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

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2974 Best Vacation Rentals with Private Pool in Leeward (Starting from $866)

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 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
Check Availability
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 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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Villa Always
Villa Always
Villa
Leeward, St. Barthelemy
1.5k from Leeward center

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

3 Bedrooms6 Guests
New to Booking
$2316
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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Villa The One
Villa The One
Villa
Leeward, St. Barthelemy
1.5k from Leeward center

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

3 Bedrooms6 Guests
New to Booking
$2762
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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Villa Amancaya
Villa Amancaya
Villa
Leeward, St. Barthelemy
1.5k from Leeward center

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

1 Bedroom14 Guests
New to Booking
$9979
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 Noah
Villa Noah
House
Saint-Jean, Saint Barthélemy
1.6k from Leeward center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Beach, Jacuzzis

5 Bedrooms10 Guests
New to Booking
$2699
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
Check Availability
Mi Casita
Mi Casita
Villa
Leeward, St. Barthelemy
1.6k from Leeward center

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

1 Bedroom2 Guests
New to Booking
$866
Average price / night
Check Availability
Villa Imagine
Villa Imagine
Villa
Leeward, St. Barthelemy
4.9k from Leeward center

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

3 Bedrooms6 Guests
New to Booking
$4525
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
Check Availability
Black Pearl
Black Pearl
Villa
Leeward, St. Barthelemy
5.0k from Leeward center

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

4 Bedrooms8 Guests
New to Booking
$3208
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 Apiano
Villa Apiano
Villa
Leeward, St. Barthelemy
5.0k from Leeward center

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

4 Bedrooms8 Guests
New to Booking
$1564
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
VILLA ANGEL ROCK
VILLA ANGEL ROCK
Villa
Gustavia, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Balcony, Barbecue, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

5 reviews

$1074
Average price / night
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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
Beautiful Mirador Luxury villa
Beautiful Mirador Luxury villa
Villa
Gustavia, 97133, Saint Barthelemy
0.1k from Leeward center

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

4 Bedrooms8 Guests
New to Booking
$7335
Average price / night
Check Availability
Angel Rock (1/2 Rooms)
Angel Rock (1/2 Rooms)
Villa
Gustavia, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$1107
Average price / night
Check Availability
Angel Rock Luxury villa
Angel Rock Luxury villa
Villa
Gustavia, 97133, Saint Barthelemy
0.1k from Leeward center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$1107
Average price / night
Check Availability

Pro Tip:
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Leeward Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 2974 verified vacation rentals with a private pool in Leeward. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Leeward vary depending on the property size, location, and travel season. Rates typically start from around $866 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Leeward also welcome pets. Currently, 7 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Leeward often include additional features such as Pool, Private Pool, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Leeward include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.