Leeward Resorts
Villa
10.0(86 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
Private Pool
Oceanfront
Pool
Ocean View
US $1,784/Night
7 Nights - US $12,489
House
10.0(5 Reviews)
12 Bedrooms
13 Baths
28 Guests
322.92 ft²
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
US $2,159/Night
7 Nights - US $15,113
US $1,614/Night
7 Nights - US $11,296
Villa
10.0(69 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
Hot Tub- Pool
US $369/Night
7 Nights - US $2,584
Villa
10.0(1 Review)
2 Bedrooms
3 Baths
4 Guests
1184.03 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $1,899/Night
7 Nights - US $13,293
House
10.0(52 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $680/Night
7 Nights - US $4,759
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1076.39 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $868/Night
7 Nights - US $6,075
Villa
10.0(30 Reviews)
3 Bedrooms
3 Baths
6 Guests
754 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $842/Night
7 Nights - US $5,891
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1076.39 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $714/Night
7 Nights - US $5,000
New
Villa
10.0(25 Reviews)
2 Bedrooms
3 Baths
4 Guests
1938 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $748/Night
7 Nights - US $5,239
House
10.0(1 Review)
1 Bedroom
2 Baths
4 Guests
1076.39 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
View
US $504/Night
7 Nights - US $3,527
Villa
10.0(22 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $2,466/Night
7 Nights - US $17,262
Why Choose Rent By Owner for your Leeward Resorts?
What makes our Resorts 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 Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. 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 Resorts Amenities
What amenities can you expect?
Our Resorts 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
Colombier
Terre Neuve
Saint-Jean
Anse des Lezards
Anse des Cayes
Public
La Grande Montagne
Leeward Resorts Frequently Asked Questions
1. What are the top Resorts 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 Resorts in Leeward:
- The Perfect View of Anse de Cayes/St Jean Beach
- VILLA ANGEL ROCK
- Villa Haute Maison - Hills of Colombier; RENTAL CAR INCL.: May 1 - Oct 31
- 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
- Maison 1 CH Entièrement Climatisé
- Blue Swan - Luxury 4 Bedroom Villa in Lurin St Barts
- Bianca 4-bedroom villa located in Corossol on the southwestern edge of St Barths
2. How many Resorts are available in Leeward?
Currently, the total number of properties listed by RBO in 2026 is over 2358 in the Leeward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Leeward.
More Rentals You May Like Near Leeward
Villa
9.8(17 Reviews)
2 Bedrooms
2 Baths
4 Guests
1614.59 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,004/Night
7 Nights - US $7,025
Villa
10.0(22 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,318/Night
7 Nights - US $9,226
Villa
10.0(11 Reviews)
1 Bedroom
1 Bath
2 Guests
861 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $450/Night
7 Nights - US $3,150
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
2476 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $4,369/Night
7 Nights - US $30,581
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $2,669/Night
7 Nights - US $18,684
Villa
10.0(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,584/Night
7 Nights - US $11,088
Villa
10.0(9 Reviews)
1 Bedroom
1 Bath
2 Guests
646 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $539/Night
7 Nights - US $3,776
Apartment
10.0(8 Reviews)
1 Bedroom
1 Bath
3 Guests
538 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $473/Night
7 Nights - US $3,313
Villa
10.0(7 Reviews)
4 Bedrooms
4 Baths
8 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $2,435/Night
7 Nights - US $17,047
Villa
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,603/Night
7 Nights - US $11,219
Villa
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,584/Night
7 Nights - US $11,088
Apartment
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $964/Night
7 Nights - US $6,748
