Windward Apartments, Estates and cottages

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157 Holiday homes

18

Holiday home in Windward

Windward / Morne Criquet

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
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  …see more

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16

Holiday villa in Windward

Windward / Marigot

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
La Belle Epoque is located in Marigot at a walking distance from the beautiful Grand Cul de Sac lagoon, and the beach..  …see more

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19

Marigot holiday villa rental

Windward / Marigot

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Blue Indies is a brand new villa ideally located within a walking distance to Marechale beach, a very private beach near..  …see more

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14

Holiday home in Windward

Windward / Morne Criquet

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
Surrounded by flowering purple bougainvillea and yellow frangipani, Villa VEL answers this tropical profusion of colors with bursts of blue: turquoise, azure, powder, and sky. With a view over St. Barth's green hillsides and the Atlantic in the distance, this relax  …see more

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18

Holiday home rental

Windward / Morne Criquet

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
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

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11

Windward holiday villa rental

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Grand Carenage is a villa located in Pointe Milou facing the ocean and the sunset.This two bedroom villa has a large ope..  …see more

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12

Holiday villa in Windward

Windward / Marigot

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Nearest beach Marigot Gustavia 15 min.Restaurant 5 min. Supermarket 5 min. Airport 10 min.  …see more

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20

Holiday villa in Windward

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
The villa Roy is a 4 bedroom villa located in the hillside of Vitet. The villa has an amazing view on the lagoon of Gran..  …see more

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10

Holiday home in Windward

Windward / Vitet

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
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

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16

Holiday villa with swimming pool in Windward

Windward / Pointe Milou

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Jane JMS is a unique hideaway perched in complete privacy on a beautiful hillside in Pointe Milou, St Barts. The v..  …see more

from £690 / night

£4830 / week

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from £690 / night

24

Holiday home in Vitet

Windward / Vitet

3 3 Min stay varies

  • 3 bedrooms
  • Sleeps 3
  • Min stay varies
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

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11

Holiday villa in Vitet

Windward / Vitet

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
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

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24

Holiday home in Windward

Windward / Morne Criquet

3 3 Min stay varies

  • 3 bedrooms
  • Sleeps 3
  • Min stay varies
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

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14

Holiday villa in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Phoenix is a villa located in Pointe Milou facing the ocean and the sunset.This two bedroom villa has a large open living room open onto a terrace and a pool.The two bedrooms have an ocean view.  …see more

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14

Pointe Milou holiday villa rental

Windward / Pointe Milou

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa BBE is a charming one bedroom villa that can be rented individually or can be combined with the adjacent Villa Car..  …see more

from £309 / night

£2160 / week

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from £309 / night

20

Holiday villa in Windward

Windward / Marigot

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Amelie KAM perched on the Marigot hillside offers a splendid view over Marigot bay. It features two bedrooms, two..  …see more

from £1012 / night

£7080 / week

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from £1012 / night

12

Holiday villa accommodation

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
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

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20

Pointe Milou holiday villa rental

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Milou KID, located in Pointe Milou, has two bedrooms, two bathrooms and a pool. Stone steps lead to the villa that..  …see more

from £729 / night

£5100 / week

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from £729 / night

12

Holiday villa in Lorient

Windward / Lorient

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Les Jardins dEmmanuel EMM has two bedrooms, two bathrooms and a pool. Located in Lorient, this villa offers a spen..  …see more

from £643 / night

£4500 / week

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from £643 / night

24

Holiday home in Windward

Windward / Morne Criquet

5 7 Min stay varies

  • 5 bedrooms
  • Sleeps 7
  • Min stay varies
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

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9

Petite Saline holiday villa rental

Windward / Petite Saline

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa 21 is a villa located on the hillside of Lorient, close to Petite Saline.This very private villa has a stunned ocean view of Lorient Bay and the islands of quotFrgatequot, quotToc Vertquot and quotBonhommequot.  …see more

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19

Windward holiday villa rental

Windward / Petite Saline

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
quotMurrayaquot is a brand new villa located on the heights of Petite Saline. The villa is hidden in a tropical garden.T..  …see more

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13

Holiday villa rental

Windward / Pointe Milou

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Perched above the ocean with panoramic views of the bays of Lorient, St. Jean, Anse des Cayes, and St. Maarten, sits Vil..  …see more

from £412 / night

£2880 - £3480 / week

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from £412 / night

9

Holiday villa with swimming pool in Windward

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Pastel EBA is a little gem, situated in the Vitet countryside with pastoral and ocean views. Simplistic in style,..  …see more

from £986 / night

£6900 / week

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from £986 / night

10

Windward holiday villa rental

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Hidden Treasures DKD The setting of this villa so captures your fantasy of a tropical island paradise that Hollywood cou..  …see more

from £540 / night

£3780 - £6120 / week

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from £540 / night

19

Villa rental in Marigot

Windward / Marigot

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
Bellevue is located hillside on Marigot.This brand new villa has a panoramic view on Marigot bay and the ocean.This roo..  …see more

from £986 / night

£6900 - £10500 / week

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from £986 / night

24

Home rental in Windward

Windward / Morne Criquet

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
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

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(1) Excellent 

6

Holiday villa with swimming pool in Windward

Windward / Marigot

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Architectural Designers island hideaway overlooking beautiful Marigot Bay and its undiscovered beach, Villa Case et Cuis..  …see more

from £369 / night

£2580 / week

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from £369 / night

19

Windward holiday villa rental

Windward / Vitet

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
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

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9

Holiday villa letting

Windward / Vitet

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
“Alouette” is a villa perched on the hillside of Vitet, overlooking the ocean. This one bedroom villa with a pool is a very affordable budget for a vacation on the island.  …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

5

Windward / Pointe Milou

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £407 / night

£2440 - £6098 / week

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from £407 / night

13

Holiday villa with swimming pool in Windward

Windward / Lorient

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Indigo Orchid TOR is a newly built and charming one bedroom villa in Lorient, St Barts that can be rented individu..  …see more

from £360 / night

£2520 / week

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from £360 / night

24

Holiday home rental

Windward / Morne Criquet

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
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

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11

Windward holiday villa rental

Windward / Petite Saline

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Harry is a brand new 2 bedroom, 2 bathroom villa located in Saline, overlooking the ocean and hillside area.This t..  …see more

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15

Holiday villa in Vitet

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The beautiful Villa Anais AIA in Vitet, at the center of the eastern half of St. Barts, offers guests spectacular views..  …see more

from £495 / night

£3465 / week

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from £495 / night

24

Holiday home in Morne Criquet

Windward / Morne Criquet

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
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

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18

Holiday home in Windward

Windward / Morne Criquet

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
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

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15

Holiday villa rental

Windward / Lorient

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Villa Adore ADR is simple beachfront villa under one roof in Lorient, St Barts. There is a great yard and easy access to..  …see more

from £378 / night

£2640 / week

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from £378 / night

20

Holiday villa with swimming pool in Windward

Windward / Camaruche

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Kaiteki LUZ was built with privacy and relaxation in mind. Perfect for families and large groups, it is built on t..  …see more

from £566 / night

£3960 - £5544 / week

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from £566 / night

8

Holiday villa rental

Windward / Lorient

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sea Breeze EZE is a very quiet and peaceful Lorient, St Barts, villa with beautiful palms, the sounds of water lapping a..  …see more

from £498 / night

£3480 / week

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from £498 / night