Leeward Beach Summer Rentals, Cottages & Cabins

Book a Place to Stay in Leeward Beach for Your Summer Getaway

About Leeward Beach Summer Rental on PickleTrip

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

There are a lot of options in Leeward Beach. If you plan on staying in the Leeward Beach 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 Beach:

In 2025, PickleTrip offers 1204 summer rentals in or around Leeward Beach. 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 Beach is $2,239. Check the full list of summer accommodations in Leeward Beach.
There are 1204 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 Beach that have a private or indoor pool:

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

Yes, We have 1204 summer rental homes in Leeward Beach and types of place to stay in Leeward Beach include:

  • Vacation Homes: 1204 available for rent
  • Villas: 1204 Rentals available for rent
  • Holiday Apartments: 1204 Rentals available for rent
  • Hotels with Suites: 1204 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Leeward Beach. 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 Beach.