Windward Oceanfront Vacation Rentals
Cottage
10.0(98 Reviews)
1 Bedroom
1 Bath
2 Guests
Private Pool
Pool
Ocean View
Balcony/Terrace
CA $548/Night
7 Nights - CA $3,840
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
Oceanfront- Pool
- Ocean View
- Balcony/Terrace
CA $929/Night
7 Nights - CA $6,502
CA $3,131/Night
7 Nights - CA $21,918
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
10 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $4,789/Night
7 Nights - CA $33,521
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
CA $1,930/Night
7 Nights - CA $13,510
Villa
10.0(25 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $2,752/Night
7 Nights - CA $19,265
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $1,804/Night
7 Nights - CA $12,629
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Ocean View
- Balcony/Terrace
View
Kitchen
CA $320/Night
7 Nights - CA $2,241
House
9.6(8 Reviews)
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $261/Night
7 Nights - CA $1,826
Villa
10.0(20 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $554/Night
7 Nights - CA $3,881
Resort
9.5(2 Reviews)
31 Baths
75 Guests
850.89 ft²
Private Beach- Oceanfront
- Hot Tub
Spa
CA $1,858/Night
7 Nights - CA $13,007
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $4,789/Night
7 Nights - CA $33,521
Why Choose Rent By Owner for your Windward Oceanfront Vacation Rentals?
What makes our Oceanfront Vacation Rentals 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 Oceanfront Vacation Rentals
What's our booking process?
Our platform allows you to browse a curated selection of oceanfront vacation rentals. 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 Oceanfront Vacation Rentals Amenities
What amenities can you expect?
Our Oceanfront Vacation Rentals 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
Morne de Depoudre
Grand Cul de Sac
Frequently Asked Questions About Windward Oceanfront Rentals
1. What are the top Oceanfront Rentals 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 Oceanfront Rentals in Windward:
- Villa Angelique - Luxury 4 Bedroom Villa with Private Pool - St Barts
- Villa La Vue
- Villa La Magnifica | Ocean View - Located in Magnificent Deve with Private Pool
- Appartement St Jean, Saint-barthélemy
- Villa Paradise .
- 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 Case et Cuisine (2 bedrooms)
- Villa Avalon | Ocean View - Located in Exquisite Gouverneur with Private Pool
2. How many Oceanfront Rentals are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 2198 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Oceanfront Rentals in Windward.
More Rentals You May Like Near Windward
Villa
9.3(40 Reviews)
13 Bedrooms
13 Baths
26 Guests
1453.13 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $669/Night
7 Nights - CA $4,685
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
6 Guests
2153 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $4,789/Night
7 Nights - CA $33,521
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,294/Night
7 Nights - CA $9,056
Villa
10.0(12 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $3,373/Night
7 Nights - CA $23,614
Villa
10.0(11 Reviews)
4 Bedrooms
3 Baths
8 Guests
2150 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,966/Night
7 Nights - CA $13,761
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,706/Night
7 Nights - CA $11,940
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1712 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
CA $1,297/Night
7 Nights - CA $9,082
Villa
10.0(10 Reviews)
1 Bedroom
1 Bath
3 Guests
1 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
CA $1,201/Night
7 Nights - CA $8,410
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,156/Night
7 Nights - CA $8,088
Villa
10.0(6 Reviews)
3 Bedrooms
3 Baths
7 Guests
2153 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $2,522/Night
7 Nights - CA $17,654
Villa
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
CA $1,623/Night
7 Nights - CA $11,357
Villa
10.0(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
1615 ft²
- Private Pool
- Pool
- Ocean View
- View
CA $1,245/Night
7 Nights - CA $8,713
