50 Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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Leeward
1,267 properties
St. Jean
313 properties
Pointe Milou
266 properties
Gustavia
260 properties
Marigot
257 properties
Anse des Flamands
207 properties
Lurin
189 properties
Anse de Lorient
177 properties
Petit Cul de Sac
169 properties
Anse des Cayes
153 properties
Gouverneur
90 properties
Toiny
74 properties
Grand Cul-de-Sac
73 properties
Grand Fond
72 properties
Corossol
28 properties
Colombier
26 properties
Salines
22 properties

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1,266 Vacation rentals

12

Apartment rental in Anse des Cayes

St. Barts / Anse des Cayes

1 2 14 nights min

  • 1 bedroom
  • sleeps 2
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Apartment located in a small quiet, in the heights of Anse des Cayes, halfway between Gustavia and Saint John. This comfortable apartment in the decoration consists of a large living room, a small kitchen, bathroom with shower and a very nice terrace with sea view. En …see more

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from $207 / night

$1,446 / week

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from $207 / night

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20

Vacation villa with swimming pool in Gustavia

St. Barts / Gustavia

3 6 6 nights min

  • 3 bedrooms
  • sleeps 6
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated 350 meters from the St Jean Bay, one of the most beautiful beaches on the island. Located in the heart of a tropical garden which is guaranteed to give you the privacy and intimacy you desire. Within a short distance to some of the islands stores and restauran …see more

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from $559 / night

$3,912 / week

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from $559 / night

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24

Vacation villa with swimming pool in Anse des Flamands

Anse des Flamands / Flamands Beach

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Welcome to Villa Micela, a gorgeous two bedroom beach front villa in St Barths located directly on Flamands Beach. Wake up to the wonderful sea breezes. Bask in near perfect weather literally steps from one of the nicest beaches in St Barths. Flamands Beach is on …see more

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from $1,071 / night

$7,500 - $22,000 / week

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from $1,071 / night

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12

Villa rental in Gustavia with shared pool

St. Barts / Gustavia

1 2 6 nights min

  • 1 bedroom
  • sleeps 2
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Offering beautiful ocean views, the villa Fish is quiet, without vis-à-vis, located at the end of Colombier. This charming villa has a large kitchen open to the dining room, a cozy living room, a bedroom with bathroom. It also has a large covered terrace, a swimming poo …see more

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from $354 / night

$2,478 / week

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from $354 / night

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(2) Excellent 

6

St. Jean Vacation cottage rental

St. Barts / St. Jean

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
The CINDY Charming Cottage is located on the heights of Marigot, with sea views, quiet. Charming Cottage for 2 people, with a large terrace in Deck suite, Quality of Services, Non-Smoking, comfortable, air conditioned, King size bed, bathroom with double sinks, walk-in …see more

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from $796 / night

$5,570 / week

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avg. 3 hours 26 minutes

from $796 / night

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39

Vacation villa with shared pool in Gustavia

St. Barts / Gustavia

3 4 min stay varies

  • 3 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Quiet and relaxing, Villa Evan seduce you with its atmosphere that mixes the colors of the Caribbean with the sweetness and serenity of the country of the rising sun. Ideal for families, it has a beautiful swimming pool and a large garden. The villa is within 15 minutes …see more

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from $433 / night

$2,380 / week

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from $433 / night

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24

Vacation villa rental

St. Barts / Gustavia

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Villa Wings, a luxury 4 bedroom villa in St Barts. This contemporary and new built villa is located in the St-Jean Hillside with breath-taking panoramic views over St Jean Bay. The location of this villa is simple fantastic as you are within a few minutes fro …see more

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from $2,857 / night

$20,000 - $70,000 / week

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from $2,857 / night

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(2) Excellent 

7

Vacation villa in Colombier

St. Barts / Colombier

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Ask about children
  • Air conditioning
  • Private garden
We promise you are very unique holiday. The villa is very secluded. The views and sunsets are "Huge" Large terrace, edgeless pool and 5 person Heated Spa. Comfortable loungers and hammocks with a large living room and open plan luxury kitchen. Two fully air-conditioned …see more

