A coastal town with colorful buildings, a marina with boats, and a mountainous backdrop.

Villas in Leeward

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Leeward villas

Outdoor pool, a heated pool

SUPERIOR WATERFRONT PRIVACY AVAILABLE SUMMER DATES NOW

SUPERIOR WATERFRONT PRIVACY AVAILABLE SUMMER DATES NOW
Anse des Lézards
10.0 out of 10, Exceptional, (69 reviews)
"Villa Alexi is an amazing home, spacious, beautiful, with an incredible location. The pool is wonderful, and the kitchen completely equipped with any utensil a professional chef would need. Byron is an outstanding host, very communicative. Olivia, the housekeeper, is excellent and very professional and friendly. An amazing value."
United States
Kent G.
SUPERIOR WATERFRONT PRIVACY AVAILABLE SUMMER DATES NOW
Outdoor pool

Villa Cinnamon sunset and sea view

Villa Cinnamon sunset and sea view
Public
10.0 out of 10, Exceptional, (2 reviews)
"A modern and clean villa that is very intuitive. The gated location is convenient for shopping, food, and exploration. Also quick communication with the the host if you need anything."
United States
Jami K.
Villa Cinnamon sunset and sea view
Outdoor dining

🏝REAL VILLA ON THE BEACH !SURFSPOT🏝CLOSE TO FLAMANS-STJEAN BEACH .REST.BARS

🏝REAL VILLA ON THE BEACH !SURFSPOT🏝CLOSE TO FLAMANS-STJEAN BEACH .REST.BARS
Anse des Cayes
10.0 out of 10, Exceptional, (86 reviews)
"A wonderful and romantic stay overlooking the turquoise ocean. The villa is very pleasant, even better than in the photos. The gazebo at sunset offered us a magnificent spectacle. Private beach access is very convenient; the right side of the beach is suitable for surfing, even for beginners, while the left side is for children. My son enjoyed the pool lights, whose colors can be changed. The proximity to town is a bonus. We will be back. Alexandra"
United States
Corinne B.
🏝REAL VILLA ON THE BEACH !SURFSPOT🏝CLOSE TO FLAMANS-STJEAN BEACH .REST.BARS
Outdoor pool, a heated pool

Luxury villa with magnificent sea view

Luxury villa with magnificent sea view
Anse des Lézards
10.0 out of 10, Exceptional, (30 reviews)
"We are just back from another wonderful stay in this lovely villa. It's a beautifully situated place, perched just above the sea, enveloped by ocean breezes. It's also impeccably kept up and well managed (thank you Clement) and was totally comfortable for six people. This is a really warm and special place to return to each year. "
United States
Patricia R.
Luxury villa with magnificent sea view
Outdoor pool, a heated pool

SUNSET VILLA ANGEL ****

SUNSET VILLA ANGEL ****
Colombier
10.0 out of 10, Exceptional, (14 reviews)
"Great spot for a romantic stay for two! Right next to Petite Colombe bakery and Bananiers, so close they’re walkable. 5 minute drive to Gustavia. Beautiful views! Definitely would book again! "
United States
Elizabeth G.
SUNSET VILLA ANGEL ****
A heated pool

Villa Privilege | Water View - Located in Tropical Gustavia with Private Pool

Villa Privilege | Water View - Located in Tropical Gustavia with Private Pool
Gustavia
Villa Privilege | Water View - Located in Tropical Gustavia with Private Pool
Outdoor dining

LUMIERE by WIMCO St. Barth Properties

LUMIERE by WIMCO St. Barth Properties
Merlette
LUMIERE by WIMCO St. Barth Properties
A heated pool

Villa Vue mer Panoramique, à 5 Minute de la Plage !

Villa Vue mer Panoramique, à 5 Minute de la Plage !
Anse des Cayes
9.8 out of 10, Exceptional, (10 reviews)
"The property has an amazing view and the staff was so friendly and helpful. Highly recommend!"
United States
Jackson H.
The price is AED 5,456
AED 8,116 total
includes taxes & fees
29 Jun - 30 Jun
Villa Vue mer Panoramique, à 5 Minute de la Plage !
Property grounds

Villa Rose des Cayes in Saint Barthelemy with parking and private pool

Villa Rose des Cayes in Saint Barthelemy with parking and private pool
Anse des Lézards
8.4 out of 10, Very Good, (5 reviews)
"The location was great, the villa spotless and well equipped. The garden is charming."
United States
Alice
Villa Rose des Cayes in Saint Barthelemy with parking and private pool
Outdoor pool, a heated pool

Villa Naos

Villa Naos
Anse des Cayes
Villa Naos
An infinity pool, a heated pool

Villa VOGUE - Panoramic Ocean View - St Jean

Villa VOGUE - Panoramic Ocean View - St Jean
Saint-Jean
10.0 out of 10, Exceptional, (22 reviews)
"Was amazing and the house was fully equipped and crowd amazing. We will be back!!!"
United States
Jack D.
Villa VOGUE - Panoramic Ocean View - St Jean
Terrace/patio

Located on the famous island of St. Barts, Villa Eugenie is a charming house.

