With Windsor Hills Official Rentals

Welcome to Windsor Hills


Welcome to Windsor Hills Official Rentals,

The official rental website for Windsor Hills

Please take a look at our fantastic resort style amenities!

The communal pool area is undergoing major refurbishment between September 2017 and May  2018. During this time, the pool could be closed, but just for a few hours.
The work being carried out should not impact your enjoyment of the pool area as the giant slide will not be closed until the new ones are in place

Officially endorsed by the Windsor Hills Community, this website takes the stress and worry out of finding the perfect holiday home for you and your family. Here, we do the work for you by showcasing some of the most luxurious vacation homes that Windsor Hills has to offer.

Book in complete confidence
Forget trawling the web into the small hours. Here you can save valuable time by browsing through our extensive list of Windsor Hills properties. Quickly and easily find a home that meets your needs.

We offer personal service: If you are unsure about anything click on the “contact us here” button

Booking through us is simple:

  • Browse through our extensive list of properties.
  • Choose a home that meets your needs.
  • Request a quote using the contact details on the page.
  • Secure your vacation dates.

For more details on booking one of our vacation properties, see how we work. Or fill in the form on the right to receive quotes from a number of homes in the categories selected. Please be sure to complete every section, including  a second choice and how many bedrooms you require .


If you have any questions or concerns, feel free to contact us here. We will get back to you asap!

A Few of our Properties:


  • This 3 bedroom condo sleeps 6, is located in Windsor Hills Community in Kissimmee near all the amusement parks. The condo has all the comforts of home in a Disney like setting. Master bedroom has a k...

  • Windsor Hills House / Ascot House sleeps up to 8 guests, with its 3 bedrooms and a pullout couch within its 1400 square feet of living space, and is complete with 3 bathrooms as well. It will become y...

  • 3 Br Townhome:  $10-$15 reduction off our normal nightly rates for 2018 bookings of 7 nights or longer

    3beds 3baths

    Welcome to Suntrap Villa. A luxury 3 bedroom rental Townhome in a prime location at Windsor Hills. When it comes to vacation homes, Suntrap Villa takes some beating. Set overlooking the natural rete...