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from $641 / night

$4,486 / week

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avg. 31 minutes

from $641 / night

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(5) Excellent 

23

Vacation cottage with swimming pool in St. Jean

St. Barts / St. Jean

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Air conditioning
Le Cottage de Charme LAGOON est situé sur les hauteurs de Marigot, avec une vue sur la mer, au calme. Cottage de Charme pour 2 personnes : Prestation de qualité, Non Fumeur, Chambre tout confort, climatisée, Lit king size, salle de bain, avec double vasques, douche Ital …see more

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from $792 / night

$5,544 / week

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avg. 3 hours 26 minutes

from $792 / night

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20

Gustavia Vacation villa rental

St. Barts / Gustavia

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Offering beautiful ocean views, the villa Fish is quiet, without vis-à-vis, located at the end of Colombier. This charming villa has a large kitchen open to the dining room, a comfortable living room, two bedrooms with two bathrooms. It also has a large covered terrace, …see more

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from $428 / night

$2,995 / week

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from $428 / night

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(1) Excellent 

24

Vacation villa with swimming pool in Gustavia

St. Barts / Gustavia

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Welcome to Villa Ted, a luxury 2 bedroom villa located in the beautiful surroundings of Dévé in St Barths. The villa offers guests a beautiful outdoor terrace area with ample space and provides stunning panoramic view of the over Grand Cul de Sac and the island of Tortu …see more

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from $723 / night

$5,060 - $17,000 / week

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from $723 / night

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“Picture Postcard View”

Reviewed 9 Jul 2017

We had the most amazing trip to St Barths again and this was the first time on vacation my husband had to drag me out of the villa every day. I just wanted to sit on the terrace looking out at the vie… More

Thank so much for your wonderful review. We are delighted to hear you enjoyed your trip to St Barths. Thanks once again for booking with us & we hope to have the opportunity to welcome you back again in the future. Warm regards, Linda

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15

Gustavia Vacation apartment rental

St. Barts / Gustavia

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Bel appartement sur le port de Gustavia offrant une vue imprenable sur les plus beaux yachts. Sa terrasse couverte vous offre une véritable sensation nautique, comme si vous diniez à bord d'un somptueux bateau. L'appartement se compose de trois niveaux : une chambre au …see more

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from $590 / night

$4,130 / week

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from $590 / night

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(1) Excellent 

26

Vacation villa with swimming pool in St. Jean

St. Barts / St. Jean

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Welcome to Villa Diamond, one of the most exquisite villa rental in St Jean, St Barth. The newly built villa boasts a stunningly beautiful and stylish design with breath-taking views. The villa is centrally located on the St Jean hillside overlooking St. Jean Bay with a …see more

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from $1,071 / night

$7,500 - $25,000 / week

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from $1,071 / night

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“We Enjoyed our Special Stay on the Island”

Reviewed 29 Jun 2017

We are just back from a wonderful trip at this villa. It was a special occasion for our 1st wedding anniversary and we have the most amazing time. The concierge was tremendous and made our trip one to… More

Hi Emma, Thank you so much for your wonderful review. I am delighted you had such a great wedding anniversary celebration. Warm regards, Exceptional Villas

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(1) Excellent 

24

Vacation villa with swimming pool in St. Jean

St. Barts / St. Jean

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Villa Isabella, a lovely 4 bedroom villa rental with private pool and breathtaking panoramic views located on the hillside over looking Saint Jean Bay. The lovely town of St Jean is less then half a kilometre from Villa Isabella. Saint Jean is second …see more

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from $2,286 / night

$16,000 - $22,000 / week

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from $2,286 / night

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“Loved This Location”

Reviewed 25 Apr 2017

My friends and I are just back home after a wonderful 5 days at villa Isabella. It was amazing- we loved the view, the villa and most importantly the location. It is located at the top of the hill in … More

