2442+ Private Villas and Holiday Rentals in Windward |
  1. St. Barthelemy
  2. Windward

Windward Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Windward

Discover more than 2442 vacation rentals available in Windward. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windward.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windward, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windward. On average, places to stay near Windward offer 803.28 ft², with nightly prices averaging $3,084.

With Casai, finding and comparing holiday rentals in Windward is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Show more
Show less

Top Accommodation Types in Windward

Type Count
Villas 2263
Vacation Homes 109
Holiday Apartments 45
Cottages 1

Use these Quick Filters to Find a Holiday Rental in Windward

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Windward.

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

Top Attractions Around Windward, BL

Casai offers a large selection of top attractions around Windward . Research things to do on your vacation before you visit Windward.


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

Other Places to Stay in Windward, BL


Quartier Lorient 428 Properties
Morne Criquet 329 Properties
Grand Cul-de-Sac 224 Properties
Anse de Toiny 197 Properties
Barriere des Quatres Vents 170 Properties
Devet 154 Properties
Gouverneur 146 Properties
Camaruche 125 Properties
Morne de Depoudre 120 Properties
Grand Cul de Sac 110 Properties
Anse du Grand Cul-de-Sac 110 Properties
Pointe Milou 103 Properties

Frequently Asked Questions About Windward?

What are the top holiday rentals in Windward?

With numerous options available in Windward, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windward:

How many holiday rentals have private pools in Windward?

Discover a selection of holiday rentals with private pools near Windward with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Windward are best for families?

If you're searching for a family-friendly holiday home in Windward, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windward:

How many Casai.com holiday rentals are available in Windward?

As of 2025, Casai boasts over 2442 properties listed in the Windward area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windward.


People Also Ask

There are 2442 Windward, BL Holiday Rentals

Recently Booked Holiday Rentals in Windward