Leeward Settlement Summer Rentals, Cottages & Cabins

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

About Leeward Settlement Summer Rental on PetFriendly

With 371 place to stay in the summer or for your summer holiday, consider a summer resort or summer rental in or near Leeward Settlement. Explore all the best for your upcoming summer getaway on PetFriendly. Whether you are traveling with family, friends, or in a group to Leeward Settlement or areas nearby, PetFriendly has plenty of summer rentals to choose from. These summer rentals have private pools, beach access, bathtubs, hot tubs, indoor/outdoor pools, WiFi, nearby dog parks, luxury bedrooms, and pet-allowed environments.

Want to chill and have an amazing time in Leeward Settlement this summer? Pet Friendly summer rental homes are available to provide you with the maximum comfort you deserve. Whether you need a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Leeward Settlement, PetFriendly is your best place to have the summer of a lifetime.

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Frequently Asked Questions About Leeward Settlement Luxury Rentals

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

In 2026, PetFriendly offers 371 summer rentals in or around Leeward Settlement. 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 Settlement is $3,911. Check the full list of summer accommodations in Leeward Settlement.
There are 371 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PetFriendly.

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

Check all holiday rentals with a pool in Leeward Settlement on PetFriendly.

Yes, We have 371 summer rental homes in Leeward Settlement and types of place to stay in Leeward Settlement include:

  • Vacation Homes: 371 available for rent
  • Villas: 371 Rentals available for rent
  • Holiday Apartments: 371 Rentals available for rent
  • Hotels with Suites: 371 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Leeward Settlement. 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 Leeward Settlement.