Vacation Rentals in Leeward, St. Barthelemy: Compare 10+ Sites & Save

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3525 Best Vacation Rentals in Leeward (Starting from $496)

VILLA ANGEL ROCK
VILLA ANGEL ROCK
Villa
Saint Barthelemy, Saint Barthélemy
0.1k from Leeward center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms4 Guests
9.8

Exceptional

17 reviews

$1293
Average price / night
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Villa Angel Rock | Colombier, St-Barths
Villa Angel Rock | Colombier, St-Barths
Villa
Saint-Barthélemy, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Barbecue, Breakfast Available, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$1121
Average price / night
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Villa Angel Sunset
Villa Angel Sunset
Villa
Gustavia, Saint Barthélemy
0.2k from Leeward center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, 4-star, Lodgings, Vacation rentals

1 Bedroom2 Guests
9.6

Exceptional

26 reviews

$577
Average price / night
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Villa Sasha | Corossol, St-Barths
Villa Sasha | Corossol, St-Barths
Villa
Saint-Barthélemy, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Barbecue, Breakfast Available, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$2242
Average price / night
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1493 lodge de charme le Santa Maria
1493 lodge de charme le Santa Maria
House
St Barthelemy, Saint Barthélemy
0.2k from Leeward center

B&bs, Cheap, Accommodations, Pools, Parking, Guest houses, Homestays, Cabins, Lodgings

3 Bedrooms2 Guests
10.0

Exceptional

1 reviews

$723
Average price / night
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Villa Dzir | Colombier, St-Barths
Villa Dzir | Colombier, St-Barths
Villa
Saint-Barthélemy, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Barbecue, Breakfast Available, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
New to Booking
$2760
Average price / night
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1493 lodge de charme le NINA
1493 lodge de charme le NINA
House
St Barthelemy, Saint Barthélemy
0.2k from Leeward center

B&bs, Cheap, Accommodations, Pools, Parking, Guest houses, Homestays, Cabins, Lodgings

2 Bedrooms2 Guests
10.0

Exceptional

1 reviews

$605
Average price / night
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Ideal Villa with Architectural Gem
Ideal Villa with Architectural Gem
Villa
Colombier, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Balcony, Barbecue, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, Pool

3 Bedrooms6 Guests
New to Booking
$3855
Average price / night
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On the Beach , in Saint Barth. Mellow Mood Villa
On the Beach , in Saint Barth. Mellow Mood Villa
House
Saint Barthelemy, Saint Barthélemy
0.3k from Leeward center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$1240
Average price / night
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Villa Habitation Saint Louis by Fantasia Villas
Villa Habitation Saint Louis by Fantasia Villas
Villa
Corossol, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Barbecue, Internet, Kitchen, Living Area, No Smoking, Patio, Pool, TV

4 Bedrooms8 Guests
New to Booking
$2144
Average price / night
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Villa Ti Pop - Corossol
Villa Ti Pop - Corossol
House
Anse des Flamands, Saint Barthélemy
0.3k from Leeward center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$496
Average price / night
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Please Inquire Before Booking – Luxury Villa
Please Inquire Before Booking – Luxury Villa
Villa
Gustavia, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Balcony, Barbecue, Free Parking, Internet, Kitchen, Microwave, No Smoking, Patio

2 Bedrooms4 Guests
New to Booking
$2052
Average price / night
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Sunset 1 and Sea view on St Eustache
Sunset 1 and Sea view on St Eustache
Apartment
Saint Barthelemy, Saint Barthélemy
0.4k from Leeward center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay, Family

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$725
Average price / night
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Sunset 2 and sea view on St Eustache
Sunset 2 and sea view on St Eustache
Apartment
Saint Barthelemy, Saint Barthélemy
0.4k from Leeward center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Places to stay, Family, Self-catering

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$726
Average price / night
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Chef included by Fantasia Villas: Villa Dzir
Chef included by Fantasia Villas: Villa Dzir
Villa
Colombier, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Barbecue, Fitness Equipment, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$3337
Average price / night
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Ocean Five
Ocean Five
Villa
Leeward, St. Barthelemy
0.4k from Leeward center

