Leeward Islands Summer Rentals, Cottages & Cabins

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

About Leeward Islands Summer Rental on Rent By Owner

With 136 summer rentals in or near Leeward 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 Leeward 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 Leeward 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 Leeward Islands, RBO has got you covered for your next summer holiday.

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Frequently Asked Questions About Leeward Islands Luxury Rentals

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

In 2025, RBO offers 136 summer rentals in or around Leeward 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 Leeward Islands is $405. Check the full list of summer accommodations in Leeward Islands.
There are 136 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 Leeward Islands that have a private or indoor pool:

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