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384 Holiday homes in Windward

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Location

  • St. Barts Clear
  • Windward Clear
  • All towns
  • Anse de Lorient (10)
  • Camaruche (26)
  • Grand Cul de Sac (16)
  • Grand Fond (28)
  • Grande Saline (1)
  • Lorient (17)
  • Marigot (21)
  • Mont Jean (23)
  • Morne Criquet (34)
  • Petit Cul de Sac (103)
  • Petite Saline (9)
  • Pointe Milou (57)
  • Toiny (6)
  • Vitet (33)

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384 Results  |  
24 Photos

House | 1 Bedroom | sleeps 1

14 Nights min stay

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from £305 /night

£2135 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Located in the apartment complex of Les Terrasses on the hillside of St. Jean, ARD offers a wonderful view of the bay of St. Jean, convenience to the shops and restaurants in St. Jean Village, and the enjoyment of the large communal pool and sun deck. This one-bedroo...  …see more

12 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £285 /night

£1989 - £3509 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Located at the far end of Pelican Beach, at the opposite end of St. Jean from the airport, Villa CHG is a delightful beach house typical of traditional St. Barth style. Step off the shady back porch of your home-by-the-sea and your feet are in the sand--just on the o...  …see more

21 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £249 /night

£1737 - £2515 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Ideally located in Pointe Milou, facing St. Barth's windward side, Turtle Island, and the Atlantic Ocean, Villa Bonbonniere is sunlit and breezy. The villa's open and airy living room features large and comfortable off-white sofas facing the terrace, the pool and the...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £293 /night

£2047 - £7018 / week

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Key info:

  • Not suitable for children
  • No pets allowed
With wonderful, west-facing views over Lorient Bay, Les Cases (LIN) is a simple, yet very comfortably furnished villa offering classic St. Barth living in a relaxed and rustic setting. The open living area looks out over the terrace and view, and the pool is situated...  …see more

19 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £276 /night

£1930 - £4971 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa CHO commands spectacular views of St. Barth's eastern end from its vantage point high on a hillside in Vitet. From nearly every room in this house you can look out over the bays of Grand and Petit Cul de Sac and the open ocean beyond. The villa is painted and d...  …see more

13 Photos

House | 1 Bedroom | sleeps 1

14 Nights min stay

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from £460 /night

£3217 / week

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Key info:

  • Not suitable for children
  • No pets allowed
On a hillside overlooking the picturesque bay of Grand Cul de Sac, Villa Bamboo (AAA) brings you a little bit of paradise in a traditional St. Barth way. Open and breezy, this home is perfectly suited to unwinding and enjoying a true escape from reality. From the ope...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £544 /night

£3802 - £12515 / week

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Key info:

  • Not suitable for children
  • No pets allowed
From up in the hills of the secluded neighborhood of Vitet, Villa Abby (ABB) looks out over the islets of Tortue, Toc Vert, and Fregate, as well as Marigot Bay and Petit and Grand Cul de Sac. Comfortable indoor and outdoor living and dining areas make this villa an i...  …see more

13 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £376 /night

£2632 - £4386 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Bathed in sunlight at its Pointe Milou vantage point over the sea, Villa C'est la Vue (CLV) celebrates St. Barth's Caribbean beauty in a lighthearted explosion of color. Comfortably furnished and well appointed, Villa CLV will lift your spirits the moment you enter. ...  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £669 /night

£4679 - £9942 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
La Vigie is a 4 bedroom villa located on the cliffs with a fabulous view over St. Jean bay. The villa has a lovely terrace with a pool and plenty of areas for relaxation and enjoying the view. The interior spaces include a large and fully air-conditioned dining area opening onto the covered terrace and a well-equipped kitchen leading from the living area, also with access to the terrace.  …see more

23 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £468 /night

£3275 - £9357 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Perched high on a west-facing hillside in Pointe Milou, Villa Safari (ARI) provides a panoramic view of the Atlantic coast of St. Barth all the way from Lorient Bay to Anse de Cayes as well as the island of St. Maarten in the distance. And while the view may be capti...  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £585 /night

£4094 - £16375 / week

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Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
Armor is a 3 bedroom villa has wonderful ocean views, tropical garden and is very private. Armor is a Caribbean resort villa located in the greatly prized private estate of Montjean, close to Pointe Milou area in St Barts.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £402 /night

£2808 - £8188 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Bali is a 2 bedroom villa offering ocean and sunset views and a covered pool.  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £376 /night

£2632 - £9357 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
"Au Coeur du Rocher" is a luxurious, 2 bedroom villa, located on the hillside of Vitet, overlooking Marigot and Pointe-Milou. Very elegant & private the villa offers a dramatic view over the ocean and surrounding landscape.  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

