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135 Holiday homes in Windward

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  • Grand Fond (10)
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135 Results  |  
11 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £311 /night

£2174 - £6212 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Do Dragan (VDD) is a newly built home just steps from the pure, white sand of Flamand Beach. This lovely villa offers space and comfort. The living and dining areas open onto the pool, terrace and beachfront view. You can enjoy hearing the sound of the waves wh...  …see more

18 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £169 /night

£1181 - £2920 / 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

15 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £932 /night

£6522 - £20187 / week

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Key info:

  • Not suitable for children
  • No pets allowed
As St. Barth neighbors go, you could not be in better company than you will find here. At the eastern end of the gleaming crescent of Flamands Beach, you are among some of the finest villas and hotels on the island. When you enter Villa TCK you are presented with a b...  …see more

24 Photos

House | 6 Bedrooms | sleeps 6

5 Nights min stay

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from £1953 /night

£13665 - £18634 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated on the western side of the peninsula of Pointe Milou, Villa Bon Temps (BTR) offers a gracious lifestyle in the perfect Caribbean setting, amid lush tropical foliage and with unparalleled sunset views. From the vantage point of the expansive and elegantly des...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £400 /night

£2796 - £4038 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Kiara House (MEM) brings to St. Barth a rare touch of design inspiration that sets it apart from the crowd. Blonde-wood flooring, blue-painted wainscoting and an eclectic blend of the modern and the vintage give this remarkable villa a Hamptons feel that has made it ...  …see more

24 Photos

House | 5 Bedrooms | sleeps 5

14 Nights min stay

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from £3505 /night

£24535 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Stroll down a short path among flowering bougainvillea and gardenias, and soon you arrive at the sunny central court of Villa Tatiana (TIA), with its Japanese-inspired teak deck and shimmering pool. Classic Richard Schultz-designed chaises tempt you to soak up the su...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £444 /night

£3106 - £12423 / week

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Key info:

  • Not suitable for children
  • No pets allowed
From the vista of Villa Surf View (SUR), looking out over the Caribbean and the unspoiled hills of the island's Côte Sauvage, you can see a vision of St. Barth's simpler past while enjoying the creature comforts of the present. Decorated with an efficient yet imagina...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £548 /night

£3836 - £5940 / 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 | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £533 /night

£3727 - £15528 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated above Flamands Bay, Villa Rivendell (RIV) looks out over the green of the surrounding hills and the blue the Atlantic beyond, with Ile Bonhomme and Ile le Boulanger visible in the distance. Villa RIV has just undergone a complete renovation, and now boasts a...  …see more

21 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £362 /night

£2531 - £3940 / 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

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £391 /night

£2733 - £9814 / 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

13 Photos

House | 1 Bedroom | sleeps 1

14 Nights min stay

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from £489 /night

£3417 / 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 | 5 Bedrooms | sleeps 5

5 Nights min stay

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from £2840 /night

£19876 - £26087 / week

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Key info:

  • Not suitable for children
  • No pets allowed
La Danse des Etoiles (Villa DOL) is an extraordinary achievement of design and craftsmanship. The exquisite melding of wood and stone throughout this home creates a cool and relaxing atmosphere and combines with the carefully selected furnishings to make Villa DOL on...  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £604 /night

£4224 - £18634 / week

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Key info:

  • Not suitable for children
  • No pets allowed
La Rose des Vents (Villa LRV) offers a sensational view of the lagoon at Grand Cul de Sac. The white decor and open-air feel add to its ambiance. This home's recent renovation reflects the vibrant blue and green hues of the sea, an idyllic atmosphere for relaxation. ...  …see more

12 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £302 /night

£2112 - £3727 / 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 | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £430 /night

£3007 - £12423 / week

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Key info:

  • Not suitable for children
  • No pets allowed
From a high vantage point on the hillside of St. Jean, Villa Isia (LIS) looks out over a breathtaking expanse of clear, blue water to the islets in the distance. Chic and modern in design and decor, and with advantages like a well-equipped kitchen (wine cellar availa...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £489 /night

£3417 - £7454 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This newly built villa directly on the beach at Lorient is sure to become one of the most popular vacation rentals on the island. Smartly laid-out and decorated in a simple, appealing style, Villa Sandra & Jessica (SAJ) offers guests a combination of quality furnishi...  …see more

