Windward Accommodations
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
Private Pool
Parking
Pool
Balcony/Terrace
US $610/Night
7 Nights - US $4,270
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
Oceanfront- Parking
- Pool
Ocean View
US $477/Night
7 Nights - US $3,337
Villa
10.0(1 Review)
1 Bedroom
1 Bath
Air Conditioner
Internet
Pet Friendly
Child Friendly
US $1,467/Night
7 Nights - US $10,266
Villa
10.0(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,262/Night
7 Nights - US $8,834
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
- Oceanfront
Hot Tub- Parking
- Ocean View
US $920/Night
7 Nights - US $6,440
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $919/Night
7 Nights - US $6,433
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
Breakfast- Parking
- Pool
US $1,318/Night
7 Nights - US $9,226
Villa
10.0(27 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
US $1,736/Night
7 Nights - US $12,151
Villa
10.0(1 Review)
4 Bedrooms
3 Baths
6 Guests
1722.23 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $943/Night
7 Nights - US $6,600
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $2,803/Night
7 Nights - US $19,620
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Parking
- Ocean View
- Balcony/Terrace
View
US $271/Night
7 Nights - US $1,897
Why Choose Rent By Owner for your Windward Accommodations?
What makes our Accommodations special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Windward
How to Book Your Windward Accommodations
What's our booking process?
Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windward
Common Accommodations Amenities
What amenities can you expect?
Our Accommodations are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Windward
Quartier Lorient
Morne Criquet
Pointe Milou
Grand Cul-de-Sac
Anse de Toiny
Barriere des Quatres Vents
Petit Cul-de-Sac
Gouverneur
Camaruche
Grand Cul de Sac
Anse du Grand Cul-de-Sac
Frequently Asked Questions about Windward Accommodations
1. What are the top Accommodations 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 Accommodations in Windward:
- Villa La Magnifica | Ocean View - Located in Beautiful Deve with Private Pool
- Villa Endeavour So private, breathtaking ocean views, direct from owner !
- Villa Yvantino beachfront (2 bedroom)
- Villa Caco (3 bedrooms)
- Villa La Vue
- Villa La Magnifica | Ocean View - Located in Magnificent Deve with Private Pool
- NEW, INTIMATE BUNGALOW WITH POOL
- Appartement St Jean, Saint-barthélemy
- Beach 2 minutes' walk, private deck, tranquility
- Villa Samsara | Ocean View - Located in Wonderful Pointe Milou with Private Pool
2. How many Accommodations are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 3562 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Windward.
More Rentals You May Like Near Windward
Villa
9.7(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
75.35 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $899/Night
7 Nights - US $6,290
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,172/Night
7 Nights - US $8,204
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $868/Night
7 Nights - US $6,073
House
10.0(15 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
US $245/Night
7 Nights - US $1,718
Villa
10.0(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
2150 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,578/Night
7 Nights - US $11,046
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,044/Night
7 Nights - US $7,306
Villa
10.0(12 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,096/Night
7 Nights - US $21,670
Villa
10.0(11 Reviews)
2 Bedrooms
3 Baths
4 Guests
2153 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $866/Night
7 Nights - US $6,063
Villa
10.0(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
1475 ft²
- Private Pool
- Parking
- Pool
- Kitchen
US $853/Night
7 Nights - US $5,968
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1712 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,277/Night
7 Nights - US $8,940
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,077/Night
7 Nights - US $7,541
Villa
10.0(10 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $969/Night
7 Nights - US $6,784
