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 Casai.ca

With 3534 summer rental in or near Windward? Look no further than Casai for your upcoming summer getaway. Whether you're traveling with family, friends, or a group, we offer a wide selection of holiday homes and villas designed for the perfect summer retreat.

Our holiday homes and villas in Windward come with a range of top amenities, including private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.

Searching for a relaxing retreat in Windward to make unforgettable summer memories? Casai has you covered with a variety of options, including unique condos, luxury resorts, bungalows, cozy cabins, RVs, and cottages in Windward.

Show more
Show less

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 2026, Casai offers 3534 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 $3,862. Check the full list of summer accommodations in Windward.
There are 3534 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Casai.ca.

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 Casai.ca.

Yes, We have 3534 summer rental homes in Windward and types of place to stay in Windward include:

  • Vacation Homes: 3534 available for rent
  • Villas: 3534 Rentals available for rent
  • Holiday Apartments: 3534 Rentals available for rent
  • Hotels with Suites: 3534 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.