Located on the famous island of St. Barts, Villa Eugenie is a charming house.
Anse des Cayes
10.0 out of 10, Exceptional, (5 reviews)
"Fabulous stay at a lovely villa with a great host, who made everything comfortable and seamless including assistance with a rental car and providing some great insights into the island. Would certainly stay again. "
United States
Vincent D.
Located on the famous island of St. Barts, Villa Eugenie is a charming house.
Terrace/patio

beautiful architect villa

beautiful architect villa
Anse des Lézards
9.6 out of 10, Exceptional, (24 reviews)
"Villa Pelican is beautiful and in an ideal location, close to the airport, supermarket and boulengerie. The villa is well appointed, the kitchen is very modern and functional, the living room is comfortable, the dining table comfortably seats 8 people, and the bedrooms are spacious and comfortable with king size beds. The only thing we would have liked is a door on the bathrooms for privacy. Even if you’re staying with a partner or spouse, it would be nice to have privacy when using the toilet....
United States
Adam H.
beautiful architect villa
Outdoor pool

🏝 BEACH VILLA CENTRAL LOCATION BETW ST JEAN 🏖 FLAMMANS BEACH 4 min TO CITY

🏝 BEACH VILLA CENTRAL LOCATION BETW ST JEAN 🏖 FLAMMANS BEACH 4 min TO CITY
Anse des Cayes
10.0 out of 10, Exceptional, (10 reviews)
"We had a wonderful stay at this beautiful place on the beach. Joce was very friendly and helpful - he even drove some of us to the airport when we couldn't fit all of our bags in the car. The place is so relaxing and beautiful, we had trouble leaving even to see other parts of the island."
United States
Todd G.
🏝 BEACH VILLA CENTRAL LOCATION BETW ST JEAN 🏖 FLAMMANS BEACH 4 min TO CITY
Outdoor pool, a heated pool

Villa KOSY - sunset & beach on foot

Villa KOSY - sunset & beach on foot
Public
Villa KOSY - sunset & beach on foot
Pool

Villa Asian Pearl | Hilltop Ocean & Island Views, Infinity Pool, Private Deck

Villa Asian Pearl | Hilltop Ocean & Island Views, Infinity Pool, Private Deck
Merlette
10.0 out of 10, Exceptional, (3 reviews)
"Amazing !! "
United States
Guillaume d.
Villa Asian Pearl | Hilltop Ocean & Island Views, Infinity Pool, Private Deck
Outdoor dining

Villa BELHARRA – Contemporary Luxury with Breathtaking Sea Views

Villa BELHARRA – Contemporary Luxury with Breathtaking Sea Views
Colombier
Villa BELHARRA – Contemporary Luxury with Breathtaking Sea Views
On the beach

Villa MICELA – Beachfront Escape with Pool in Flamands, St. Barths

Villa MICELA – Beachfront Escape with Pool in Flamands, St. Barths
Flamands
10.0 out of 10, Exceptional, (2 reviews)
"We spent a delightful, quiet week here. Highly recommend it. "
United States
Michael B.
Villa MICELA – Beachfront Escape with Pool in Flamands, St. Barths
Terrace/patio

Villa MATAJAGUI – Stunning Modern Hillside Retreat in Flamands, St. Barths

Villa MATAJAGUI – Stunning Modern Hillside Retreat in Flamands, St. Barths
Flamands
Villa MATAJAGUI – Stunning Modern Hillside Retreat in Flamands, St. Barths
Pool

Villa ELA – Beachfront Paradise for Groups in Flamands, St. Barths

Villa ELA – Beachfront Paradise for Groups in Flamands, St. Barths
Flamands
Villa ELA – Beachfront Paradise for Groups in Flamands, St. Barths
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Leeward Hotel Reviews

GYP SEA Saint Barth

GYP SEA Saint Barth

10/10 Excellent
"Beautiful "
Nyasha R. 3-night trip
Posted 7 days ago
GYP SEA Saint Barth