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Windsor at Westside

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Welcome to Windsor at Westside Resort, one of the most popular resort communities in the Orlando area.

This stunning vacation rental resort community features all the popular resort amenities of its sister communities – Windsor Hills Resort and Windsor Palms Resort, AND more! An extraordinary 10,000 sq.ft. clubhouse is the centerpiece and includes a huge resort-style pool and kids splash park with water slide – perfect for families to enjoy for hours.

Windsor Westside Orlando has a full-service restaurant, Tu Casa, offering delicious entrees, enticing hors d’oeuvres and always your favorite drinks. The Windsor Westside tiki bar provides delicious libations while you listen to your favorite Jimmy Buffet song and sounds of the Caribbean. Happy Hour is from 4 pm to 7 pm daily.

With all the latest in cardio and strength building equipment, the fitness center will keep you tone while on vacation. For some friendly competition, there are volleyball courts and multi-purpose sports courts. In addition, a sundry shop is located in the clubhouse along with a video arcade. Windsor at Westside is a gated community, with an attendant, to ensure the safety of all our visiting guests.

Windsor at Westside Resort is strategically located in the Kissimmee area, with easy access to theme parks, dining, and shopping. For those who love to visit the Walt Disney World® Resort, the location is ideal as you gain easy access to all the Walt Disney World® Theme Parks via Toll Road 429 and the Western Way Blvd.

There is no better way to vacation than a rental home and Windsor at Westside is sure to impress. Windsor at Westside includes single-family pool homes in addition to multi-family townhomes. The private pool homes, with hot tubs, range in size from 6 bedrooms all the way up to 9 bedrooms – perfect for those larger groups and multi-generational travel. Many of our vacation homes have game rooms as well. Experience property management done right by Global Resort Homes!

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Windsor at Westside