to spread out and relax. Entertaining is easy with an open kitchen and ample storage, plus a second floor loft ideal as a family games room. The first floor Owner’s Suite offers privacy and space, with a generous storage area.
The Windsor Island 7 Bed 5.5 Bath Seashore 3,281 sq. ft. home, built for fun and entertainment, comes alive when filled with family and friends. The expansive Seashore with its seven bedrooms, a comfortable loft, private courtyard, swimming pool, and open gathering room, two separate living spaces for entertaining plus plenty of storage enables you to live and entertain in style.
You will vacation in comfort with the luxurious 8 Bed 6 Bath Windsor Island Baymont and its spacious 4,034 sq. ft. with en-suite bedrooms. Relish in the openness of the new home Baymont home design when you enter the 2-story foyer and proceed to the open kitchen and gathering room. With a 12’ sliding glass door overlooking the pool and loft space upstairs, you can enjoy your vacation anywhere in the home!
The 9 Bed 6.5 Bath Windsor Island Clearwater 4,398 sq. ft. model impresses with oversized kitchen, private courtyard and pool, and 675 sq. ft. of game rooms and loft space. The expansive Clearwater vacation home is known for its impressive nine bedroom plan, easily accommodating families and guests. The owner’s suite is conveniently located on the main level, with a second suite upstairs. The outdoor kitchen option allows for outdoor entertaining in style.
The 10 Bed 8 Bath Windsor Island Clearwater Grand 4,393 sq. ft. can comfortably fit your whole family and more! Spread out in the spacious loft or come together to enjoy the open layout on the first floor. The expansive Windsor Island Clearwater Grand vacation home is the perfect place to bring family and friends! With a private owners suite on the first floor and 8 bedrooms in the loft you have plenty of room to host everyone. Enjoy your indoor/outdoor living with a Gathering Room open to the Kitchen, Dining Room and Covered Lanai.