14 Nights min stay

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from £2340 /night

£16375 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Looking out over the blue Atlantic from the prestigious peninsula neighborhood of Pointe Milou, Villa Sea Breeze brings refined elegance to the dramatic setting of St. Barth's Côte Sauvage. Decorated in a comfortable and yet sophisticated colonial style, this propert...  …see more

21 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £341 /night

£2383 - £3709 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Similar in design and furnishings to its neighboring bungalows, Villa Val André and Villa Cap Frehél, Villa Dahouët (RLD1) is the ideal spot for those seeking a picture-perfect spot for a St. Barth idyll. Right on the beach at the far end of St. Jean Bay, Villa RLD1 ...  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £2507 /night

£17544 - £57018 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Papaye is a 4 bedroom villa with ocean view, direct access to the beach and is very private.  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £585 /night

£4094 - £14620 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Cocoland (LAN) is a spectacular Pointe Milou property with dramatic sunset views, one of the most popular two-bedroom villas on St. Barth. Thoughtfully designed and maintained to very high standards, this is an ideal villa for two couples desiring equal bedroom...  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

14 Nights min stay

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from £3843 /night

£26901 / week

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Key info:

  • Not suitable for children
  • No pets allowed
High up in the hillside neighborhood of Vitet, overlooking Petite Cul de Sac to the north and Grand Fond to the south, Villa Angel (LHV) provides relaxing comfort with a modern, Caribbean flair. From the outside, the design reflects the simple lines of traditional We...  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £544 /night

£3802 - £11112 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Florence is a 3 bedroom villa with rooms that open to the outside, making it perfect for vacations with friends. The villa offers privacy and ocean views.  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £193 /night

£1346 - £6433 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Flora is a charming French Caribbean home located in Camaruche with a beautiful view over Marigot Bay. Very comfortable and tastefully decorated the villa has 2 bedrooms with en-suite bathrooms completely independent of each other, a living room opening to the terrace and the view and an outdoor, covered living area and terrace with large pool. Surrounded by lush tropical gardens, the villa is extremely private and just a 5 minute drive to Lorient Beach.  …see more

18 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £159 /night

£1112 - £2749 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa BRO - This recently renovated 1 bedroom, 1 bathroom apartment is part of "Les Terrasses" condominium complex, located on the top of St-Jean. This lovely property is ideally located between the beautiful beaches of St-Jean and Saline. Just two minute drive away ...  …see more

24 Photos

Villa | 1 Bedroom | sleeps 2

5 Nights min stay

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from £251 /night

£1755 - £4971 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Buddha Bay is a 1 bedroom villa on the beach with outdoor living space and a jacuzzi.  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £669 /night

£4679 - £23392 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Ocean's 5 (CEL) is clean and crisp with modern elegance and charm, offering spectacular views over the ocean and the nearby island of Bonhomme. Located on the hillside above the Flamands Bay, this home is convenient to town as well as to the nearby beach's fabu...  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £3342 /night

£23392 - £61404 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Indian Song is a 5 bedroom villa with ocean views and tennis and beach nearby.  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £1254 /night

£8772 - £17544 / week

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Key info:

  • Not suitable for children
  • No pets allowed
The stone path at the entryway to Villa Hill House (BOW) leads to a choice: On your right, a jaw-dropping view of the Atlantic, the islands of Tintamarre and Anguilla visible in the distance. On your left, a home so inviting and elegant that it rivals the natural bea...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £468 /night

£3275 - £5205 / week

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Key info:

  • Not suitable for children
  • No pets allowed
On the west-facing hillside of Pointe Milou, Villa Samsara (AMA) is perfectly situated for indulging in sun-filled days and spectacular sunsets. Decor of honey-colored Java teak and thoughtfully selected artwork and fabrics lends Villa AMA a particularly warm ambienc...  …see more

22 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £460 /night

£3217 - £9357 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Ever Sail (BOT) is a delightful modern villa sitting high above Grand Cul de Sac, with superb ocean views. The craftsmanship and the extensive use of teak along with the furnishings lend a unique nautical feel to this villa. In design and style, this home manag...  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £552 /night

£3860 - £7310 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Luz is a 3 bedroom villa with a long lap pool and beautiful ocean and sunset views.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £301 /night

£2106 - £7018 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Mirande is a 3 bedroom villa offering ocean and sunset views.  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £544 /night

£3802 - £14620 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Diamond (DIA) welcomes its guests into a perfect world of thoughtful and stylish design. Built in 2012, this property benefits from the informed experience of an owner who knows exactly what visitors to St. Barth need. On a centrally located hillside overlookin...  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £344 /night

£2406 - £9006 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Escape is a very private 3 bedroom villa just a few steps from the beach and has a pool and jacuzzi surrounded by a tropical garden.  …see more