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24

Vacation home with swimming pool in Colombier

St. Barts / Colombier

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Villa very nice to live where you feel good, with a nice view over the sea between green hills. It consists of a living room, a living room, 2 bedrooms with a bathroom (shower) for each: one bedroom with a king size bed (200 CM) a smaller room but equally comfortable wi …see more

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from $308 / night

$1,935 - $5,407 / week

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from $308 / night

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24

Vacation villa rental

St. Barts / St. Jean

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Welcome to Villa Ellena, a stunning and truly magical St Barths Villa rental. This luxury 3 bedroom villa is located midway between St. Jean and the village of Lorient and offers panoramic views over the turquoise St Jean Bay. Designed by an owner/architect wit …see more

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from $1,715 / night

$12,000 - $35,000 / week

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from $1,715 / night

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(1) Excellent 

23

Vacation villa with swimming pool in Colombier

St. Barts / Colombier

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Villa recent contemporary construction, decorated with taste and modern equipment, a fully equipped room, living room, kitchen. A place quiet and relaxing, large Terrace with pool, ocean views. Gustavia close to the airport, bakery etc. Concierge on request, possibili …see more

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from $442 / night

$3,967 / week

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Responds fast!
avg. 1 hour 40 minutes

from $442 / night

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(5) Excellent 

12

Vacation villa with swimming pool in Colombier

St. Barts / Colombier

2 2 5 nights min

  • 2 bedrooms
  • sleeps 2
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
We promise you are very unique holiday. The villa is very secluded and yet you are only a few minutes from everything. The views and sunsets from the villa are "Huge". Even the locals who have never been here say "Wow". Large terrace, an edgeless pool, a 5 person Heated …see more

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from $552 / night

$3,865 / week

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Responds fast!
avg. 31 minutes

from $552 / night

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(5) Excellent 

5

Vacation b&b with swimming pool in Anse des Cayes

St. Barts / Anse des Cayes

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
soyez les bienvenus dans nos chambres d'hôtes sur l'ile de St-Barthélémy. Petite Ile de 25km² avec ses 22 plages diverses et variées, de sable blanc en passant par les coquillages. Riche en culture grâce à des évènements mensuels ( course de bateau en Mars/Avril, even …see more

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from $170 / night

$952 / week

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Responds fast!
avg. 2 hours 49 minutes

from $170 / night

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(1) Excellent 

23

Vacation villa rental

St. Barts / Colombier

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Villa Belle Bague, one of the most luxurious 4 bedroom villa rental located high on the hillside in Colombier in St. Barts. With its high cliffs and long white beaches, and breath taking views, St. Barts is one of the Caribbean's most enticing island …see more

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from $2,571 / night

$18,000 - $55,000 / week

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from $2,571 / night

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“Great Villa for our Vacation”

Reviewed 28 Aug 2017

We had a great time at this villa. It was really nice and the views are amazing. We spent a lot of our time going to the beach and checking out recommended restaurants (thank you by the way) we had su… More

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13

Vacation villa with shared pool in Gustavia

St. Barts / Gustavia

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Tiwa is an amazing two-bedroom, two-bathroom villa located on the hillside of Pointe Milou. It offers incredible views, large bedrooms, fantastic interior. The gentle breezes of Pointe Milou keep the wondeful space cool and relaxing. Villa Tiwa is an amazing place. Nex …see more

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from $432 / night

$3,023 / week

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from $432 / night

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15

Vacation villa with swimming pool in St. Jean

St. Barts / St. Jean

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Welcome to Villa Zen, a luxury two bedroom villa set amid a tropical garden with wonderful sea views. The villa is located in the exclusive Pointe Milou area of St Barthsng> . The villa is very romantic and provides guests with plenty or outdoor space in matured grounds …see more

