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Windward Coast Summer Rentals, Cottages & Cabins

Book a Place to Stay in Windward Coast for Your Summer Getaway

About Windward Coast Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Windward Coast 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 Windward Coast 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 Windward Coast Luxury Rentals

There are a lot of options in Windward Coast. If you plan on staying in the Windward Coast 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 Coast:

In 2025, PickleTrip offers 573 summer rentals in or around Windward Coast. 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 Coast is $807. Check the full list of summer accommodations in Windward Coast.
There are 573 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 Windward Coast that have a private or indoor pool:

Check all holiday rentals with a pool in Windward Coast on PickleTrip.

Yes, We have 573 summer rental homes in Windward Coast and types of place to stay in Windward Coast include:

  • Vacation Homes: 573 available for rent
  • Villas: 573 Rentals available for rent
  • Holiday Apartments: 573 Rentals available for rent
  • Hotels with Suites: 573 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Windward Coast. 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 Coast.