1. St. Barthelemy
  2. Leeward
  3. Summer Rental

Leeward Summer Rentals, Cottages & Cabins

Book a Place to Stay in Leeward for Your Summer Getaway

About Leeward Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Leeward 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 Leeward 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 Leeward Luxury Rentals

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

In 2025, PickleTrip offers 1531 summer rentals in or around Leeward. 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 Leeward is $3,796. Check the full list of summer accommodations in Leeward.
There are 1531 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 Leeward that have a private or indoor pool:

Check all holiday rentals with a pool in Leeward on PickleTrip.

Yes, We have 1531 summer rental homes in Leeward and types of place to stay in Leeward include:

  • Vacation Homes: 1531 available for rent
  • Villas: 1531 Rentals available for rent
  • Holiday Apartments: 1531 Rentals available for rent
  • Hotels with Suites: 1531 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Leeward. 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 Leeward.