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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  St. Barthelemy
  4.  Leeward

Refine your search

Price per night

Amenity Filter

Rating

3301 Best Vacation Rentals with Pool in Leeward (Starting from $577)

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
Check Availability
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
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
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
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
Check Availability
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
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
Check Availability
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
Check Availability
Heavenly Villa in Gustavia with Private Pool
Heavenly Villa in Gustavia with Private Pool
Villa
Gustavia, Saint Barthélemy
0.7k from Leeward center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$1209
Average price / night
Check Availability
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
Check Availability
Villa Nagabaaja near Anse des Cayes - 230 m² with pool
Villa Nagabaaja near Anse des Cayes - 230 m² with pool
Villa
Anse des Cayes, Saint Barthélemy
0.7k from Leeward center

Security/Safety, Pool, Pet Friendly, Internet, Air Conditioner, Parking, Barbecue/Outdoor Cooking

2 Bedrooms4 Guests
New to Booking
$5552
Average price / night
Check Availability
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 Nagabaaja
Villa Nagabaaja
Villa
Saint Barthelemy, Saint Barthélemy
0.7k from Leeward center

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

4 Bedrooms12 Guests
9.3

Superb

12 reviews

$1783
Average price / night
Check Availability
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

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Leeward.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods

Stay Near Leeward's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Leeward Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 3301 verified vacation rentals with a pool in Leeward. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Leeward vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $577 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Leeward offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Leeward welcome pets. Currently, 20 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Leeward often include additional outdoor features such as Pool, View, and Ocean View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Leeward offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.