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158 Holiday homes in Windward

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23 Photos

Villa | 1 Bedroom | sleeps 2

7 Nights min stay

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from £173 /night

£1205 - £2711 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Villa Ti RĂªve, literally meaning "little dream", is a real haven of peace located in Grand Cul de Sac with undeniably everything to offer for a stylish, relaxing holiday.  …see more

7 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

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from £414 /night

£2892 - £15061 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Makasi offers a chic, secluded and serene retreat on St Barth.  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £345 /night

£2410 - £12049 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
It features 3 large and private beautiful bedrooms, all with their own well-designed bathrooms  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £646 /night

£4519 - £20091 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Hillside of Marigot, Villa Imagine is a luxurious and brand-new 3 bedroom villa with gorgeous sea views over the Grand Cul de Sac lagoon and its turquoise waters that you can enjoy from both inside and out.  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £422 /night

£2952 - £9519 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Located on the heights of Pointe Milou, one of the most popular areas of St Barth, Villa Mandarine offers an amazing panoramic view on the sea toward Lorient and St Jean bays and the exceptional opportunity to enjoy both sunrise and sunset  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 3

7 Nights min stay

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from £158 /night

£1106 - £2952 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Villa Coral is a lovely 2 bedroom villa, ideal for a couple with a child.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £237 /night

£1657 - £6025 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Located on the heights of Grand Cul de Sac, Villa Nilmath is a beautiful 2 bedroom villa with a gorgeous view over the lagoon of Grand Cul de Sac.  …see more

15 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £523 /night

£3657 - £10543 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Located on the heights of Vitet, with a nice sea view, Villa Victoria is a sumptuous 2 bedroom villa offers contemporary design and a particularly neat decoration.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

6 Nights min stay

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from £302 /night

£2109 - £3916 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Kiara, recently renovated, is an elegant 2 bedroom* villa located on the secluded neighbourhood of Vitet.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

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from £266 /night

£1860 - £6061 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Villa Kermao is a fantastic 5 bedrooms / 4 bathrooms villa, with lots of charm, privacy and peacefulness.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £1050 /night

£7347 - £25717 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Aureve is a gorgeous 4 bedroom villa is without a doubt a luxury villa that offers all the high end standards and much more.  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

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from £2754 /night

£19278 - £96386 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Villa La Plage on St. Barts is one of the most sought after beachfront estates on the island. Located directly on Lorient Beach, this stunning villa offers 7 bedrooms, each with an ensuite bath. Discounts may apply for 2 week bookings or longer  …see more

11 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £215 /night

£1500 - £4200 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
One of our two bedroom villas the most rented A full privacy A very attractive budgetAlta Vista is a villa nestled on the hillside of Vitet.A stunning ocean view, a full privacy, a pool overlooking the ocean, a perfect villa to recharge ones batteries.  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £373 /night

£2607 - £4059 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
St Barts Villa Casa Blanca is located on the hillside of Grand Cul de Sac. It has a beautiful view on the lagoon of Peti..  …see more

12 Photos

Villa | 1 Bedroom | sleeps 2

Min stay varies

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from £253 /night

£1770 - £4050 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Sea Dream is located on the estate of villa Captiva in Marigot.This separate brand new bungalow is perfectly equipped an..  …see more

19 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £283 /night

£1980 - £4950 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
St Barts Villa Oceana is a very private villa, located hillside at the far end of Vitet.This villa is perfect for the na..  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

Min stay varies

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from £1226 /night

£8580 - £26202 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
One of our biggest villas One of our most private villas One of the villas the most requestedThe villa La Vie en Rose is..  …see more

16 Photos

Villa | 1 Bedroom | sleeps 2

Min stay varies

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from £300 /night

£2100 - £5880 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
La Belle Epoque is located in Marigot at a walking distance from the beautiful Grand Cul de Sac lagoon, and the beach..  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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from £343 /night

£2400 - £3120 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
St Barts Villa Carmen is a new villa on the hillside of Vitet. Contemporary, modern, this spacious villa opens to a larg..  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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from £763 /night

£5340 - £16200 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
This is a great villa La Rose des Vents is a pure Caribbean island villa .It is a brand new white colonial villa, with..  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
The villa quotKhajurahoquot is a contemporary private 3 bedroom villa located in Pointe Milou.The villa has an amazing v..  …see more

13 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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from £806 /night

£5640 - £16800 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Villa Le Roc is located on the highest point of the private estate of Le Domaine du Levant in Petit Cul de Sac.This su..  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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from £652 /night

£4560 - £7380 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Summer Breeze is a villa located on the heights of Grand Cul de Sac, at a short walk from the beach of the lagoon.The vi..  …see more

