Windward Apartments, Estates and cottages

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18 properties
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Windward

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157 Holiday homes

19

Holiday home in Morne Criquet

Windward / Morne Criquet

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
Part of the centrally located Les Terrasses (HAL) apartment complex, the comfortably furnished HAL is a spacious ground floor unit with views from its private terrace of the lush hillsides surrounding St. Jean and of the Atlantic Ocean from the communal pool and sun ...  …see more

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24

Home letting in Windward

Windward / Morne Criquet

3 3 Min stay varies

  • 3 bedrooms
  • Sleeps 3
  • Min stay varies
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 be  …see more

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20

Windward holiday villa rental

Windward / Pointe Milou

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Bon Temps BTR Built in Palladianstyle adapted to the tropics, Bon Temps BTR is a six bedroom villa located on the west s..  …see more

from £2143 / night

£15000 - £18000 / week

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from £2143 / night

20

Windward holiday villa rental

Windward / Mont Jean

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
Nearest beach Lorient, MarigotGustavia 15 min.Restaurant 10 min.Supermarket 10 min.Airport 10 min.  …see more

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11

Villa rental in Pointe Milou

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Bali is one of our most requested two bedroom villaIt is located hillside in Pointe Milou facing the sunset, and the o..  …see more

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15

Holiday villa in Pointe Milou

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa LAbricotier DOR is located in Pointe Milou, St Barts, with a spectacular view of the ocean. This villa is tasteful..  …see more

from £738 / night

£5160 / week

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from £738 / night

20

Holiday villa rental

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Villa Samsara AMA Situated high above the ocean, with a panoramic western view in Pointe Milou, St. Barth is the spectac..  …see more

from £463 / night

£3240 - £5100 / week

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from £463 / night

20

Lorient holiday villa rental

Windward / Lorient

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Luz is a charming villa located in Lorient and facing the sunset. This villa is composed by 2 floors. On the fi..  …see more

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12

Holiday villa in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
One of favourite two bedroom villas One of our villas the most rentedVilla Cest la Vue is hung between the sky and the..  …see more

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19

Holiday villa rental

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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

from £840 / night

£5880 / week

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from £840 / night

12

Windward holiday villa rental

Windward / Marigot

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
One of our favourite villas One of our villas with at a walking distance to the beach Villa Escapade is located on the h..  …see more

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18

Holiday villa in Marigot

Windward / Marigot

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
One of our villas with a private access to the seaCaptiva is a located in Marigot at the edge of the sea.The villa, on t..  …see more

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19

Holiday villa in Vitet

Windward / Vitet

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
One of our favourites villas One of our villas the most private One of our spacious villasThe villa quotVinaquot is situ..  …see more

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18

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
Nestled in the hillside of Vitet, “Villa Tranquille” is a very private, very quiet three-bedroom villa surrounded by tropical gardens with breathtaking views over the turquoise lagoon of Grand Cul de Sac, Petit Cul de Sac, Mont Jean and the surrounding islan  …see more

from £540 / night

£3780 - £11500 / week

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from £540 / night

16

Windward / Pointe Milou

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children

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from £351 / night

£2455 / week

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from £351 / night

18

Windward holiday villa rental

Windward / Pointe Milou

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
One of our favourites villas One of our biggest villas One of the nicest pools of the islandThe villa Valentina is locat..  …see more

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10

Windward holiday villa rental

Windward / Lorient

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
The villa Escape is located in Lorient, at few steps away from the beach. The pool and the Jacuzzi are surrounded by a d..  …see more

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24

Windward holiday home rental

Windward / Morne Criquet

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
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

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20

Holiday villa in Mont Jean

Windward / Mont Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Charming and private, Villa SIB PAR is located on the Mont Jean hillside, St Barts. The villa has 3 bedrooms and can be..  …see more

from £1543 / night

£10800 / week

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from £1543 / night

13

Holiday villa in Pointe Milou

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa quotZionquot is located in the sunset side of la quotPointe Milouquot.It is a brand new villa who combine all the..  …see more

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23

Morne Criquet holiday home rental

Windward / Morne Criquet

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
With a wrap-around terrace for taking in the view east over Marigot Bay and Tortue, and a refreshing pool to escape the heat, the outdoor space at Villa Eagle of the Sea (LSF) offers a great way to spend a day. The convenient Camaruche location means you're not far  …see more

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14

Villa rental in Windward

Windward / Vitet

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Au Cur du Rocher is a brand new two bedroom villa located on the hillside in Marigot.The villa has a living open on a..  …see more

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20

Holiday villa in Windward

Windward / Pointe Milou

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
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

from £875 / night

£6120 - £10980 / week

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from £875 / night

20

Windward holiday villa rental

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
This manicured tropical paradise is an exclusive and perfect hideaway located on an unspoiled piece of land of 2 acre.Su..  …see more

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24

Windward holiday home rental

Windward / Vitet

3 3 Min stay varies

  • 3 bedrooms
  • Sleeps 3
  • Min stay varies
This newly renovated villa offers a superb 180-degree view over the ocean, Marigot bay and Isle Tortue. The spacious living room opens onto the a terrace and heated pool overlooking the sea. Caressed by the ocean breezes, Villa VPB is well-exposed to the sun all day ...  …see more

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20

Villa rental in Windward

Windward / Pointe Milou

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
quotAu Ventquot is an exclusive property overhanging the cliff in Pointe Milou.You will be stunned by the panoramic view..  …see more

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20

Windward holiday villa rental

Windward / Pointe Milou

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
QuotLinquot is a villa located in Pointe Milou, surrounded by a large garden, with an ocean view toward the sunset. This 03 bedroom villa is perfect for the affordable budget.The living room is open onto a terrace with a nice ocean view.  …see more

from £386 / night

£2700 - £3465 / week

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from £386 / night

16

Mont Jean holiday villa rental

Windward / Mont Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Armor is a villa located in the private estate of Montjean, close to Pointe Milou area.Built at the top of the hill, th..  …see more

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18

Holiday villa in Vitet

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
quotCasa Azulquot has a superb ocean viewThis renovation project villa is located on the top of Vitet and has a panorami..  …see more

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16

Holiday villa in Marigot

Windward / Marigot

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
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

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20

Holiday villa rental

Windward / Mont Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Nearest beach Marigot, LorientGustavia 15 min.Restaurant 10 min.Supermarket 10 min.Airport 10 min.  …see more

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20

Holiday villa with swimming pool in Mont Jean

Windward / Mont Jean

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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

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20

Holiday villa with swimming pool in Windward

Windward / Lorient

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Banane BAN A secret estate, a confidential address, a unique intimate atmosphere. A privileged place where you unpack yo..  …see more

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24

Windward holiday home rental

Windward / Morne Criquet

3 3 Min stay varies

  • 3 bedrooms
  • Sleeps 3
  • Min stay varies
Located high on a St. Jean hilltop, the aptly named Villa Super Sky (BBA) provides rare character for a St. Barth home, partly for its blend of stone walls with all-natural fabrics and decor, and partly for its spacious terrace and two pools. All bedrooms are fairly ...  …see more

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21

Holiday home in Vitet

Windward / Vitet

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
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

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20

Holiday villa in Windward

Windward / Petite Saline

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Dunes is certainly the most spectacular villa in StBarts With its 16,000 sq. ft new property, villa Dunes will sed..  …see more

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12

Villa rental in Marigot

Windward / Marigot

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
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

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