Leeward Oceanfront Vacation Rentals
1600 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $2,006/Night
For 7 Nights CA $14,041
322.92 ft²
28 Guests
12 Bedrooms
13 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
CA $2,955/Night
For 7 Nights CA $20,682
CA $1,126/Night
For 7 Nights CA $7,885
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
CA $647/Night
For 7 Nights CA $4,527
CA $1,248/Night
For 7 Nights CA $8,734
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
CA $842/Night
For 7 Nights CA $5,895
1184.03 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
CA $2,599/Night
For 7 Nights CA $18,191
753 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $1,044/Night
For 7 Nights CA $7,310
1076.39 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
CA $1,188/Night
For 7 Nights CA $8,313
1938 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $1,129/Night
For 7 Nights CA $7,899
1076.39 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
CA $977/Night
For 7 Nights CA $6,842
6 Guests
3 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $3,009/Night
For 7 Nights CA $21,065
Why Choose Rent By Owner for your Leeward 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 Leeward
How to Book Your Leeward 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 Leeward
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 Leeward
Gustavia
Grande Vigie
Flamands Beach
Anse des Flamands
Saint-Jean
Anse des Lezards
Terre Neuve
Colombier
Anse des Cayes
Public
Le Palidor
Frequently Asked Questions About Leeward Oceanfront Rentals
1. What are the top Oceanfront Rentals in Leeward?
There are a lot of options in Leeward. If you plan on staying in the Leeward area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Oceanfront Rentals in Leeward:
- Villa Art | Ocean View - Located in Fabulous Flamands with Private Pool
- On the Beach, in Saint Barth. Villa Mellow Mood
- The Perfect View of Anse de Cayes/St Jean Beach
- VILLA ANGEL ROCK
- Beautiful 2-bedroom apartment in Gustavia with harbor view in Saint Barthélémy
- Located on the famous island of St. Barts, Villa Eugenie is a charming house.
- Villa Micela - Two Bedroom Beachfront Villa With Pool - St Barts Flamands Beach
- Villa Magic Bird | Ocean View - Located in Exquisite Flamands with Private Pool
- Villa Magic Bird | Ocean View - Located in Tropical Flamands with Private Pool
- Picturesque Villa W/Beautiful Sunset Views Directly Over Shell Beach & Gustavia
2. How many Oceanfront Rentals are available in Leeward?
Currently, the total number of properties listed by RBO in 2026 is over 1412 in the Leeward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Oceanfront Rentals in Leeward.
More Rentals You May Like Near Leeward
1076.39 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $690/Night
For 7 Nights CA $4,827
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $2,442/Night
For 7 Nights CA $17,096
1800 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $898/Night
For 7 Nights CA $6,287
1345 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $840/Night
For 7 Nights CA $5,879
861 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Oceanfront
- Hot Tub
- Ocean View
CA $556/Night
For 7 Nights CA $3,891
2476 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $2,818/Night
For 7 Nights CA $19,729
1600 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $2,640/Night
For 7 Nights CA $18,477
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $1,962/Night
For 7 Nights CA $13,737
646 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $1,693/Night
For 7 Nights CA $11,852
3229 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $4,548/Night
For 7 Nights CA $31,838
538 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
CA $590/Night
For 7 Nights CA $4,126
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $1,962/Night
For 7 Nights CA $13,737