24 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £222 /night

£1553 - £3013 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Located at the entrance to Pointe Milou is the charming Villa Colibri (COL). The bedroom overlooks the ocean and comes furnished with a 4-poster bed with mosquito netting. The small living area is separated from the kitchen by a counter. Guests spend more time on the...  …see more

10 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £213 /night

£1491 - £3665 / week

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Key info:

  • Not suitable for children
  • No pets allowed
On a lush hillside overlooking Marigot Bay and its lovely beach, Villa Case et Cuisine blends island comfort with casual sophistication and provides a perfect vacation retreat for couples or families with children. The main terrace with its teak table and chairs is i...  …see more

18 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £125 /night

£870 - £1740 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Just a one-minute stroll from the white sands of St. Jean Beach, you will find Villa CAP among the palms, a quaint island bungalow that invites you to relax and dream of simpler times. Surrounded by flowering gardens, the ambiance of this villa is one of classic West...  …see more

24 Photos

House | 5 Bedrooms | sleeps 5

5 Nights min stay

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from £1331 /night

£9317 - £18634 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Eternity (ETY) is a large and luxurious property on Flamands hillside, offering lovely views of the sea and conveniently situated just a short drive from the beach and its fabulous restaurants. The ideal vacation home for those who love to entertain in style, V...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £577 /night

£4038 - £13292 / 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

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £888 /night

£6212 - £20715 / week

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Key info:

  • Not suitable for children
  • No pets allowed
The aptly named Villa Imagine looks out over a wide expanse of tropical sea and sky from near the crest of the hill over Marigot. This delightful home offers a rare blend of simplicity and style, with a layout that makes the most of a great location and tasteful furn...  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

14 Nights min stay

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from £2485 /night

£17392 / 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

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £507 /night

£3544 - £6392 / week

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Key info:

  • Not suitable for children
  • No pets allowed
From the wrap-around balcony of Villa Vialenc (VIA), guests enjoy the iconic St. Barth view of the harbor with all its charm and fascination for boat-lovers. Named for its mid-20th-century resident, the islands first doctor, Villa VIA is a piece of St. Barth history,...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £489 /night

£3417 - £7764 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Luz was built with privacy and relaxation in mind. Perfect for families and groups of friends, it is built on three different levels with views over beautiful Lorient Bay. A large built-in BBQ and dining area is perfect for entertaining at lunch or dinner. Gorg...  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £1265 /night

£8851 - £24069 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Named for the Hindu goddess of wealth, love and spiritual prosperity, who is believed to be the embodiment of beauty, Villa Lakshmi (LLA) is itself a temple of beauty, a place where guests will marvel at their good fortune of having landed in this lovely corner of St...  …see more

23 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £693 /night

£4845 - £19255 / 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 | 6 Bedrooms | sleeps 6

5 Nights min stay

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from £1849 /night

£12943 - £17976 / 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

19 Photos

House | 1 Bedroom | sleeps 2

5 Nights min stay

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from £329 /night

£2299 - £4348 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Overlooking the bay of St. Jean, Villa Namaste (AUM) is spacious and comfortable with fabulous sunsets views. When you enter the house, on your right you find the large and open living area, nicely decorated with hardwood furniture and African art. The living room ov...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £630 /night

£4410 - £21429 / week

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Key info:

  • Not suitable for children
  • No pets allowed
The entrance to Villa REP is the kind where you kick off your shoes before going in. Perhaps you've stopped off at the fish market in the nearby village of Lorient, so you're headed for the kitchen. Or maybe you're just back from an afternoon at Saline beach, ready f...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

7 Nights min stay

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from £1243 /night

£8696 - £19876 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Created by the renowned St. Barth design firm of Olivier Dain Perspectives, Villa Six offers a truly masterful combination of contemporary lines and exquisite comfort in an ideal location. At the summit of the peninsula of Pointe Milou, this property is truly one of ...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £435 /night

£3044 - £8075 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Perched high on Colombier hillside, Villa Grain de Folie (GDF) offers a splendid view over Gustavia, the islands of Saba and St. Eustatius, and brilliant Caribbean sunsets. The villa is tastefully decorated in a contemporary style. From the living room and the kitche...  …see more

21 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £622 /night

£4348 - £12423 / week

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Key info:

  • Not suitable for children
  • No pets allowed
KAM named villa Amelie perched on the Marigot hillside offers a splendid view over Marigot bay. It features two bedrooms, two bathrooms, a solar heated pool and a heated Jacuzzi. This lovely villa has a charming character thanks to a chic and ethnic style mixed with ...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £1154 /night

