Leeward Settlement Summer Rentals, Cottages & Cabins

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

About Leeward Settlement Summer Rental on Casai.com

With 352 summer rental in or near Leeward Settlement? 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 Leeward Settlement 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 Leeward Settlement 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 Leeward Settlement.

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Frequently Asked Questions About Leeward Settlement Luxury Rentals

In 2025, Casai offers 352 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 $3,396. Check the full list of summer accommodations in Leeward Settlement.
There are 352 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Casai.com.

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 Casai.com.

Yes, We have 352 summer rental homes in Leeward Settlement and types of place to stay in Leeward Settlement include:

  • Vacation Homes: 352 available for rent
  • Villas: 352 Rentals available for rent
  • Holiday Apartments: 352 Rentals available for rent
  • Hotels with Suites: 352 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.