Pool, Internet, Parking, Wheelchair Accessible, Private Pool, Air Conditioner, Child Friendly

5 Bedrooms10 Guests
New to Booking
$4013
Average price / night
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Villa Pleasure by Fanatasia Villas
Villa Pleasure by Fanatasia Villas
Villa
Public, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Barbecue, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio, Pool

3 Bedrooms6 Guests
New to Booking
$1210
Average price / night
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Rêve de Saint Barth - Vue Mer - Piscine Chauffée & Jacuzzi
Rêve de Saint Barth - Vue Mer - Piscine Chauffée & Jacuzzi
Apartment
Gustavia, Saint Barthélemy
0.5k from Leeward center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Hot tubs, Places to stay

7 Bedrooms6 Guests
9.6

Exceptional

61 reviews

$945
Average price / night
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Villa Roche Brune by Fantasia Villas
Villa Roche Brune by Fantasia Villas
Villa
Anse des Cayes, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Barbecue, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio, Pool

2 Bedrooms4 Guests
New to Booking
$982
Average price / night
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The Red Cloud Villa with Incredible Ocean View !
The Red Cloud Villa with Incredible Ocean View !
House
Saint Barthelemy, Saint Barthélemy
0.6k from Leeward center

Accommodations, Pools, Parking, Homestays, Lodgings, Vacation rentals, Places to stay, Accessible hotels, Beach rentals

12 Bedrooms28 Guests
10.0

Exceptional

3 reviews

$2159
Average price / night
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D'Zir (1/3 Rooms) Luxury villa
D'Zir (1/3 Rooms) Luxury villa
Villa
Colombier, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Balcony, Barbecue, Free Parking, Internet, Kitchen, Microwave, No Smoking, Pool

1 Bedroom2 Guests
New to Booking
$2255
Average price / night
Check Availability
Villa Davina - Dreamy escape, sea view in St Barth
Villa Davina - Dreamy escape, sea view in St Barth
Villa
Saint Barthelemy, Saint Barthélemy
0.7k from Leeward center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

2 Bedrooms4 Guests
9.8

Exceptional

6 reviews

$709
Average price / night
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D'Zir (2/3 Rooms) Luxury villa
D'Zir (2/3 Rooms) Luxury villa
Villa
Colombier, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Balcony, Barbecue, Free Parking, Internet, Kitchen, Microwave, No Smoking, Pool

2 Bedrooms4 Guests
New to Booking
$2255
Average price / night
Check Availability
Beautiful D'Zir Luxury villa
Beautiful D'Zir Luxury villa
Villa
Colombier, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Balcony, Barbecue, Free Parking, Internet, Kitchen, Microwave, No Smoking, Pool

3 Bedrooms6 Guests
New to Booking
$2766
Average price / night
Check Availability
Mirador (1/4 Rooms) Luxury villa
Mirador (1/4 Rooms) Luxury villa
Villa
Gustavia, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Free Parking, Internet, Kitchen, Microwave, No Smoking, Pool, TV

1 Bedroom2 Guests
New to Booking
$7254
Average price / night
Check Availability
Mirador (2/4 Rooms) Luxury villa
Mirador (2/4 Rooms) Luxury villa
Villa
Gustavia, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Free Parking, Internet, Kitchen, Microwave, No Smoking, Pool, TV

2 Bedrooms4 Guests
New to Booking
$7276
Average price / night
Check Availability
Mirador (3/4 Rooms) Luxury villa
Mirador (3/4 Rooms) Luxury villa
Villa
Gustavia, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Free Parking, Internet, Kitchen, Microwave, No Smoking, Pool, TV

3 Bedrooms6 Guests
New to Booking
$7311
Average price / night
Check Availability

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Frequently Asked Questions

You can explore 3525 verified vacation rentals in Leeward. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Leeward vary depending on the season, property size, and location. Rates typically start from around $496 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Leeward include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Leeward welcome pets. Currently, 17 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Leeward often include amenities such as Pool, Balcony/Terrace, and View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.