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

Windward Summer Rentals, Cottages & Cabins

Book a Place to Stay in Windward for Your Summer Getaway

About Windward Summer Rental on StayAndPlay

Looking for the perfect summer golf trip in Windward? StayAndPlay offers a unique collection of golf villa rentals, including golf cabins, golf resorts, golf retreats, and more. Our properties are equipped with luxurious amenities such as private decks, swimming pools, hot tubs, Wi-Fi, and stunning golf course views. Whether you’re traveling with family, friends, or a larger group, our golf accommodations in Windward provide the ideal setting for an unforgettable golf vacation.

Make the most of your summer golf retreat in Windward with StayAndPlay. Our selection of golf accommodations ensures maximum comfort and relaxation. From elegant golf villas to private golf retreats and cozy golf cabins, each home offers a one-of-a-kind experience on the course. Find your perfect golf villa for the ultimate summer retreat in Windward with StayAndPlay. Ready to make your best swing? Book your dream golf escape with StayAndPlay!

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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, StayAndPlay.com offers 2584 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 $4,233. Check the full list of summer accommodations in Windward.
There are 2584 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with StayAndPlay.

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 StayAndPlay.

Yes, We have 2584 summer rental homes in Windward and types of place to stay in Windward include:

  • Vacation Homes: 2584 available for rent
  • Villas: 2584 Rentals available for rent
  • Holiday Apartments: 2584 Rentals available for rent
  • Hotels with Suites: 2584 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.