Windward Accommodations
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
Private Pool
Pool
Balcony/Terrace
Kitchen
R10,019/Night
7 Nights - R70,124
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
Oceanfront- Pool
Ocean View- Balcony/Terrace
R11,239/Night
7 Nights - R78,670
Villa
10.0(1 Review)
1 Bedroom
1 Bath
Pet Friendly
Air Conditioner
Internet
Child Friendly
R24,290/Night
7 Nights - R170,026
Villa
10.0(39 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
R6,956/Night
7 Nights - R48,692
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
R23,352/Night
7 Nights - R163,467
Villa
10.0(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
R19,261/Night
7 Nights - R134,831
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R21,828/Night
7 Nights - R152,801
Villa
10.0(32 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
R12,808/Night
7 Nights - R89,650
Villa
10.0(1 Review)
4 Bedrooms
3 Baths
6 Guests
1722.23 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R15,615/Night
7 Nights - R109,309
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
R13,585/Night
7 Nights - R95,099
Villa
10.0(26 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
R33,211/Night
7 Nights - R232,481
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
Barriere des Quatres Vents
Anse de Toiny
Petit Cul-de-Sac
Camaruche
Gouverneur
Morne de Depoudre
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:
- THE VILLA AFRICAN QUEEN - AN OASIS IN THE CARIBBEANS WITH A GIANT POOL !
- Villa Jelo - 3 bdr - 2.5 bth - Pool & SPA - Games Room
- Modern Villa Suite Acajous Boasts Splendid Views !
- Villa 'Coco de Mer' Breathtaking views over St. Jean, Eden Rock & nearby Islands
- 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)
- Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view
- Villa Caco (3 bedrooms)
- Villa Angelique - Luxury 4 Bedroom Villa with Private Pool - St Barts
2. How many Accommodations are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 3571 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
- Balcony/Terrace
View
Parking- Air Conditioner
R14,883/Night
7 Nights - R104,175
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R57,106/Night
7 Nights - R399,741
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
R3,873/Night
7 Nights - R27,112
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
R17,558/Night
7 Nights - R122,907
Villa
10.0(20 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R6,691/Night
7 Nights - R46,837
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R57,785/Night
7 Nights - R404,494
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R57,106/Night
7 Nights - R399,741
Villa
10.0(15 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
R14,497/Night
7 Nights - R101,476
House
10.0(15 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
R4,095/Night
7 Nights - R28,669
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R15,612/Night
7 Nights - R109,276
Villa
10.0(12 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R56,130/Night
7 Nights - R392,901
Villa
10.0(12 Reviews)
4 Bedrooms
3 Baths
8 Guests
2150 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R23,722/Night
7 Nights - R166,051
