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135 Holiday homes in Windward

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  • St. Barts Clear
  • Windward Clear
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  • Grand Fond (10)
  • Lorient (8)
  • Morne Criquet (26)
  • Petit Cul de Sac (85)
  • Vitet (6)

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135 Results  |  
24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £1711 /night

£11977 - £23953 / week

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Key info:

  • Not suitable for children
  • No pets allowed
With some of the most exquisite landscaping on the island, Villa ADO enjoys a feeling of serenity while being centrally located. The gardens, terraces and pool of this St. Jean hillside villa offer many places for quiet relaxation, as well as a view of St. Jean Bay, ...  …see more

16 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £214 /night

£1498 - £5390 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa les Lataniers (REL) is located high above St. Jean, with a great view and a convenient location. The living area and bedrooms are decorated in a bright and airy style, with wood tones and with fabrics. This is a great house for families or two couples sharing a...  …see more

13 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £214 /night

£1498 - £4192 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Located in exclusive community of Pointe Milou, Villa Little Caramba (BBE) is a charming, one-bedroom studio-style villa that can be rented individually or can be combined with the nearby two-bedroom Villa Caramba (MBA). Villa Little Caramba's integrated living and b...  …see more

24 Photos

House | 1 Bedroom | sleeps 1

14 Nights min stay

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from £313 /night

£2186 / 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

19 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £514 /night

£3593 - £5390 / 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

House | 5 Bedrooms | sleeps 5

5 Nights min stay

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from £3850 /night

£26947 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Located in the exclusive and secluded community of Domaine du Levant, Villa Indian Song (IND) is composed of seven separate units in a tropical hillside garden leading down to a secluded white sand beach. The centrally located main house offers comfortable and conven...  …see more

23 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £488 /night

£3414 - £9581 / 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 | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £685 /night

£4791 - £23953 / 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

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £1155 /night

£8084 - £10480 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated at the top of the hill overlooking Flamands Bay, Villa Arte (ATT) is a newly constructed villa that offers its guests a high degree of luxury and comfort along with sensible design perfectly suited for the vacation lifestyle. From the property's ample and pa...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £529 /night

£3698 - £5726 / 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 | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £685 /night

£4791 - £10480 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Vigie (GRE) is a wonderful villa perched on the cliff promontory over the east end of St. Jean Bay. The cozy and comfortable living area opens onto the terrace, pool and view. Conveniently located between Lorient and St. Jean village, Villa GRE is in close prox...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £385 /night

£2695 - £9581 / 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 | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £3422 /night

£23953 - £28743 / week

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Key info:

  • Not suitable for children
  • No pets allowed
With its fabulous location directly on the beach at Flamands and its exquisite yet understated style, Villa Ela is a study in the beautiful simplicity of Caribbean living. Overlooking the multi-tiered hardwood terrace and large pool, the property's main house compris...  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £642 /night

£4492 - £15569 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Sous la Falaise (SOU) is nestled just above the water at the eastern end of St. Jean Beach. Separate cottages offer a superb view of the white-sand beach, the bay, and the islets farther off the coast. This private and well-situated villa is within easy walking...  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £1284 /night

£8983 - £17965 / 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 | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £257 /night

£1797 - £5989 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Carefully decorated in a welcoming, casual-chic style, Harbor Haven provides our guests with a unique opportunity for experiencing St. Barth a different way. Situated right in the heart of Gustavia, with a magical view out over the harbor and the boats at their moori...  …see more

24 Photos

House | 6 Bedrooms | sleeps 6

5 Nights min stay

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from £1882 /night

£13174 - £17965 / 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 | 4 Bedrooms | sleeps 5

5 Nights min stay

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from £899 /night

£6288 - £23953 / week

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Key info:

  • Not suitable for children
  • No pets allowed
With exceptionally fine craftsmanship and top quality furnishings and appliances, Villa Valentina (VIP) makes every day of a St. Barth vacation even more pleasurable. Located in Pointe Milou overlooking the Atlantic to the east, this property is bathed in sunlight al...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £420 /night

£2935 - £7785 / 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

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £428 /night

£2995 - £11977 / 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 | 5 Bedrooms | sleeps 7

5 Nights min stay

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from £1275 /night

£8923 - £11917 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Ideally located on the western Camaruche hillside over Lorient Bay, Villa Cumulus (CML) stands out as one of the most remarkable new properties on the island, combining high-quality craftsmanship and contemporary design with numerous ecological features and convenien...  …see more

24 Photos

House | 6 Bedrooms | sleeps 6

5 Nights min stay

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from £2139 /night

£14971 - £21557 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Crossing the threshold into Villa Good News (BMR) will seem to you like walking into another world. In this expansive, skylit space, standing on a gleaming white marble floor and surrounded by an exceptional collection of Beaux Arts antiques, you feel as if you've en...  …see more

