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Windward Side Summer Rentals, Cottages & Cabins

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

About Windward Side Summer Rental on Casai.com

With 20 summer rental in or near Windward Side? 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 Side 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 Side 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 Side.

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Frequently Asked Questions About Windward Side Luxury Rentals

In 2025, Casai offers 20 summer rentals in or around Windward Side. 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 Side is $321. Check the full list of summer accommodations in Windward Side.
There are 20 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 Windward Side that have a private or indoor pool:

Check all holiday rentals with a pool in Windward Side on Casai.com.

Yes, We have 20 summer rental homes in Windward Side and types of place to stay in Windward Side include:

  • Vacation Homes: 20 available for rent
  • Villas: 20 Rentals available for rent
  • Holiday Apartments: 20 Rentals available for rent
  • Hotels with Suites: 20 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Windward Side. 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 Side.