Find the best beach rentals in Windward - We found 2161 exact matches
About Windward Beach Home Rentals on Vacation Cottage
Looking for a cottage rental, lake house, or summer homes near Windward? Vacation Cottage features more than 2161 villas, beach hotels, and private rentals that are perfect for your next beach vacation. Discover luxury beach resorts and rentals that are within walking distance from Windward. Premium stays near the beach in Windward are kid-friendly & family-friendly, and are near top local attraction spots, to give guests an unforgettable travel experience. Vacation Cottage's listings come in all shapes and sizes for large groups, friends, couples, or wedding retreats in Windward.
Vacation Cottage offers 2161 high-end holiday homes, villas, and great places to stay in Windward. The site provides unique Airbnb-style accommodations as well as hotels and resorts to make your trip with friends and family something you'll never forget.
Vacation Cottage beachfront places to stay give you the best travel experience that makes it easy to find and book the best stays at the best destinations. Life is Better at the Cottage with Vacation Cottage.
Frequently Asked Questions About Windward Beach Rentals
What are the top rated Beach Home Rentals in Windward?
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:
- Anse Etoile St Barth
- Villa Paradise .
- Villa Case et Cuisine (2 bedrooms)
- Villa Dreamtime ideal for Family and Friends
- Ocean view villa suspended in peace (2 bedrooms)
- Villa La Vue
- Lodge Kaz à Sucre .
- Villa St Jean, 2 steps from Eden Rock (1 Bedroom)
- Wine Note - Elegant Villa in St Barts - Ocean Views
- Villa in St Jean - Spectacular view of the bay - Very private - 4 bedrooms
How much does it cost to rent a beach view rental home in Windward?
The average cost for a beach rental in Windward is $3,967 per night. Vacation Cottage has a wide assortment of great beachfront homes near Windward that would suit your needs.
Can I find a beach rental with a pool in Windward?
Yes, we have 2161 beach rentals with pools available in Windward. Check our search bar to find a selection of vacation rentals available near Windward.
Are there any beach rentals in Windward that allow pets?
Yes, here are the top beach rentals in Windward that allow you to bring your pet:
- Fabulous stay in modern Villa – Surrounded by nature. Special Offer
- Villa Yvantino
- Hotel Les Ondines Sur La Plage
- Blue Lagoon Villa, 4 to 7 bedrooms and 1 pool
See all pet-friendly beach rentals in Windward on Vacation Cottage
Do you have any beachfront homes in Windward that are perfect for families?
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.
Are there private rental homes in Windward that have indoor swimming pools?
As of 2026, the data from Vacation Cottage shows that there are over 2161 properties with private swimming pools or private homes with indoor pools in the Windward area.
Do any rentals in Windward have hot tubs?
About 2161 properties in Windward boast of having access to hot tubs.