22 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £492 /night

£3444 - £8983 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Located in Pointe Milou, Villa Ananda (KID) is a bright and cheerful home perfect for friends traveling together. The atmosphere is airy and open, and the layout of the bedrooms and the indoor and outdoor livings areas affords privacy while offering plenty of space f...  …see more

12 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

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from £291 /night

£2036 - £3593 / 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

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £805 /night

£5629 - £17306 / week

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Key info:

  • Not suitable for children
  • No pets allowed
With its main living area open on three sides to the sun and breezes and panoramic view, Villa Blue Heaven (FUN) envelops you in the essence of St. Barth living. Decorated in classic West Indies blue and white, this is the iconic island home. The layout of this spaci...  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £480 /night

£3354 - £5330 / 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

23 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £668 /night

£4671 - £18563 / 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

22 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £514 /night

£3593 - £11677 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Bord de Mer (BDM) is an elegant, West Indies style villa surrounded by lush tropical flora, just a one-minute stroll via its own private path to the beautiful, white-sand beach of St Jean. The spacious interior is decorated with dark wood antiques and light fab...  …see more

24 Photos

House | 2 Bedrooms | sleeps 3

5 Nights min stay

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from £582 /night

£4072 - £19162 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated in the quiet hillside neighborhood of Petite Saline, looking out over the picturesque Lorient Bay, Villa Sea Dreams (AXS) offers modern comfort and stunning views. From this high vista, you can see the far western end of St. Barth as well as the islands of S...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £407 /night

£2845 - £11078 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Maracuja (MJA) blends the beauty of Caribbean surroundings with the peaceful ambience of Asian decor. Looking east over the Atlantic from high on a hillside in Vitet, this home is a favorite of many Sibarth's guests who have fallen in love with its unique charm...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £471 /night

£3294 - £7486 / 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 | 5 Bedrooms | sleeps 5

5 Nights min stay

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from £2738 /night

£19162 - £25150 / 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 £1198 /night

£8384 - £28743 / 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 | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £856 /night

£5989 - £19971 / 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 | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £770 /night

£5390 - £5989 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated in the private and gated community of Domaine du Levant in Petit Cul de Sac, Villa Lagon Vert (LAV) is a brand new construction with sophisticated design and an exceptional view. Furnished in a clean, contemporary style, this 3-bedroom home provides its gues...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £471 /night

£3294 - £3893 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Splashes of color in the Asian-inspired decor and artworks enliven the serene atmosphere at Casa Zenial (Villa KAS). From its rare Saline location, Villa KAS looks out over swaying palm fronds at the valley of Grand Saline, the dunes beside the beach, and the blue Ca...  …see more

16 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £497 /night

£3474 - £12575 / 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 | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £1219 /night

£8533 - £23204 / 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

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £557 /night

£3893 - £12815 / 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 £514 /night

£3593 - £14971 / 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

11 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £300 /night

£2096 - £5989 / 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

24 Photos

House | 5 Bedrooms | sleeps 5

5 Nights min stay

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from £1284 /night

£8983 - £17965 / 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 £1198 /night

£8384 - £26947 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Villa Fleur de Cactus (FLE) is a brand-new property high on the Lurin hillside offering a spendid view over the ocean with year-round sunsets. This home incorporates a number of glamourous features of design and architecture, such as a wall-size Michelangelo detail a...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

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from £300 /night

£2096 - £7186 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Beautiful grounds, an awesome view, and a fabulous location close to the beach just begin to describe the advantages of "the good life" at Villa Maribart (BAR). From the mahogany furnishings to the beautiful tiled floors, antiques, and original lithographs, the list ...  …see more

24 Photos

House | 2 Bedrooms | sleeps 3

5 Nights min stay

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from £565 /night

£3953 - £10000 / 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

15 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £899 /night

£6288 - £19462 / 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 | 2 Bedrooms | sleeps 2

5 Nights min stay

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from £642 /night

£4492 - £8384 / 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 | 4 Bedrooms | sleeps 4

5 Nights min stay

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from £634 /night

£4432 - £17366 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Located high in Vitet, with an incredible view over Cul de Sac and Tortue island, Villa Bibi (BIB) offers peace, privacy, and beauty. Built and furnished using natural materials such as dark Brazilian wood and white cotton canvas, the overall effect gives Villa BIB a...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

7 Nights min stay

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from £1198 /night

£8384 - £19162 / 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 | 5 Bedrooms | sleeps 5

5 Nights min stay

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from £873 /night

£6108 - £23114 / 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