Leeward Summer Rental
Villa
10.0(86 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
Private Pool
Oceanfront
Pool
Ocean View
£1,079/Night
7 Nights - £7,556
House
10.0(5 Reviews)
12 Bedrooms
13 Baths
28 Guests
322.92 ft²
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
£1,591/Night
7 Nights - £11,134
£2,315/Night
7 Nights - £16,205
Villa
10.0(69 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
Hot Tub- Pool
£348/Night
7 Nights - £2,437
Villa
10.0(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
1829.86 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£672/Night
7 Nights - £4,702
House
10.0(52 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
£452/Night
7 Nights - £3,165
Villa
10.0(1 Review)
2 Bedrooms
3 Baths
4 Guests
1184.03 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£1,399/Night
7 Nights - £9,793
Villa
10.0(30 Reviews)
3 Bedrooms
3 Baths
6 Guests
753 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£597/Night
7 Nights - £4,178
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1076.39 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£639/Night
7 Nights - £4,475
Villa
10.0(25 Reviews)
2 Bedrooms
3 Baths
4 Guests
1938 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£552/Night
7 Nights - £3,861
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
1076.39 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£526/Night
7 Nights - £3,684
Villa
10.0(22 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£1,616/Night
7 Nights - £11,310
Why Choose Rent By Owner for your Leeward Summer Rental?
What makes our Summer 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 Summer Rental
What's our booking process?
Our platform allows you to browse a curated selection of summer 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 Summer Rental Amenities
What amenities can you expect?
Our Summer 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 Luxury Rentals
1. What are the top Summer 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 Summer Rentals in Leeward:
- Villa Art | Ocean View - Located in Fabulous Flamands with Private Pool
- Villa Pain de Sucre - 4 Bedrooms - Flamands
- On the Beach, in Saint Barth. Villa Mellow Mood
- Beautiful 2-bedroom apartment in Gustavia with harbor view in Saint Barthélémy
- Ocean-view apartment in central Gustavia, St Barth; steps from the beach
- 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
2. How many Summer Rentals are available in Leeward?
Currently, the total number of properties listed by RBO in 2026 is over 2370 in the Leeward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Summer Rentals in Leeward.
More Rentals You May Like Near Leeward
House
10.0(1 Review)
1 Bedroom
2 Baths
4 Guests
1076.39 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
View
£371/Night
7 Nights - £2,598
Villa
10.0(22 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,311/Night
7 Nights - £9,179
Villa
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
1800 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£483/Night
7 Nights - £3,384
Villa
10.0(14 Reviews)
1 Bedroom
1 Bath
2 Guests
1345 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£500/Night
7 Nights - £3,500
Villa
10.0(11 Reviews)
1 Bedroom
1 Bath
2 Guests
861 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
£298/Night
7 Nights - £2,089
Villa
10.0(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
2476 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,486/Night
7 Nights - £10,399
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,396/Night
7 Nights - £9,774
Villa
10.0(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,056/Night
7 Nights - £7,395
Villa
10.0(9 Reviews)
1 Bedroom
1 Bath
2 Guests
646 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£543/Night
7 Nights - £3,798
Villa
10.0(7 Reviews)
4 Bedrooms
4 Baths
8 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£2,442/Night
7 Nights - £17,092
Apartment
10.0(7 Reviews)
1 Bedroom
1 Bath
3 Guests
538 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£317/Night
7 Nights - £2,215
Villa
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,056/Night
7 Nights - £7,395
