50 Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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1,246 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

from $207 / night

$1,446 / week

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from $207 / night

(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

from $473 / night

$4,031 / week

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Responds fast!
avg. 1 hour 40 minutes

from $473 / night

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

from $568 / night

$3,974 / week

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from $568 / night

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

from $568 / night

$3,976 / week

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from $568 / night

(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

from $2,571 / night

$55,000 / week

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from $2,571 / night

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

from $1,071 / night

$22,000 / week

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from $1,071 / night

(5) Excellent 

23

Vacation cottage with shared 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

from $801 / night

$5,603 / week

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from $801 / night

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

from $590 / night

$4,130 / week

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from $590 / night

17

Vacation villa with swimming pool in Anse des Flamands

St. Barts / Anse des Flamands

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A beautiful sea view welcomes you to Villa Ti Lama. This villa, a room is composed of two units very nicely decorated, where wood predominates. The large room is air-conditioned and independent. The terrace by the pool with the view of the sea, St Barth, is a call for r …see more

from $444 / night

$3,110 - $17,158 / week

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from $444 / night

(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

from $805 / night

$5,635 / week

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from $805 / night

(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

from $173 / night

$968 / week

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Responds fast!
avg. 2 hours 49 minutes

from $173 / night

(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

from $559 / night

$3,910 / week

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Responds fast!
avg. 31 minutes

from $559 / night

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

from $354 / night

$2,478 / week

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from $354 / night

(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

from $723 / night

$17,000 / week

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from $723 / night

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

from $440 / night

$2,419 / week

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from $440 / night

(2) 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

from $1,071 / night

$25,000 / week

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from $1,071 / night

(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

from $647 / night

$4,524 / week

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Responds fast!
avg. 31 minutes

from $647 / night

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

from $439 / night

$3,072 / week

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from $439 / night

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

from $856 / night

$5,992 / week

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from $856 / night

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

from $311 / night

$2,073 - $5,470 / week

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from $311 / night

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

from $1,000 / night

$16,500 / week

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from $1,000 / night

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

from $2,857 / night

$70,000 / week

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from $2,857 / night

33

St. Jean Vacation villa rental

St. Barts / St. Jean

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
Welcome to our brand new Villa Le Moulin. The villa offers 3 bedrooms, 3 bathrooms, a brand-new pool and a private access to the beach. The villa is surrounded by a lush tropical garden and is built around an old mill, where the master bedroom is located. Le Moulin is …see more

from $1,715 / night

$35,000 / week

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from $1,715 / night

(2) 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

from $2,286 / night

$22,000 / week

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from $2,286 / night

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

from $801 / night

$5,597 / week

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from $801 / night

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

from $428 / night

$2,995 / week

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from $428 / night

(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

from $967 / night

$6,763 / week

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from $967 / night

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

from $1,715 / night

$35,000 / week

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from $1,715 / night

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

from $712 / night

$4,982 / week

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from $712 / night

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

from $334 / night

$2,338 / week

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from $334 / night

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

from $1,116 / night

$11,159 / week

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Responds fast!
avg. 2 hours 4 minutes

from $1,116 / night

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

from $1,786 / night

$40,000 / week

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from $1,786 / night

59

Villa rental in Anse des Cayes with swimming pool, golf nearby

St. Barts / Anse des Cayes

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This villa, located in Saint-Barthélemy, is ideal for 4 vacationers. It offers 2 bedrooms, a private pool, a terrace and WiFi. The lounge is perfect for unwinding after a day in the sun. Curl up on the comfortable sofa and enjoy a good book or take advantage of the ame …see more

from $1,021 / night

$13,389 / week

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Responds fast!
avg. 2 hours 15 minutes

from $1,021 / night

26

Vacation villa in Colombier

St. Barts / Colombier

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
Welcome to our villa Desire, is a stunning villa located on the Colombier hillside guaranteeing a perfect privacy and offering one of the most beautiful view on Gustavia harbour, where you never grow tired of admiring the ballet incessant of the luxury yachts and the dr …see more

from $2,143 / night

$40,000 / week

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from $2,143 / night

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

from $1,020 / night

$7,140 - $39,729 / week

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from $1,020 / night

14

Vacation villa with swimming pool in Anse des Flamands

St. Barts / Anse des Flamands

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Datcha is a beautiful villa of St Barth with contemporary charm, located on the heights of Flamands with a beautiful sea view and very close to Gustavia (restaurants, shopping ...) The rooms of identical size and comfort all have a sea view, a private terrace and are i …see more

from $830 / night

$5,297 - $23,031 / week

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from $830 / night

12

Vacation villa rental

St. Barts / Anse des Cayes

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
Welcome to our beautiful 2 bedroom villa Key Lime that is situated on the beach of Anse des Cayes in St Barts. The villa offers great sea vies with direct access to the beach at Anse des Cayes. Key Lime has a beautiful décor with warm colours and modern style througho …see more

from $450 / night

$8,925 / week

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from $450 / night

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

from $173 / night

$968 / week

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Responds fast!
avg. 2 hours 49 minutes

from $173 / night

22

Gustavia Vacation home rental

St. Barts / Gustavia

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
Typical Case St barth new int and ext with small garden parking large deck of 30m2 covered terrace dining room and kitchen equipe al americaine beautifully decorated a haven of peace a few steps from the beach of Cove Cove and the surf spot of cove lzards 10 m drive fro …see more

from $173 / night

$1,207 / week

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from $173 / night

8

Vacation cottage rental

St. Barts / St. Jean

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Air conditioning
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

from $794 / night

$5,554 / week

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from $794 / night