Leeward Winter Rental
Villa
10.0(86 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
Private Pool
Oceanfront
Pool
Ocean View
£1,077/Night
7 Nights - £7,539
Villa
10.0(1 Review)
2 Bedrooms
3 Baths
4 Guests
1184.03 ft²
- Oceanfront
Hot Tub- Pool
- Ocean View
£1,396/Night
7 Nights - £9,772
Villa
10.0(69 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£347/Night
7 Nights - £2,432
House
9.8(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1506.95 ft²
- Oceanfront
- Hot Tub
- Ocean View
Balcony/Terrace
£912/Night
7 Nights - £6,381
House
10.0(52 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£452/Night
7 Nights - £3,167
Apartment
9.6(50 Reviews)
7 Bedrooms
1 Bath
4 Guests
753.47 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£695/Night
7 Nights - £4,863
Villa
10.0(25 Reviews)
2 Bedrooms
3 Baths
4 Guests
1938 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£550/Night
7 Nights - £3,853
Villa
9.6(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
968.75 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
£316/Night
7 Nights - £2,210
Villa
10.0(22 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,308/Night
7 Nights - £9,159
Villa
8.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
2152.78 ft²
- Oceanfront
- Hot Tub
Spa- Pool
£2,287/Night
7 Nights - £16,006
Villa
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
1800 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£482/Night
7 Nights - £3,377
House
5 Bedrooms
5 Baths
10 Guests
7211.82 ft²
- Private Pool
Private Beach- Oceanfront
- Hot Tub
£1,985/Night
7 Nights - £13,893
Why Choose Rent By Owner for your Leeward Winter Rental?
What makes our Winter Rental 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 Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. 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 Winter Rental Amenities
What amenities can you expect?
Our Winter Rental 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
La Grande Montagne
Frequently Asked Questions About Leeward Winter Rentals
1. What are the top Winter 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 Winter Rentals in Leeward:
- 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
- Harbor View 1
- Villa Arc En Ciel, Exotic Retreat On St. Barts
- ASIAN PEARL by WIMCO St. Barth Properties
- Villa Kuban | Ocean View - Located in Tropical Colombier with Private Pool
- Villa Kuban | Ocean View - Located in Stunning Colombier with Private Pool
- Villa Kuban | Ocean View - Located in Tropical Colombier with Private Pool
2. How many Winter Rentals are available in Leeward?
Currently, the total number of properties listed by RBO in 2026 is over 842 in the Leeward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Leeward.
More Rentals You May Like Near Leeward
Villa
10.0(11 Reviews)
1 Bedroom
1 Bath
2 Guests
861 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
£298/Night
7 Nights - £2,084
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
2476 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,514/Night
7 Nights - £10,598
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,393/Night
7 Nights - £9,753
Villa
10.0(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,054/Night
7 Nights - £7,379
Villa
10.0(7 Reviews)
4 Bedrooms
4 Baths
8 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£2,436/Night
7 Nights - £17,054
Apartment
10.0(7 Reviews)
1 Bedroom
1 Bath
3 Guests
538 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£317/Night
7 Nights - £2,216
Villa
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,054/Night
7 Nights - £7,379
Villa
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,054/Night
7 Nights - £7,379
Apartment
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
£678/Night
7 Nights - £4,744
House
10.0(5 Reviews)
3 Bedrooms
4 Baths
7 Guests
1500 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£979/Night
7 Nights - £6,854
Apartment
10.0(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1292 ft²
- Ocean View
- Balcony/Terrace
View
Pet Friendly
£571/Night
7 Nights - £3,996
Villa
10.0(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
861 ft²
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
£298/Night
7 Nights - £2,084
