Windsor Hills resort vacation rentals near Disney

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Showcasing the finest rental homes at the closest to WDW resort community since 2007!

Recommended for vacation rentals by the Windsor Hills
Master Community Homeowners Association

Welcome to the preferred Windsor Hills homeowners vacation rental website. Our prime location gated community in the Florida Kissimmee Orlando area is as close to Walt Disney World as you can possibly get without actually staying there. We're almost across the street. Here you will find a very select collection of premium grade 2 and 3 bedroom condos, 3 bedroom townhomes, and 4, 5, and 6 bedroom villas to choose from. Many have their own private pools and are KID FRIENDLY!

For your protection, every single property promoted here has been verified as being who, what, and where they say they are as well as being in good community standing before we accepted them. Rent directly from solid Windsor Hills homeowners who have proven to be reputable, reliable, honest, and trustworthy.

If you are searching for a true vacation home away from home that includes many fond holiday memories at no extra charge, you have found the right website at last. There is no need to look further.

Please use the navigational menu on the left to browse our site. Click on the category's name or thumbnail image to go directly to that homeowner's own website for additional information and inquiries.


Windsor Hills main office guest relations number
For information only! Not rentals.




  Visit the website for P&M's convenience store located inside the Windsor Hills clubhouse. Delicious sandwiches and ice cold drinks for your poolside enjoyment.
Guest welcome packs of food and necessities delivered right to your Windsor Hills vacation home available!

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