Windward Oceanfront Vacation Rentals
Cottage
10.0(101 Reviews)
1 Bedroom
1 Bath
2 Guests
Private Pool
Parking
Pool
Ocean View
US $451/Night
7 Nights - US $3,155
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
Oceanfront- Parking
- Pool
- Ocean View
US $679/Night
7 Nights - US $4,750
US $2,287/Night
7 Nights - US $16,012
Villa
10.0(27 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
Hot Tub
Breakfast
US $1,748/Night
7 Nights - US $12,234
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $1,410/Night
7 Nights - US $9,870
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $3,083/Night
7 Nights - US $21,580
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
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
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(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $2,815/Night
7 Nights - US $19,707
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $857/Night
7 Nights - US $5,999
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
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 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:
- 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 .
- Villa Wings - Luxury 4 Bedroom Villa With Private Pool - Located in St Jean
- Villa Avalon | Ocean View - Located in Exquisite Gouverneur with Private Pool
- Villa Avalon | Ocean View - Located in Stunning Gouverneur with Private Pool
- Villa Avalon | Ocean View - Located in Fabulous Gouverneur with Private Pool
- Villa Avalon | Ocean View - Located in Wonderful Gouverneur with Private Pool
- VILLA LEO St jean St barthélemy
2. How many Oceanfront Rentals are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 2125 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
Resort
9.6(8 Reviews)
20 Baths
75 Guests
850.89 ft²
Private Beach- Oceanfront
- Hot Tub
- Breakfast
US $1,357/Night
7 Nights - US $9,502
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 $1,050/Night
7 Nights - US $7,348
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(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1712 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,126/Night
7 Nights - US $7,883
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,038/Night
7 Nights - US $7,263
Villa
10.0(10 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $975/Night
7 Nights - US $6,823
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $948/Night
7 Nights - US $6,639
Villa
10.0(8 Reviews)
3 Bedrooms
3 Baths
7 Guests
2153 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
US $1,989/Night
7 Nights - US $13,920
Villa
10.0(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $1,363/Night
7 Nights - US $9,538
Villa
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
1561 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,342/Night
7 Nights - US $9,393
Villa
10.0(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $767/Night
7 Nights - US $5,369
