50 Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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1,246 Vacation rentals

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 $322 / night

$1954 - $5286 / week

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from $322 / 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 $1715 / night

$12000 - $32000 / week

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from $1715 / 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 $1071 / night

$7500 - $22001 / week

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from $1071 / 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

$5060 - $22700 / 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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(1) 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 $662 / night

$4634 / week

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from $662 / night

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(1) 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 $174 / night

$974 / week

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Responds fast!
avg. 2 hours 14 minutes

from $174 / night

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(1) Excellent 

10

St. Jean Vacation cottage rental

St. Barts / St. Jean

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Le Cottage de Charme STEVE avec sa piscine privée est situé sur les hauteurs de Marigot, avec une très belle 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 …see more

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from $367 / night

$2566 / week

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Responds fast!
avg. 3 hours 46 minutes

from $367 / night

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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 $2571 / night

$18000 - $55000 / week

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from $2571 / 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 $1000 / night

$7000 - $16500 / week

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from $1000 / night

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32

Villa rental in St. Jean with shared pool

St. Barts / St. Jean

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa fully air-conditioned, consisting of two bedrooms with shower room, living room with fully equipped kitchen. Outside, a teak terrace, a large dining table, pool. Outdoor parking for two vehicles. Wifi Air conditioning in all rooms services are included: Transfer f …see more

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from $348 / night

$2435 - $12753 / week

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from $348 / night

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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

$1446 / week

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from $207 / 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 $426 / night

$4022 / week

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Responds fast!
avg. 2 hours 38 minutes

from $426 / 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 $1071 / night

$7500 - $25000 / week

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from $1071 / 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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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 $442 / night

$3092 / week

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from $442 / night

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(4) Excellent 

12

Vacation villa with swimming pool in Colombier

St. Barts / Colombier

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
  • 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 $487 / night

$3115 - $3544 / week

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from $487 / night

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16

Vacation apartment rental

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Duplex holiday apartment in St Jean consisting in a two bedrooms with ensuite bathroom, a living room dining room with fully equipped American kitchen, a terrace with a magnificent sea on the Bay of St Jean and the Eden Rock Hotel. Great Localisation in the center of …see more

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from $428 / night

$3000 - $8000 / week

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from $428 / night

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30

Vacation villa with swimming pool in Gustavia

St. Barts / Gustavia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Located in gorgeous Gustavia, this bright villa is perfectly located for exploring the tropical island of St. Barths, promising an unforgettable holiday for up to 8 people. The plush living space is ideal for relaxing after a day in the sun. Enjoy a good book or one of …see more

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from $1054 / night

$7375 - $21067 / week

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Responds fast!
avg. 3 hours 7 minutes

from $1054 / night

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(1) Excellent 

15

Vacation villa rental

Anse des Flamands / Flamands Beach

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Villa Triagoz is a private villa offered for vacation rental at the delightful St Barts. When you arrive, prepare to be blown away by the beauty of the place. With a private heated pool, three Rooms (two Master bedrooms,+one baby room), Villa Triagoz is a single floor v …see more

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from $600 / night

$4200 - $22001 / week

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from $600 / night

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4

Vacation bungalow in Gustavia

St. Barts / Gustavia

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
The Chalet is a cocoon corner, independent with all amenities needed to accommodate you. Screwless opinion, with a large bed 2 places.Cuisine equipped with coffee. a lounge to relax and a quiet terrace allows you to eat outside in tranquility 1 min walk to the beach to …see more

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from $82 / night

$569 / week

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from $82 / 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 $2857 / night

$20000 - $70000 / week

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from $2857 / 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 $799 / night

$5585 / week

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from $799 / night

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20

Vacation villa with swimming pool in Gustavia

St. Barts / Gustavia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $567 / night

$3966 / week

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from $567 / night

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80

Villa rental in St. Jean

St. Barts / St. Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
At the center of the island, ideally located Bikini villa has 3 bedrooms with their shower room. A fully equipped kitchen is the center of the main living room that can be closed and fully air-condition or completely open to the terrace. A large dining table inside and …see more

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from $415 / night

$2900 - $15000 / week

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from $415 / night

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(1) Excellent 

21

Villa rental in St. Jean with shared pool

St. Barts / St. Jean

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Have you ever dreamed of being caressed by trade winds taking your breakfast, well our covered terrace equipped with a jacuzzi allows you to live that dream. Indeed at Villa Beaulieu everything is done to ensure comfort and relaxation. Just steps from this haven of peac …see more

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from $273 / night

$1908 - $5795 / week

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from $273 / night

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22

Home rental in Gustavia with swimming pool

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Located on glitzy St. Barthélemy, this modern house offers the perfect base for exploring the everything the island has to offer. It can easily accommodate 4 sun-loving holidaymakers. Facing the sea and 500 metres from local shops, sights and restaurants, this beautif …see more

