Windward Islands Summer Rentals, Cottages & Cabins

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

About Windward Islands Summer Rental on Rent By Owner

With 943 summer rentals in or near Windward Islands, choosing a suitable rental home for your upcoming summer getaway on Rent By Owner is easy. Whether you are traveling with family, friends, or in a group to Windward Islands or areas nearby, RBO has plenty of summer accommodations to choose from, many with top amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxury bedrooms, bathtubs, and pet-allowed environments.

Looking for a relaxing place to stay in Windward Islands for a summer vacation you do not want to forget easily? Rent By Owner summer rental homes are available to provide you with the maximum comfort you deserve. Whether you're needing a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Windward Islands, RBO has got you covered for your next summer holiday.

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Frequently Asked Questions About Windward Islands Luxury Rentals

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

In 2025, RBO offers 943 summer rentals in or around Windward Islands. 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 Islands is $250. Check the full list of summer accommodations in Windward Islands.
There are 943 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Rent By Owner.

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

Check all holiday rentals with a pool in Windward Islands on Rent By Owner.