2328+ Vacation Rentals & Holiday Homes in Windward |
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Windward Accommodations - Hotels & Rentals

About Windward Vacation Rentals

Discover More than 2328 Incredible Getaway Rentals Available in Windward. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Windward.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Windward, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Windward. The Average Size of Places to Stay Near Windward is 837.65 ft², with Prices Averaging US $3,127 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Windward. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Windward

Type Count
Villas 2154
Vacation Homes 106
Holiday Apartments 44
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Windward

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Windward with Online Reservations.

Weather in Windward, BL

View the weather forecast for Windward before booking your Windward Vacation Rentals to confirm your best time to go.

December - February
High 86°F       Low 73°F
March - May
High 87°F       Low 74°F
June - August
High 89°F       Low 77°F
September - November
High 90°F       Low 75°F

Activities WindwardGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World WindwardGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Saline Beach
Gouverneur Beach
Grand Cul de Sac
Petit Cul de Sac Beach
Marigot Beach
Gustavia Harbor
St. Jean Beach
Flamands Beach
St-Barth Plongee Birdy Dive Center
Lorient Beach
Colombier Beach
Corossol Beach
Anse des Cayes Beach
Fort Gustave
Inter Oceans Museum
Le P’tit Collectionneur
La Bulle Diving Center
Wall House
Plage du Grand Galet
Musee Territorial
Corossol
Plage de Public

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Quartier Lorient 372 Properties
Morne Criquet 296 Properties
Grand Cul-de-Sac 210 Properties
Anse de Toiny 185 Properties
Barriere des Quatres Vents 148 Properties
Devet 144 Properties
Gouverneur 129 Properties
Camaruche 120 Properties
Morne de Depoudre 107 Properties
Grand Cul de Sac 96 Properties
Anse du Grand Cul-de-Sac 96 Properties
Pointe Milou 93 Properties

Frequently Asked Questions About Windward?

What are the top hotels, lake houses & vacation rentals in Windward?

We provide an array of great vacation destinations in Windward. If you are looking to stay in or around the Windward area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windward:

How many Hotels & Vacation Rentals have private pools in Windward?

We have 1879 Hotels & Vacation Rentals featuring a private pool in and near Windward. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Windward is best for families?

Searching for a family-friendly getaway in Windward? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Windward?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 2328 in the Windward area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Windward.


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