Windward Villa
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
Private Pool
Parking
Pool
Balcony/Terrace
CA $876/Night
7 Nights - CA $6,131
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
Oceanfront
Hot Tub- Parking
Ocean View
CA $1,978/Night
7 Nights - CA $13,845
Villa
10.0(1 Review)
1 Bedroom
1 Bath
Air Conditioner
Internet
Pet Friendly
Child Friendly
CA $2,057/Night
7 Nights - CA $14,401
Villa
10.0(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $1,796/Night
7 Nights - CA $12,571
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
Breakfast- Parking
- Pool
CA $1,849/Night
7 Nights - CA $12,942
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $1,287/Night
7 Nights - CA $9,011
Villa
10.0(1 Review)
4 Bedrooms
3 Baths
6 Guests
1722.23 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,322/Night
7 Nights - CA $9,258
Villa
10.0(27 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
CA $2,452/Night
7 Nights - CA $17,161
Villa
9.7(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
75.35 ft²
- Parking
- Balcony/Terrace
View- Air Conditioner
CA $1,261/Night
7 Nights - CA $8,823
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
CA $4,325/Night
7 Nights - CA $30,271
Villa
9.3(40 Reviews)
13 Bedrooms
13 Baths
26 Guests
1453.13 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
CA $686/Night
7 Nights - CA $4,802
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,642/Night
7 Nights - CA $11,497
Why Choose Rent By Owner for your Windward Villa?
What makes our Villa 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 Villa
What's our booking process?
Our platform allows you to browse a curated selection of villa. 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 Villa Amenities
What amenities can you expect?
Our Villa 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
Anse de Toiny
Grand Cul-de-Sac
Barriere des Quatres Vents
Petit Cul-de-Sac
Camaruche
Gouverneur
Grand Cul de Sac
Anse du Grand Cul-de-Sac
Frequently Asked Questions About Windward Rental Villas
1. What are the top Villas 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 Villas in Windward:
- Villa 'Coco de Mer' Breathtaking views over St. Jean, Eden Rock & nearby Islands
- 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
- Beach 2 minutes' walk, private deck, tranquility
- Villa Samsara | Ocean View - Located in Wonderful Pointe Milou with Private Pool
- Villa Costa Nova | Ocean View - Located in Stunning Gouverneur with Private Pool
- Villa Paradise .
2. How many Villas are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 3085 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Windward.
More Rentals You May Like Near Windward
Villa
9.3(4 Reviews)
4 Bedrooms
3 Baths
8 Guests
3767.37 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,655/Night
7 Nights - CA $11,587
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
CA $3,949/Night
7 Nights - CA $27,644
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
CA $1,202/Night
7 Nights - CA $8,415
Villa
10.0(15 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,367/Night
7 Nights - CA $9,571
Villa
10.0(13 Reviews)
4 Bedrooms
3 Baths
8 Guests
2150 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $2,213/Night
7 Nights - CA $15,495
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,473/Night
7 Nights - CA $10,307
Villa
10.0(12 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $4,343/Night
7 Nights - CA $30,398
Villa
10.0(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
1475 ft²
- Private Pool
- Parking
- Pool
Kitchen
CA $1,196/Night
7 Nights - CA $8,372
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1712 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,580/Night
7 Nights - CA $11,058
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,456/Night
7 Nights - CA $10,188
Villa
10.0(10 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,367/Night
7 Nights - CA $9,571
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
CA $1,330/Night
7 Nights - CA $9,313