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from $1,000 / night

$7,000 - $16,500 / week

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from $1,000 / night

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4

Vacation villa with swimming pool in Gustavia

St. Barts / Gustavia

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Shell Beach Villa is a brand new mansion on the heights of Gustavia with stunning harbor views. It has a bedroom, a bathroom, a kitchen open to a living room, a covered terrace and a pool. Its modern décor mingling with the charm of natural materials provides a feeling …see more

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from $856 / night

$5,992 / week

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from $856 / night

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13

Vacation villa in Gustavia

St. Barts / Gustavia

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Child friendly
  • Ask about pets
Composée de deux chambres, une piscine et un jacuzzi, la villa Les Lézards offre une vue imprenable sur l'océan. Confortable et privative la villa est idéale pour un séjour entre amis ou en famille. Sa proximité avec le centre ville permet d'accéder en quelques minut …see more

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from $811 / night

$5,679 / week

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from $811 / night

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(1) Excellent 

10

St. Jean Vacation cottage rental

St. Barts / St. Jean

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
The Charming Cottage STEVE with its private pool is located on the heights of Marigot, with a beautiful sea calm. Charming Cottage for 2: Quality of Services, Non-Smoking, comfortable, air conditioned, King size bed, bathroom with double sinks, Italian, hairdryer shower …see more

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from $951 / night

$6,657 / week

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Responds fast!
avg. 3 hours 26 minutes

from $951 / night

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35

Vacation villa with shared pool in Gustavia

St. Barts / Gustavia

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Walhalla is a highly favored and private villa located on the hillside of Pointe Milou. It offers a simply stunning ocean view from all the rooms. Guests enjoy the spacious white villa with a pool, its complete privacy and the size of the estate. Walhalla is a spaciou …see more

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from $704 / night

$4,925 / week

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from $704 / night

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10

Vacation apartment in Gustavia

St. Barts / Gustavia

1 2 6 nights min

  • 1 bedroom
  • sleeps 2
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Bel appartement sur le port de Gustavia offrant une vue imprenable sur les plus beaux yachts. Sa terrasse couverte vous offre une véritable sensation nautique, comme si vous diniez à bord d'un somptueux bateau. L'appartement se compose d'une chambre avec sa salle de bai …see more

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from $516 / night

$3,614 / week

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from $516 / night

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10

Colombier Vacation villa rental

St. Barts / Colombier

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Tak is a wonderful very private villa on the hillside of Colombier, located at the end of a private road. This spacious, bright, peaceful and naturally breezed three bedroom, 2 bathroom villa offers beautiful views on the ocean and Gustavia harbour in the distance …see more

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from $791 / night

$5,532 / week

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from $791 / night

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19

Vacation villa in Anse des Cayes

St. Barts / Anse des Cayes

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Eranos is a modern villa with a neat design, designed by a talented architect on the ground floor you have two very large bedrooms and their adjoining bathroom which gives access to a large sunny deck and a pool of 11 meters heated between the two rooms a gym equi …see more

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from $878 / night

$6,142 - $8,774 / week

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from $878 / night

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15

Home rental in Anse des Flamands with swimming pool

St. Barts / Anse des Flamands

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
For an unforgettable holiday in St Barts, Angel Home is a villa that will charm you. Angel Home is a modern villa, refined and warm. Located on the Flemish hills, the villa offers a spectacular view of the Bay of Flemings. It comes with 2 sea view rooms with private bat …see more

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from $777 / night

$5,441 - $7,821 / week

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from $777 / night

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8

Vacation cottage rental

St. Barts / St. Jean

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
The Charming Cottage ALIZE is located on the heights of Marigot, with beautiful sea view and pool, quiet. Charming Cottage for 2: Quality of Services, Non-Smoking, comfortable, air conditioned, King size bed, bathroom with double sinks, Italian, hairdryer shower, safe, …see more

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from $785 / night

$5,490 / week

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Responds fast!
avg. 3 hours 26 minutes

from $785 / night

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23

Vacation villa rental

St. Barts / Gustavia

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa New Coast enjoys an extraordinary view of the ocean and the surrounding nature. Located close to Gouverneur Beach, the villa offers a little piece of paradise in peace. You can enjoy the beautiful view of the sunset while enjoying a cocktail in the jacuzzi. Co …see more

