Discover a selection of 2,500 vacation rentals in Windsor Hills, Kissimmee that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $85 per night, and houses and condos are popular options for a stay in Windsor Hills. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Windsor Hills
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How many vacation rentals are available around Windsor Hills, Kissimmee?

Our 2021 property listings offer a large selection of 2,286 vacation rentals around Windsor Hills. From 1,705 house rentals to 431 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Windsor Hills?

Yes, of course. Vrbo has 1,705 Houses in Windsor Hills. Our other popular types of vacation rentals in Windsor Hills include:

  • Condos/Apartments: 431 rentals available
  • Villas: 643 rentals available
  • Studios: 53 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Windsor Hills?

Yes, you can select your preferred vacation rental with pool among our 2,147 vacation rentals with pool available in Windsor Hills. Please use our search bar to access the selection of vacation rentals available.