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Windermere Beach House Rentals & Places to Stay

Find the best beach rentals in Windermere - We found 35 exact matches

About Windermere Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Windermere? PickleTrip™ features more than 35 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Windermere. Several of these vacation rentals in Windermere are kid-friendly & family-friendly, and are near top local attraction spots, to give guests an unforgettable travel experience. PickleTrip™’s rental listings come in all shapes and sizes for large groups, friends, or couples, or wedding retreats in Windermere.

PickleTrip™ Offers 35 holiday homes and places to stay in Windermere. The site provides unique Airbnb, VRBO, PickleTrip-style accommodations to fit your trip or get away with your friends and family.

PickleTrip™ beachfront rentals give you the best travel experience that makes it easy to find and book the best place to stay at the best destinations.

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Frequently Asked Questions About Windermere Beach 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 Beach Home Rentals in Windermere:

The average cost for a beach rental in Windermere is $405 per night. PickleTrip has a wide assortment of great beachfront homes near Windermere that would suit your needs.
Yes, we have 35 beach rentals with pools available in Windermere. Check our search bar to find a selection of vacation rentals available near Windermere.
Yes, here are the top beach rentals in Windermere that allow you to bring your pet:

See all pet-friendly beach rentals in Windermere on PickleTrip

Most of the beach rentals we list are suitable for families or groups. Check out the complete list of the beach houses in Windermere to find one that works for you.
As of 2026, the data from PickleTrip shows that there are over 35 properties with private swimming pools or private homes with indoor pools in the Windermere area.
About 35 properties in Windermere boast of having access to hot tubs.