Windsor Hills

Windsor Hills is a gated community with a 24/7 manned guardhouse. It is arguably the most sought-after vacation rental community in Kissimmee because of its top-notch amenities and location to Walt Disney World. 

As owners in good standing with our HOA, all community amenities are available to our guests FREE of charge.  *There may be a refundable deposit  or minimal charge for some sports equipment to ensure their return and/or replacement.

Community Amenities

  • 2x Olympic-size swimming pool with zero-entry option
  • The pool is ADA compliant with special access equipment
  • Large 10-person hot tub near the main pool area
  • Sir Windsor Water Park with dueling slides, interactive splash zone and smaller slides for little children
  • Games room; table tennis in the foyer 
  • Fitness room
  • Movie theatre (movies are free and can be selected at the Welcome Center)
  • Tennis, basketball, volleyball and pickleball courts
  • Putting green
  • Picnic/ BBQ area
  • 3 dedicated playground areas: the Castle playground is nearest the Villa 
  • Dog run located by the sports courts (We do not allow pets)
  • EV charging station – around the corner at the sports courts
  • ATM on site
  • Internet access and computer / printing services at Welcome Center
  • The Market Place & Grill – a small convenience store selling basics, light lunches, snacks, beverages and treats
  • Festive seasonal  decorations
  • Weekly planned activities/events
  • Selfie Spots, some of which change seasonally
  • Uber, Lyft and taxi access (fees apply)

Close and Convenient

More About Our Location

*Times are approximate*

  • 5 minutes to the nearest Super Walmart: 10 minutes to the nearest Publix Grocer
  • 2 miles to the Magic Kingdom gates and within 10-15 minutes of any Disney park
  • 5 minutes to Margaritaville and  H20Live Water park
  • 5 minutes to Island Grove Wine Co. 
  • 5-30 minutes to a vast array of award-winning restaurants 
  • 10-30 minutes to a variety of golf courses, including Disney courses
  • 15 minutes to Disney Springs
  • 15 minutes to the nearest Factory Outlet shopping
  • 20 minutes to SeaWorld or Discovery Cove
  • 25 minutes to Universal Orlando
  • 25 minutes to numerous eateries and entertainment along International Drive
  • 40 minutes to Orlando International Airport
  • 40 minutes into downtown Orlando and 75 minutes into downtown Tampa for sporting or entertainment events
  • 1 hr. to Cocoa Beach and 2 hours to Clearwater/ St. Pete’s

In the heart of the tourist area