Windward Beach House Rentals & Places to Stay

Find the best beach rentals in Windward - We found 641 exact matches

About Windward Beach Home Rentals on SunSkiResorts

Looking for a beach rental near Windward? SunSki features more than 641 beach rentals that are perfect for your next beach holiday. Discover luxury beach rentals within walking distance of Windward. Many of these vacation rentals in Windward are kid-friendly and family-friendly, and they are located near top local attractions, ensuring guests have an unforgettable travel experience. SunSki’s rental listings come in various shapes and sizes, catering to large groups, friends, couples, or wedding retreats in Windward.

SunSki offers 641 holiday homes and places to stay in Windward. The site provides unique Airbnb, VRBO, and SunSki-style accommodations to suit your trip or getaway with friends and family.

SunSki beachfront rentals provide you with the best travel experience, making it easy to find and book the perfect place to stay in the best destinations.

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Frequently Asked Questions About Windward Beach Rentals

There are a lot of options in Windward. If you plan on staying in the Windward area, consider making a reservation for a few nights at one of these properties as these have been rated the top Beach Home Rentals in Windward:

The average cost for a beach rental in Windward is $341 per night. SunSki has a wide assortment of great beachfront homes near Windward that would suit your needs.
Yes, we have 641 beach rentals with pools available in Windward. Check our search bar to find a selection of vacation rentals available near Windward.
Yes, here are the top beach rentals in Windward that allow you to bring your pet:

See all pet-friendly beach rentals in Windward on SunSkiResorts

Most of the beach rentals we list are suitable for families or groups. Check out the complete list of the beach houses in Windward to find one that works for you.
As of 2025, the data from SunSkiResorts shows that there are over 641 properties with private swimming pools or private homes with indoor pools in the Windward area.
About 641 properties in Windward boast of having access to hot tubs.