110+ Windermere Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Windermere

Discover more than 110 treehouse rentals in Windermere, perfect for your holiday adventure. Treehouse offers treetop accommodations with everything you need for a relaxing escape near Windermere, IN.

Whether you're seeking luxury multi-level treehouses, rustic forest cabins, cozy off-grid retreats, or family-friendly treehouse lodgings, we can help you find the ideal place. Our rentals feature top-notch amenities such as private decks, fully equipped kitchens, fire pits, hot tubs, and Wi-Fi, ensuring your group enjoys a comfortable and memorable stay.

Planning a group getaway to Windermere? TreeHouse guarantees a unique and unforgettable experience with plenty of options for families, large groups, or private rentals for long or short stays. Explore our Windermere pet-friendly treehouse rentals and easily book your dream treehouse vacation rental in Windermere with TreeHouse.

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Frequently Asked Questions About Windermere Holiday Rentals

There are a lot of options in Windermere. If you plan on staying in the Windermere area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Windermere:

There are many holiday rentals available in Windermere; however, here are a few of the most popular holiday homes listed in Windermere on our website:
At Treehouse Rentals most of our places to stay are perfect for families. Check out the complete list of holiday homes in Windermere to find one that works for you.
Yes, there are 110 self-catering family homes and holiday rentals in Windermere.
There are more than 110 luxury holiday homes in or near Windermere, according to 2025 data from Treehouse Rentals. Consider these homes for your next holiday:
Yes, there are 110 pet friendly rentals that are available in Windermere.