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from $469 / night

$3266 - $12688 / week

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Responds fast!
avg. 3 hours 7 minutes

from $469 / night

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74

Vacation villa in Gustavia

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Villa Vaea 2 bedrooms St Barts offers an amazing view of the ocean and the sunset. Overlooking ocean and located in a peaceful area of St Barts, this villa is completely relaxing and a real oasis of calm and serenity just a few minutes from St Jean. It makes the locati …see more

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from $414 / night

$2900 - $13680 / week

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from $414 / night

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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

$4130 / week

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from $590 / night

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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 $2286 / night

$16000 - $45000 / week

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from $2286 / 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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58

Gustavia Vacation villa rental

St. Barts / Gustavia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Ideally located in Flamands, close to Gustavia, the beach of Flamands, the hotels and restaurants, this villa rental offers a beautiful view on the hills of Flamands and the Bay. With two dining areas and a bedroom with a direct access to the living room. Each bedroom …see more

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from $857 / night

$6000 - $28500 / week

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from $857 / night

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33

Gustavia Vacation villa rental

St. Barts / Gustavia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villas-apartments are located in a private and serene environment, nestled in a green valley just minutes Flemings St Barthélemy. Featuring a collection of eight elegant accommodations and equipped with every comfort, "Vacation Villas Apartments Rentals" offers a new an …see more

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from $793 / night

$5551 / week

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from $793 / night

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75

Vacation villa in Gustavia

St. Barts / Gustavia

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
Villa Vaea 1 bedroom St Barts offers an amazing view of the ocean and the sunset. Overlooking ocean and located in a peaceful area of St Barts, this villa is completely relaxing and a real oasis of calm and serenity just a few minutes from St Jean. It makes the locatio …see more

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from $385 / night

$2700 - $13680 / week

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from $385 / night

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50

Vacation villa in Gustavia

St. Barts / Gustavia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Villa Miki 1 Bedroom St Barts is idealy located one minute drive away from Gustavia and Shell Beach This holiday home offers a serene atmosphere at highly reasonable rates. The villa is a perfect combination of value, luxury and comfort. Your family or your group of fr …see more

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from $486 / night

$3400 - $14215 / week

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from $486 / 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 $1786 / night

$12500 - $40000 / week

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from $1786 / night

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35

Vacation villa in Gustavia

St. Barts / Gustavia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Villa Mahea 3 bedroom,superb home located at the hills of St Jean, St Barts Villa Mahea privately located four bedrooms, nestled in a quiet and calm area of St jean. Promotion: car included in low season 2017 Features: Hillside, Privacy, Seaview Details: Nestled in a …see more

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from $1257 / night

$8800 - $41040 / week

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from $1257 / night

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52

Vacation penthouse in Gustavia

St. Barts / Gustavia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary
Luxurious Penthouse with a total area of ​​352 m² included terraces, full exposure EST (Sunrise), located on the 4th floor, with 3 bedrooms and 3 bathrooms, modern kitchen, guest toilet, terraces with 2 levels , garage space, exceptional view of the Gustavia harbor, ful …see more

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from $564 / night

$4746 - $18815 / week

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from $564 / night

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58

Vacation villa in Gustavia

St. Barts / Gustavia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Ideally located in Flamands, close to Gustavia, the beach of Flamands, the hotels and restaurants, this villa rental offers a beautiful view on the hills of Flamands and the Bay. With two dining areas and a bedroom with a direct access to the living room. Each bedroom …see more

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from $714 / night

$5000 - $28500 / week

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from $714 / 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

$2995 / week

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from $428 / night

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35

Gustavia Vacation villa rental

St. Barts / Gustavia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Nestled in a quiet and calm area of St jean. A few minutes drive away from the beach, shops, restaurants Beautiful view over the hills of St Jean. Villa Mahea is modern and offers a contemporary design Maheais built on two levels. First level is composed of a kitchen op …see more

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from $1164 / night

$8150 - $41040 / week

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from $1164 / night

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(1) Excellent 

6

St. Jean Vacation cottage rental

St. Barts / St. Jean

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Le Cottage de Charme CINDY est situé sur les hauteurs de Marigot, avec une vue sur la mer, au calme. Cottage de Charme pour 2 personnes, avec sa grande terrasse en Deck privative, Prestation de qualité, Non Fumeur, Chambre tout confort, climatisée, Lit king size, salle …see more

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from $264 / night

$1843 / week

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Responds fast!
avg. 3 hours 46 minutes

from $264 / night

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22

Vacation home with swimming pool in St. Jean

St. Barts / St. Jean

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning
VILLA Nikaia Nikaia is an immaculate conception. Never villa will incarnate as purely dream of whiter than white ... White is white! At VITET HEATED POOL SEA VIEW IDEAL FOR TRAVELERS OF MARRIAGE RETREAT meditative A contemporary building made of simple and elegant geome …see more

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from $600 / night

$4200 - $15000 / week

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from $600 / night

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