Leeward Cottage Rentals
1600 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
£1,084/Night
For 7 Nights £7,590
322.92 ft²
28 Guests
12 Bedrooms
13 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
£1,597/Night
For 7 Nights £11,180
£2,325/Night
For 7 Nights £16,272
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
£350/Night
For 7 Nights £2,447
£674/Night
For 7 Nights £4,721
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
£455/Night
For 7 Nights £3,187
1184.03 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
£1,405/Night
For 7 Nights £9,834
753 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
£560/Night
For 7 Nights £3,917
1076.39 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
£642/Night
For 7 Nights £4,494
1938 ft²
4 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
£610/Night
For 7 Nights £4,270
1076.39 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
£528/Night
For 7 Nights £3,699
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
£1,320/Night
For 7 Nights £9,242
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
Anse des Lezards
Terre Neuve
Colombier
Anse des Cayes
Public
Le Palidor
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
- Villa Pain de Sucre - 4 Bedrooms - Flamands
- Ocean-view apartment in central Gustavia, St Barth; steps from the beach
- 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
2. How many Cottages are available in Leeward?
Currently, the total number of properties listed by RBO in 2026 is over 2397 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
1076.39 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- Balcony/Terrace
£373/Night
For 7 Nights £2,609
6 Guests
3 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
£1,627/Night
For 7 Nights £11,389
1800 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
£485/Night
For 7 Nights £3,399
1345 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
£458/Night
For 7 Nights £3,206
861 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Oceanfront
- Hot Tub
- Ocean View
£300/Night
For 7 Nights £2,103
2476 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
£1,805/Night
For 7 Nights £12,633
1600 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
£1,427/Night
For 7 Nights £9,989
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
£1,061/Night
For 7 Nights £7,426
646 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
£915/Night
For 7 Nights £6,407
3229 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
£2,459/Night
For 7 Nights £17,211
538 ft²
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
£316/Night
For 7 Nights £2,211
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
£1,073/Night
For 7 Nights £7,510
