Discover a selection of more than 10,000 vacation rentals in Windermere, FL 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 Windermere. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Windermere
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How many vacation rentals are available around Windermere, FL?

Our 2022 property listings offer a large selection of 27,338 vacation rentals around Windermere. From 18,962 house rentals to 5,987 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 Windermere?

Yes, of course. Vrbo has 18,962 Houses in Windermere. Our other popular types of vacation rentals in Windermere include:

  • Condos/Apartments: 5,987 rentals available
  • Villas: 4,472 rentals available
  • Cottages: 68 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 Windermere?

Yes, you can select your preferred vacation rental with pool among our 25,258 vacation rentals with pool available in Windermere. Please use our search bar to access the selection of vacation rentals available.