Leeward Beach Rentals & Places to Stay

Find the best beach rentals in Leeward Beach - We found 719 exact matches

About Leeward Beach Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Leeward Beach? PickleTrip™ features more than 719 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Leeward Beach. Several of these vacation rentals in Leeward Beach 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 Leeward Beach.

PickleTrip™ Offers 719 holiday homes and places to stay in Leeward Beach. 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 Leeward Beach Beach Rentals

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

The average cost for a beach rental in Leeward Beach is $2,257 per night. PickleTrip has a wide assortment of great beachfront homes near Leeward Beach that would suit your needs.
Yes, we have 719 beach rentals with pools available in Leeward Beach. Check our search bar to find a selection of vacation rentals available near Leeward Beach.
Yes, here are the top beach rentals in Leeward Beach that allow you to bring your pet:

See all pet-friendly beach rentals in Leeward Beach 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 Leeward Beach to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 719 properties with private swimming pools or private homes with indoor pools in the Leeward Beach area.
About 719 properties in Leeward Beach boast of having access to hot tubs.