£8075 - £15528 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Reef Point (RFP) boasts one of the finest locations on the island. At the very farthest point of the end end of St. Jean Bay, Villa RFP looks down over the clear blue water and out over the curve of the white sand beach. Recently built and decorated in contempo...  …see more

24 Photos

House | 6 Bedrooms | sleeps 6

5 Nights min stay

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from £977 /night

£6833 - £27951 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Located on the hillside between Camaruche and Marigot, with a sprawling view over the countryside and ocean, Villa Eclipse (JNM) is luxurious and architecturally innovative. Its design is based on clear-cut straight lines and angles, combined with the extensive use o...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £666 /night

£4659 - £8696 / 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

24 Photos

House | 2 Bedrooms | sleeps 3

5 Nights min stay

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from £586 /night

£4100 - £10373 / week

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Key info:

  • Not suitable for children
  • No pets allowed
One of the real gems of Pointe Milou, Villa Mandarine Bleue (LEA) is provides a 270-degree view, affording its guests the rare opportunity to enjoy both sunrise and sunset. With a color scheme of blue and white, the villa is cheerful and extremely comfortable. Villa ...  …see more

16 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £515 /night

£3603 - £13044 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Petit Lagon (APL) enjoys breathtaking views of the bay of Petit Cul de Sac from its perfect vantage point in the gated community of Domaine du Levant. A colorful and stylish decor lends Villa APL a cheerful atmosphere, and the private beach only a two-minute st...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £577 /night

£4038 - £15528 / 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

House | 5 Bedrooms | sleeps 5

5 Nights min stay

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from £1598 /night

£11181 - £12423 / week

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Key info:

  • Not suitable for children
  • No pets allowed
La Vie en Rose (Villa SUN) provides the best of both worlds for its guests: vast, sun-drenched outdoor spaces balanced by cool and shaded interiors. Located in Petite Cul de Sac, this property is perfect for entertaining, offering plentiful seating around the large p...  …see more

24 Photos

House | 3 Bedrooms | sleeps 4

5 Nights min stay

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from £666 /night

£4659 - £15528 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Light and bright, wide open interior spaces and a large and uniquely shaped pool make Villa MEL perfect for kids or for anyone who feels like smiling and having fun. Surrounded by royal palms and drenched in sun all day long, this home is the kind of villa that famil...  …see more

20 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £231 /night

£1615 - £4969 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Ecoute les Vagues (VMG) is a lovely 3 bedroom beachfront villa, located on Flamands beach, just a few steps from the blue water and white sand. This charming property offers a peaceful retreat from everyday stress. You will enjoy taking a nap while hearing the song o...  …see more

23 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £506 /night

£3541 - £9938 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa L'Abricotier (DOR) combines the picture-postcard image of a Caribbean holiday--a sunny terrace, shimmering pool, and blue ocean--with a rare and inviting interior design accentuating warm and welcoming colors and a relaxing, suffuse light. Located in the presti...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £231 /night

£1615 - £8013 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Kyody (KDY) is a very attractive South American style villa located on the Marigot hillside. It has lovely views over all Grand Cul de Sac, Tortue Island and the ocean. Recently renovated both inside and outside. A pool and wooden deck blend in perfectly with t...  …see more

23 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £497 /night

£3479 - £9938 / 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

20 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £107 /night

£746 - £1522 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa SJA's unique situation creates a rare opportunity for those looking for the ultimate in convenience. Just yards away from a white-sand beach, and easy walking distance from the supermarkets and bakery in Lorient, this home allows you to spend your days the way ...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £338 /night

£2361 - £4907 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Les Sables (CHL) indulges its guests with best of all worlds: a terrace just steps from the sea, green lawns and swaying palms, a refreshing pool, and classic Caribbean comfort. This property's charm and convenient Lorient location make it ideal for both couple...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £426 /night

£2982 - £21740 / week

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Key info:

  • Not suitable for children
  • No pets allowed
High on the hillside of St. Jean, hidden among frangipani and flambouyant trees, Villa Terre Indigo (BOR) offers well-appointed and smartly designed comfort for those in search of an island retreat with a magnificent view. You enter the villa straight into the breezy...  …see more

18 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £284 /night

£1988 - £4100 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Located above Lorient Bay and offering a dramatic view over the ocean and the surrounding islands, Villa Tortue (TOR) pampers its guests with contemporary design and elegant furnishings. The integrated living area and bedroom open onto the bright terrace, inviting in...  …see more