Winter Garden Summer Rentals, Cottages & Cabins

Book a Place to Stay in Winter Garden for Your Summer Getaway

About Winter Garden Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Winter Garden are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.

Enjoy the perfect summer vacation in Winter Garden with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.

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Frequently Asked Questions About Winter Garden Luxury Rentals

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

In 2025, PickleTrip offers 275 summer rentals in or around Winter Garden. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Winter Garden is $258. Check the full list of summer accommodations in Winter Garden.
There are 275 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PickleTrip.

Yes, here are some popular summer holiday rentals in Winter Garden that have a private or indoor pool:

Check all holiday rentals with a pool in Winter Garden on PickleTrip.

Yes, We have 275 summer rental homes in Winter Garden and types of place to stay in Winter Garden include:

  • Vacation Homes: 275 available for rent
  • Villas: 275 Rentals available for rent
  • Holiday Apartments: 275 Rentals available for rent
  • Hotels with Suites: 275 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Winter Garden. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Winter Garden.