Leeward Cottage Rentals
Villa
10.0(86 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
Private Pool
Oceanfront
Pool
Ocean View
CA $2,188/Night
7 Nights - CA $15,315
House
10.0(5 Reviews)
12 Bedrooms
13 Baths
28 Guests
322.92 ft²
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
CA $3,029/Night
7 Nights - CA $21,205
CA $2,640/Night
7 Nights - CA $18,481
Villa
10.0(69 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
Hot Tub- Pool
CA $516/Night
7 Nights - CA $3,610
Villa
10.0(1 Review)
2 Bedrooms
3 Baths
4 Guests
1184.03 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
CA $2,665/Night
7 Nights - CA $18,652
House
10.0(52 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
CA $849/Night
7 Nights - CA $5,941
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1076.39 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $1,218/Night
7 Nights - CA $8,524
Villa
10.0(30 Reviews)
3 Bedrooms
3 Baths
6 Guests
753 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $1,052/Night
7 Nights - CA $7,368
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1076.39 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $1,002/Night
7 Nights - CA $7,016
Villa
10.0(25 Reviews)
2 Bedrooms
3 Baths
4 Guests
1938 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,035/Night
7 Nights - CA $7,249
House
10.0(1 Review)
1 Bedroom
2 Baths
4 Guests
1076.39 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
View
CA $707/Night
7 Nights - CA $4,949
Villa
10.0(22 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $2,481/Night
7 Nights - CA $17,365
Why Choose Rent By Owner for your Leeward Cottage Rentals?
What makes our Cottage 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 Cottage Rentals
What's our booking process?
Our platform allows you to browse a curated selection of cottage 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 Cottage Rentals Amenities
What amenities can you expect?
Our Cottage 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
Terre Neuve
Anse des Lezards
Colombier
Anse des Cayes
Public
La Grande Montagne
Frequently Asked Questions About Leeward Rental Cottages
1. What are the top Cottages 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 Cottages in Leeward:
- Villa Art | Ocean View - Located in Fabulous Flamands with Private Pool
- On the Beach, in Saint Barth. Villa Mellow Mood
- Beautiful 2-bedroom apartment in Gustavia with harbor view in Saint Barthélémy
- VILLA ANGEL ROCK
- The Perfect View of Anse de Cayes/St Jean Beach
- 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
2. How many Cottages are available in Leeward?
Currently, the total number of properties listed by RBO in 2026 is over 2363 in the Leeward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages 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
CA $1,408/Night
7 Nights - CA $9,857
Villa
10.0(22 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $2,461/Night
7 Nights - CA $17,230
Villa
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
1800 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $921/Night
7 Nights - CA $6,446
Villa
10.0(14 Reviews)
1 Bedroom
1 Bath
2 Guests
1345 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
CA $945/Night
7 Nights - CA $6,619
Villa
10.0(11 Reviews)
1 Bedroom
1 Bath
2 Guests
861 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
CA $560/Night
7 Nights - CA $3,922
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $3,349/Night
7 Nights - CA $23,445
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
2476 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $2,388/Night
7 Nights - CA $16,715
Villa
10.0(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $2,012/Night
7 Nights - CA $14,085
Villa
10.0(9 Reviews)
1 Bedroom
1 Bath
2 Guests
646 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,019/Night
7 Nights - CA $7,129
Apartment
10.0(8 Reviews)
1 Bedroom
1 Bath
3 Guests
538 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $594/Night
7 Nights - CA $4,159
Villa
10.0(7 Reviews)
4 Bedrooms
4 Baths
8 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $4,583/Night
7 Nights - CA $32,084
Villa
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $2,012/Night
7 Nights - CA $14,085
