1. St. Barthelemy
  2. Leeward
  3. Beach Home Rentals

Leeward Beach House Rentals & Places to Stay

Find the best beach rentals in Leeward - We found 1003 exact matches

About Leeward Beach Home Rentals on PickleTrip

Looking for a pickleball stay or beach rental near Leeward? PickleTrip™ features more than 1003 pickleball stays or beach rentals that are perfect for your next holiday. Discover properties that are within walking distance away from Leeward. Several of these vacation rentals in Leeward 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.

PickleTrip™ Offers 1003 holiday homes and places to stay in Leeward. 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 Rentals

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

The average cost for a beach rental in Leeward is $4,020 per night. PickleTrip has a wide assortment of great beachfront homes near Leeward that would suit your needs.
Yes, we have 1003 beach rentals with pools available in Leeward. Check our search bar to find a selection of vacation rentals available near Leeward.
Yes, here are the top beach rentals in Leeward that allow you to bring your pet:

See all pet-friendly beach rentals in Leeward 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 to find one that works for you.
As of 2025, the data from PickleTrip shows that there are over 1003 properties with private swimming pools or private homes with indoor pools in the Leeward area.
About 1003 properties in Leeward boast of having access to hot tubs.