Windward Holiday Rentals

Compare Villas, Resorts, & Rentals in Windward, St. Barthelemy

From US $912 per night
|
10.0 (3 Reviews)
2 Bedrooms 6 Guests
10.0 (76 Reviews)
1 Bedroom 2 Guests
From US $1,302 per night
10.0 (1 Review)
3 Bedrooms 6 Guests
From US $1,247 per night
|
9.8 (92 Reviews)
1 Bedroom 2 Guests
From US $594 per night
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9.8 (9 Reviews)
2 Bedrooms 4 Guests
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9.8 (77 Reviews)
1 Bedroom 2 Guests
10.0 (35 Reviews)
4 Bedrooms 8 Guests
9.5 (10 Reviews)
1 Bedroom 2 Guests
10.0 (25 Reviews)
7 Bedrooms 10 Guests
9.5 (9 Reviews)
2 Bedrooms 4 Guests
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9.5 (2 Reviews)
1 Bedroom 4 Guests
10.0 (23 Reviews)
2 Bedrooms 4 Guests
From US $287 per night
|
9.3 (11 Reviews)
1 Bedroom 2 Guests
10.0 (20 Reviews)
3 Bedrooms 6 Guests
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9.3 (9 Reviews)
2 Bedrooms 4 Guests
10.0 (20 Reviews)
1 Bedroom 2 Guests
From US $1,180 per night
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9.3 (4 Reviews)
4 Bedrooms 8 Guests
10.0 (17 Reviews)
1 Bedroom 3 Guests
From US $272 per night
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9.0 (31 Reviews)
1 Bedroom 2 Guests
From US $168 per night
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9.0 (18 Reviews)
1 Bedroom 2 Guests
10.0 (15 Reviews)
3 Bedrooms 6 Guests
|
9.0 (12 Reviews)
1 Bedroom 2 Guests
10.0 (13 Reviews)
2 Bedrooms 6 Guests
10.0 (13 Reviews)
1 Bedroom 2 Guests
|
8.8 (42 Reviews)
13 Bedrooms 26 Guests
10.0 (12 Reviews)
3 Bedrooms 6 Guests
8.8 (7 Reviews)
3 Bedrooms 6 Guests
10.0 (10 Reviews)
1 Bedroom 3 Guests
8.7 (3 Reviews)
1 Bedroom 2 Guests
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8.3 (8 Reviews)
1 Bedroom 4 Guests
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8.3 (3 Reviews)
3 Bedrooms 6 Guests
10.0 (8 Reviews)
3 Bedrooms 6 Guests
10.0 (6 Reviews)
3 Bedrooms 6 Guests
9.8 (54 Reviews)
1 Bedroom 2 Guests
10.0 (2 Reviews)
2 Bedrooms 4 Guests
From US $331 per night
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6.8 (30 Reviews)
1 Bedroom 2 Guests
|
9.8 (43 Reviews)
1 Bedroom 2 Guests
5.5 (2 Reviews)
4 Bedrooms 6 Guests
9.8 (29 Reviews)
1 Bedroom 2 Guests
From US $9,931 per night
|
New
8 Bedrooms 16 Guests
From US $4,525 per night
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New
3 Bedrooms 6 Guests
10.0 (2 Reviews)
2 Bedrooms 4 Guests
From US $4,432 per night
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New
4 Bedrooms 10 Guests
10.0 (1 Review)
6 Bedrooms 12 Guests
From US $3,208 per night
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New
4 Bedrooms 8 Guests
10.0 (1 Review)
6 Bedrooms 12 Guests
|
New
5 Bedrooms 10 Guests
10.0 (1 Review)
4 Bedrooms 8 Guests
10.0 (1 Review)
5 Bedrooms 10 Guests

About Casai's Private Villas and Holiday Rentals in Windward

Discover more than 2348 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 842.83 ft², with nightly prices averaging US $3,646.

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.

Frequently Asked Questions About Windward?

What are the top holiday rentals in Windward?

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

As of 2025, Casai boasts over 2348 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.