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from $656 / night

$4,595 / week

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from $656 / night

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16

Villa accommodation in Gustavia with shared pool

St. Barts / Gustavia

1 2 6 nights min

  • 1 bedroom
  • sleeps 2
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Greek villa, ideally located on the heights of Colombier, offers extraordinary ocean views. Dominant entirely Flemish sea and bay, swimming pool overlooks the ocean. The bedroom has a private lounge. tranquility lovers will be delighted by the privacy and quiet of t …see more

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from $568 / night

$3,976 / week

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from $568 / night

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24

Vacation villa rental

St. Barts / Lurin

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Acamar, one of the most stunning 3 bedroom villas with private pool and incredible sea views located over looking Toiny Beach. As you enter this exceptional villa, the view to the exquisitely furnished sitting room, sun terrace, lovely heated swimming pool an …see more

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from $1,786 / night

$12,500 - $40,000 / week

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from $1,786 / night

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5

Vacation b&b in Anse des Cayes

St. Barts / Anse des Cayes

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
welcome to our guest rooms on the island of St Barts. Small island of 25km² with 22 diverse and varied beaches, white sand through the shells. Rich in culture through monthly events (boat race in March / April, musical events, the festival theater and cinema). A set of …see more

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from $170 / night

$952 / week

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Responds fast!
avg. 2 hours 49 minutes

from $170 / night

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21

Villa rental in Colombier with swimming pool

St. Barts / Colombier

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Air conditioning
In addition to boasting a great hilltop location and close-to-town convenience, Villa LENALEE is a four-bedroom home is the ideal choice for newcomers just getting to know St. Barts. Situated above Flamands Bay, Villa LENALEE looks out over the green of the surroundin …see more

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from $1,009 / night

$7,058 - $39,271 / week

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from $1,009 / night

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12

Gustavia Vacation villa rental

St. Barts / Gustavia

1 2 6 nights min

  • 1 bedroom
  • sleeps 2
  • 6 nights min
  • Child friendly
  • Ask about pets
Composée d'une chambre, une piscine et un jacuzzi, la villa Les Lézards offre une vue imprenable sur l'océan. Confortable et privative la villa est idéale pour un séjour de détente. Sa proximité avec le centre ville permet d'accéder en quelques minutes aux restaurants …see more

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from $664 / night

$4,647 / week

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from $664 / night

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19

Vacation villa in St. Jean

St. Barts / St. Jean

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The Greek villa, ideally located on the heights of Colombier, offers extraordinary ocean views. Dominant entirely Flemish sea and bay, swimming pool overlooks the ocean. tranquility lovers will be delighted by the privacy and quiet of this villa. The two chambers situat …see more

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from $795 / night

$5,566 / week

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from $795 / night

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32

Vacation villa with swimming pool in Gustavia

St. Barts / Gustavia

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 500 mi
  • Swimming pool
This villa, located in Gustavia, is ideal for 8 vacationers. It offers 4 bedrooms, a private pool, an enclosed garden and WiFi. The lounge is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book or take advantage of th …see more

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from $1,103 / night

$7,746 - $11,030 / week

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Responds fast!
avg. 1 hour 25 minutes

from $1,103 / night

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6

St. Jean Vacation home rental

St. Barts / St. Jean

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
LSF - is located in Camaruche and offers a splendid view over Marigot Bay, Turtle Island and the ocean. This delightful villa is comprised of two buildings. The main building consists of the living, kitchen, and dining areas. The two bedrooms are located in a separate …see more

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from $330 / night

$2,311 / week

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from $330 / night

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Leeward
St. Jean
Pointe Milou
Gustavia
Marigot
Anse des Flamands
Lurin
Anse de Lorient
Petit Cul de Sac
Anse des Cayes
Gouverneur
Toiny
Grand Cul-de-Sac
Grand Fond
Corossol
Colombier
Salines