2449+ Rental Villas and Private Getaways in Windward |
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Windward Villa Rentals

About Windward Vacation Rentals

There are more than 2449 incredible getaway rentals that are available in Windward. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Windward.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Windward, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Windward. Places to stay near Windward are 802.21 ft² on average, with prices averaging $4,753 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Windward. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in Windward

Type Count
Villas 2270
Vacation Homes 109
Holiday Apartments 45
Cabin Rentals 2
B&B 1
Unique Vacation Rentals 1
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Windward

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Windward with BedroomVillas.

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

Stay Near Windward's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Windward's Research Top Attractions For Your Vacation


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, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Quartier Lorient 365 Properties
Morne Criquet 306 Properties
Grand Cul-de-Sac 189 Properties
Anse de Toiny 162 Properties
Barriere des Quatres Vents 143 Properties
Gouverneur 127 Properties
Devet 123 Properties
Camaruche 108 Properties
Morne de Depoudre 105 Properties
Grand Cul de Sac 97 Properties
Anse du Grand Cul-de-Sac 97 Properties
Pointe Milou 92 Properties

Complexes around Windward, BL


Lagon 30 Properties
Estate 5 Properties
Villa Castle Rock Ocean Located Lorient Beach 12 Properties
Villa Lo 15 Properties
Dunes 14 Properties
Eclipse Villa 12 Properties
Villa Yellow Bird Ocean Located Pointe 12 Properties
Belle Etoile 11 Properties
Caro Villa 7 Properties
Villa Dasha 10 Properties
Villa Ocean Located Saint Jean 10 Properties
Apiano Villa 8 Properties
Bellevue Rooms Villa 4 Properties
Felicita Villa 7 Properties
Jade Villa 7 Properties
See More Complexes

Frequently Asked Questions About Windward?

What are the top hotels or resorts 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 vacation rentals have private pools in Windward?

We have 1990 luxury villas and vacation rentals featuriung 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 or resort 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?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 2449 in the Windward area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Windward. 


People Also Ask

There are 18 hotels in Windward and 2426 rentals

Recently Booked Hotels, Resorts, or Rentals in Windward