Windward Summer Rentals, Cottages & Cabins

Book a Place to Stay in Windward for Your Summer Getaway

About Windward Summer Rental on Treehouse Rentals

TreeHouseRentals™'s summer rentals in Windward are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch treehouse rentals 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 Windward with TreeHouseRentals™. 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 in your treehouse when you travel with TreeHouseRentals™.

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Frequently Asked Questions About Windward Luxury Rentals

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

In 2025, Treehouse.com offers 1030 summer rentals in or around Windward. 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 Windward is $322. Check the full list of summer accommodations in Windward.
There are 1030 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Treehouse Rentals.

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

Check all holiday rentals with a pool in Windward on Treehouse Rentals.

Yes, We have 1030 summer rental homes in Windward and types of place to stay in Windward include:

  • Vacation Homes: 1030 available for rent
  • Villas: 1030 Rentals available for rent
  • Holiday Apartments: 1030 Rentals available for rent
  • Hotels with Suites: 1030 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Windward. 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 Windward.