8 Photos

Villa | 1 Bedroom | sleeps 2

Min stay varies

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from £138 /night

£960 - £1620 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Bois Joli is a charming little Caribbean villa located on the heights of Vitet in St Barts.It offers a panoramic view on..  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £729 /night

£5100 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
Villa Milou KID, located in Pointe Milou, has two bedrooms, two bathrooms and a pool. Stone steps lead to the villa that..  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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from £875 /night

£6120 - £10980 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Domingue is located on the sunset side ocean view of La Pointe Milou .This villa has all the assets to seduce you The..  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £257 /night

£1794 - £2394 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
Villa Belle Etoile AMS Close to Lorients shops and beach in Camaruche, this charming villa sits in a very convenient loc..  …see more

19 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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from £840 /night

£5880 - £24000 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Blue Indies is a brand new villa ideally located within a walking distance to Marechale beach, a very private beach near..  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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from £399 /night

£2790 - £11700 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Ange Bleu is a five bedroom villa located on the hillside of Petit Cul de Sac.It has a stunning view on the ocean. The large living and terrace make this villa ideal for family vacations.  …see more

19 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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from £432 /night

£3024 - £10710 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Chambord is one of our favourite villas which we advise you if you wish a total privacy, with a magnificent view on the..  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Villa Far Caraibes FAR is an elegant and comfortable 3 bedroom, 3 bathroom villa located on the hillside of Grand Cul d..  …see more

17 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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from £1200 /night

£8400 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
La Corniche DAY is located 150 feet above the water at the tip of Pointe Milou, St Barts, with panoramic views all the w..  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £489 /night

£3420 - £5280 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
La Carette CAR is a very private and spectacular villa with a large pool and excellent views of Lorient, St Barts. Bedro..  …see more

12 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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from £523 /night

£3660 - £12540 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Bel Ombre is located in Marigot overlooking the ocean.The villa is open on the ocean located below. A large terrace is e..  …see more

19 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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from £772 /night

£5400 - £15000 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
quotMurrayaquot is a brand new villa located on the heights of Petite Saline. The villa is hidden in a tropical garden.T..  …see more

16 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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from £1372 /night

£9600 - £21600 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Captiva property is a located in Marigot at the edge of the sea. It is composed by the villas Captiva and Sea DreamThe..  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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from £686 /night

£4800 - £15000 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Located on the hillside of Camaruche,Agave is one of the most private villas offering one of the greatest views of the i..  …see more

20 Photos

Villa | 9 Bedrooms | sleeps 18

Min stay varies

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
Banane BAN A secret estate, a confidential address, a unique intimate atmosphere. A privileged place where you unpack yo..  …see more

19 Photos

Villa | 3 Bedrooms | sleeps 6

Min stay varies

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from £840 /night

£5880 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
Villa Abby ABB is a very private and sensational villa set high in Vitet, St Barts. Abby offers guests some of St. Barth..  …see more

11 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £429 /night

£3000 - £9000 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Bali is one of our most requested two bedroom villaIt is located hillside in Pointe Milou facing the sunset, and the o..  …see more

10 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £540 /night

£3780 - £6120 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
Hidden Treasures DKD The setting of this villa so captures your fantasy of a tropical island paradise that Hollywood cou..  …see more

13 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £217 /night

£1518 - £2242 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Face la Mer is located on the beach of the lagoon of Grand Cul de Sac.From the lounge chairs on the sandy beach admire..  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

Min stay varies

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from £1543 /night

£10800 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Villa Les Embruns JMG is located at the far end of Flamands beach, overlooking the ocean and facing Bonhomme island. Wat..  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Villa Sky SKI is one of the most spacious, comfortable houses in St. Barths. Relax with afternoon tea or cocktails and e..  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

Min stay varies

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from £3429 /night

£24000 - £72000 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Right on the very beautiful beach of Lorient, in a garden of 0.74 acre with big coconut palms swinging with the trade winds, this roomy brand new villa on the beach is one of more beautiful architectural success of the island .  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
Villa Om AOM is located in the exclusive private gated community of Mont Jean on the north side of the island. The impre..  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 8

Min stay varies

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from £1500 /night

£10500 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
Beverly BEV is an elegant and very private villa located on Mt. Jean, St Barts. This 4 bedroom villa offers privacy and..  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

Min stay varies

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from £2143 /night

£15000 - £48000 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Villa Avenstar St Barts is made of five bedrooms, five bathrooms, and two pools. This amazing villa is located in the hi..  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £326 /night

£2280 - £3180 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Les Sables is a very nice villa extreamly well located on Lorient beach.It has a nice pool and offers a great privacy.  …see more

12 Photos

Villa | 2 Bedrooms | sleeps 4

Min stay varies

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from £249 /night

£1740 - £3360 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • Pets welcome
Aliz dEden is located on the hillside of Pointe Milou.The villa has an ocean view of the ocean and the sunset.The livin..  …see more