Leeward Cottage Rentals
Villa
10.0(86 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
Private Pool
Oceanfront
Pool
Ocean View
£1,164/Night
7 Nights - £8,145
House
10.0(5 Reviews)
12 Bedrooms
13 Baths
28 Guests
322.92 ft²
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
£1,611/Night
7 Nights - £11,278
£1,404/Night
7 Nights - £9,829
Villa
10.0(69 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
Hot Tub- Pool
£280/Night
7 Nights - £1,960
Villa
10.0(1 Review)
2 Bedrooms
3 Baths
4 Guests
1184.03 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£1,417/Night
7 Nights - £9,920
House
10.0(52 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£451/Night
7 Nights - £3,160
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1076.39 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£648/Night
7 Nights - £4,534
Villa
10.0(22 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£1,319/Night
7 Nights - £9,236
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1076.39 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£533/Night
7 Nights - £3,731
Villa
10.0(22 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,309/Night
7 Nights - £9,164
House
10.0(1 Review)
1 Bedroom
2 Baths
4 Guests
1076.39 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
View
£376/Night
7 Nights - £2,632
Villa
10.0(14 Reviews)
1 Bedroom
1 Bath
2 Guests
1345 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£503/Night
7 Nights - £3,520
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:
- 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
- Picturesque Villa W/Beautiful Sunset Views Directly Over Shell Beach & Gustavia
- Secluded and Romantic Villa Overlooking St. Jean Bay
- Maison 1 CH Entièrement Climatisé
2. How many Cottages are available in Leeward?
Currently, the total number of properties listed by RBO in 2026 is over 2362 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
£749/Night
7 Nights - £5,242
Villa
10.0(11 Reviews)
1 Bedroom
1 Bath
2 Guests
861 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
£337/Night
7 Nights - £2,358
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,781/Night
7 Nights - £12,469
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
2476 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,270/Night
7 Nights - £8,890
Villa
10.0(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,070/Night
7 Nights - £7,491
Villa
10.0(9 Reviews)
1 Bedroom
1 Bath
2 Guests
646 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£542/Night
7 Nights - £3,792
Apartment
10.0(8 Reviews)
1 Bedroom
1 Bath
3 Guests
538 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£316/Night
7 Nights - £2,212
Villa
10.0(7 Reviews)
4 Bedrooms
4 Baths
8 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£2,438/Night
7 Nights - £17,064
Villa
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,070/Night
7 Nights - £7,491
Villa
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,070/Night
7 Nights - £7,491
Apartment
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
£727/Night
7 Nights - £5,087
Apartment
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1292 ft²
- Ocean View
- Balcony/Terrace
- View
Pet Friendly
£565/Night
7 Nights - £3,951
