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Windward Side Beach House Rentals & Places to Stay

Find the best beach rentals in Windward Side - We found 2 exact matches

About Windward Side Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Windward Side? PickleTrip™ features more than 2 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Windward Side. Several of these vacation rentals in Windward Side are kid-friendly & family-friendly, and are near top local attraction spots, to give guests an unforgettable travel experience. PickleTrip™’s rental listings come in all shapes and sizes for large groups, friends, or couples, or wedding retreats in Windward Side.

PickleTrip™ Offers 2 holiday homes and places to stay in Windward Side. The site provides unique Airbnb, VRBO, PickleTrip-style accommodations to fit your trip or get away with your friends and family.

PickleTrip™ beachfront rentals give you the best travel experience that makes it easy to find and book the best place to stay at the best destinations.

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Frequently Asked Questions About Windward Side Beach Rentals

There are a lot of options in Windward Side. If you plan on staying in the Windward Side 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 Side:

The average cost for a beach rental in Windward Side is $191 per night. PickleTrip has a wide assortment of great beachfront homes near Windward Side that would suit your needs.
Yes, we have 2 beach rentals with pools available in Windward Side. Check our search bar to find a selection of vacation rentals available near Windward Side.
Yes, here are the top beach rentals in Windward Side that allow you to bring your pet:

See all pet-friendly beach rentals in Windward Side on PickleTrip

Most of the beach rentals we list are suitable for families or groups. Check out the complete list of the beach houses in Windward Side to find one that works for you.
As of 2026, the data from PickleTrip shows that there are over 2 properties with private swimming pools or private homes with indoor pools in the Windward Side area.
About 2 properties in Windward Side boast of having access to hot tubs.