23 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £652 /night

£4562 - £18129 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Khajuraho (KHA), situated in Pointe Milou, features splendid views over the surrounding islands, the ocean and St. Barth's famous sunsets. This home takes full advantage of its great hillside location by offering ocean views from all the rooms. The large living...  …see more

24 Photos

House | 5 Bedrooms | sleeps 5

5 Nights min stay

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from £853 /night

£5965 - £22574 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Remarkably open and airy, Villa Vina (VNA) is composed of separate cottages in a marvelously landscaped and natural garden. With a living an dining area completely open on three sides and perfectly integrated with the outdoor space, terrace and pool, this villa is ma...  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

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from £485 /night

£3392 - £8772 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Villa Nita with its retro 60s décor is very stylish, has a superb view and a convenient central location in Lorient.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £422 /night

£2948 - £10439 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Chambord is a 3 bedroom villa offering ocean views, privacy, heated pool and jacuzzi.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £209 /night

£1462 - £4094 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Alta Vista is a very private 2 bedroom villa that offers stunning views of the ocean, lagoon and nearby islands.  …see more

19 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £502 /night

£3509 - £5264 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Decorated in a a clean, simple style employing shades of white and natural wood accents, Villa Beach House (FAY) is a dreamlike idyll right on the remote and peaceful western end of Flamands Beach. The living area and kitchen open directly onto the teak deck, where a...  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £460 /night

£3217 - £10527 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Located within walking distance from Marigot Beach, Marigot Bay has 2 bedrooms.  …see more

24 Photos

House | 6 Bedrooms | sleeps 6

5 Nights min stay

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from £1741 /night

£12186 - £16925 / week

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Key info:

  • Not suitable for children
  • No pets allowed
The aptly-named Villa Seascape (SEE) sits right on Pointe-Milou hillside with a breathtaking 180-degree ocean view and a private access to the beach in the cove below. This luxurious and chic property is designed with living areas and bedrooms on two levels, providin...  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £1170 /night

£8188 - £28071 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Looking out from a hillside in Vitet, Casa Tigre (TGR) enjoys a wide vista over the clear water of Grand Cul de Sac and the blue Atlantic beyond. The villa's design melds modernity and tradition, resulting a peaceful and pleasant atmosphere that invites you to relax ...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £356 /night

£2486 - £7603 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Surrounded by a garden of hibiscus, cactus, and flambouyant trees, Villa La Carette (CAR) is a place for a true tropical escapism. The colorful exterior and magnificent wide ocean view are balanced by a soothing interior decor of rattan, dark hardwoods, and smooth te...  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

4 Nights min stay

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from £1254 /night

£8772 - £14620 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Directly overlooking the ocean and right across from the Eden Rock Hôtel, Reef Point is a beautiful contemporary 3 bedroom villa.  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £443 /night

£3100 - £11462 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Nestled on the tranquil hillside of St. Jean, Villa Kir Royal (KRL) is a recently renovated property within walking distance of the village's beach, shops and restaurants. Set amid a verdant tropical garden and looking out over the bay of St. Jean and the Atlantic Oc...  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

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from £669 /night

£4679 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Captain Cook is a 4 bedroom (suites) villa with ocean views and heated pool and jacuzzi.  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £368 /night

£2574 - £9240 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa (CLI) is located on the peak of Camaruche, St Barts, hillside with a view over Marigot, Cul de Sac and Mont Jean. A very open villa combining Asian, Chinese and African styles. The living area has a beautiful dark rattan weaved sofa with rich reddish brown over...  …see more

11 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £1103 /night

£7720 - £19942 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
La Plantation is a 3 bedroom villa offering views of the the privacy and a large pool.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £276 /night

£1930 - £4825 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Oceana is a 2 bedroom villa with an ocean view.  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £376 /night

£2632 - £9357 / week

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Key info:

  • Not suitable for children
  • No pets allowed
High in the hills of Vitet, Villa Au Coeur du Rocher (ACR) offers the kind of simple sophistication that can make a St. Barth vacation comfortable, relaxing and carefree. With a magnificent view over the surrounding landscape and the wide Atlantic, this newly built p...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £341 /night

£2383 - £5592 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Val André (RLD2) is one of those places that visitors to St. Barth gaze at and think, "I wish I were there." Located at the far end of St. Jean beach, this lovely retreat looks out over the expanse of the bay, the waves breaking on the reef and the Atlantic Oce...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £627 /night

£4386 - £8188 / week

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Key info:

  • Not suitable for children
  • No pets allowed
At the crest of the hill that tops the exclusive Pointe Milou neighborhood, Villa Seaweed (SEA) expresses itself in unique and thoughtful designs in every way possible: landscaping, architecture and decor. The path to the house is flanked by a sea of fountain plants ...  …see more