50 Best Vacation Rentals in Windward - Holiday Lettings - Cabins

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Pointe Milou
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Vitet
29 properties
Morne Criquet
26 properties
Marigot
18 properties
Lorient
14 properties
Mont Jean
12 properties
Camaruche
10 properties
Petite Saline
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Windward

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157 Vacation rentals

18

Vacation 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 d  …see more

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19

Windward Vacation 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 nature lovers and the amateurs of full privacy The villa has an unspoiled view on Toiny bay and the ocean.Nearest beach Marigot, Lorient, Petit Cul de S  …see more

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(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 $492 / night

$2951 - $7378 / week

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from $492 / night

19

Marigot Vacation 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 the Guanahani Hotel and Spa. The lagoon of Grand Cul de Sac. The beach restaurant of the Guanahani Hotel. The tennis court of the Guanahani Hotel.Thi  …see more

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24

Vacation 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 contemporar  …see more

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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 beauty  …see more

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14

Vacation 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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24

Vacation 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 terra  …see more

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18

Vacation 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 infin  …see more

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8

Vacation 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 and St. Martin in the distance. It is only a few meters from Lorient Beach. There is an indoor and outdoor dining and a nice deck on two levels with a  …see more

from $597 / night

$4176 / week

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from $597 / night

8

Windward Vacation villa rental

Windward / Marigot

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
Bois Joli is a charming little Caribbean villa located on the heights of Vitet in St Barts.It offers a panoramic view on the bay of Marigot, Tortue island and Grand Cul de Sac lagoon is marvellous.A swimming pool, surrounded by large rocks, overlooks the ocean.This very  …see more

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18

Vacation 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 In  …see more

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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 roomy villa is perfect to meet large families with friends to celebrate events.The living is extremely spacious and is open on a very long lap pool.Each  …see more

from $1183 / night

$8280 - $12600 / week

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from $1183 / night

9

Vacation 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, the villa has been constructed using modern materials such as wood, polished concrete, steel and glass, while at the same time keeping a traditional i  …see more

from $1183 / night

$8280 / week

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from $1183 / night

11

Windward Vacation 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 tastefully decorated villa features the living room, dining room, fully equipped kitchen, two bedrooms with its ensuite bathrooms, spacious terrace and  …see more

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12

Vacation 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 living room and the two bedrooms open onto the pool and terrace, offering an ocean view from all rooms.BEDROOMView: Ocean Equipment: air con  …see more

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12

Vacation villa in Windward

Windward / Marigot

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Marigot is a small area on the eastern end of St Barts with a small beach. Marigot has some famous residents and is also close to Grand Cul de Sac which has several beach restaurants and watersports.BEDROOMView: Marigot beach Equipment: air conditioning,  …see more

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20

Vacation 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 Cap Au Vent MOZ Located on a cliff at the very tip of Pointe Milou, St Barts chicest neighborhood, Villa Cap au Vent MOZ is truly one of the most deluxe and extraordinary villas on St. Barts. Totally private, surrounded by the ocean and its breezes, Villa Cap au V  …see more

from $3060 / night

$21420 / week

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from $3060 / night

15

Vacation villa with swimming pool in Windward

Windward / Lorient

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Raia RIA is located directly on Lorient Beach, one can hear the sound of the waves lapping against the shore. The beach is quite calm and there are constant breezes. With mosquito netting in both bedrooms, it is possible to sleep with just the breezes. This villa  …see more

from $772 / night

$5400 / week

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from $772 / night

24

Vacation home in Windward

Windward / Vitet

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
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 the  …see more

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16

Vacation 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 of Marchale. The public access to these beaches is by the beautiful garden of the hotel Guanahani close by. The villa is surrounded by a very nice tro  …see more

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20

Vacation 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 Grand Cul de Sac.This villa recently redone and refurnished has a new deck on which two palm trees are swinging by the trade winds.You will enjoy the kitc  …see more

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20

Vacation villa in Windward

Windward / Pointe Milou

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Captain Cook is one of our largest villas. It is located in the private estate of La Pointe Milou. This large villa has an oversize living, with a large bar and a gourmet kitchen. Most of the bedrooms of this villa are composed by suites. The heated pool is like the vi  …see more

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20

Lorient Vacation villa rental

Windward / Lorient

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Les Sables is a very nice villa extreamly well located on Lorient beach.It has a nice pool and offers a great privany.Perfect to go and see the turtles on the morning.BEDROOMView: Garden Equipment: air conditioning, fan, safe, bathroom with shower Be  …see more

from $391 / night

$2736 - $3816 / week

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from $391 / night

18

Mont Jean Vacation villa rental

Windward / Mont Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Les Amis Du Vent JAY A sweet sea of finesse and delicacy immediately submerges you when you enter for the first time into Villa Les Amis Du Vent. A magnificent garden literally leads into this sumptuous villa, adorned with white columns. The materials are noble na  …see more

from $2880 / night

$20160 / week

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from $2880 / night

24

Vacation home in Morne Criquet

Windward / Morne Criquet

4 4 Min stay varies

  • 4 bedrooms
  • Sleeps 4
  • Min stay varies
The entrance to Villa RGR leads you up a teak staircase to a manicured lawn, a wide teak deck and shimmering infinity pool, and the magnificent view from this home's vantage point high on the hillside of St. Jean. From here you can see the broad expanse of St. Jean  …see more

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(2) Very Good 

18

Windward / Pointe Milou

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

 …see more

from $566 / night

$3961 / week

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from $566 / night

10

Camaruche Vacation villa rental

Windward / Camaruche

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Marisa VEL in Camaruche, St Barts, has been totally renovated and is truly spectacular. Very comfortable with harmonious colors and antique furniture. An extremely private villa with many areas for sitting in the shade or in the sun. The extensive gardens have som  …see more

from $659 / night

$4608 / week

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from $659 / night

24

Morne Criquet Vacation home rental

Windward / Morne Criquet

5 5 Min stay varies

  • 5 bedrooms
  • Sleeps 5
  • Min stay varies
Located on the Camaruche hillside overlooking Lorient bay, Villa Avenstar (STR) offers its guests the ideal combination of elegant, modern design and a picture-perfect ocean view. From the hardwood terrace around the heated infinity pool and Jacuzzi, a broad vista of th  …see more

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20

Vacation villa in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Cocoland is located in one of the best spot of the island La Pointe Milou.This colonial style villa has a wonderful ocean view. The villa has a lot of assets like the ocean view, the sunset view, and a perfect privacy.A large deck with a pool is overlooking the ocean an  …see more

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24

Vacation 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 proximi  …see more

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14

Vacation villa in Windward

Windward / Marigot

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Kyody is located on the height of Marigot, overhang the lagoon of Grand Cul de Sac at few minutes from the beaches of Grand Cul de Sac and Marigot.Kyody is a very private and spacious villa.Our customers like in this villa the ocean view from almost all the rooms, the l  …see more

from $288 / night

$2016 - $4176 / week

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from $288 / night

9

Vacation villa in Marigot

Windward / Marigot

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Bougainvilliers is located hillside, at few steps from Marigot bay.This private villa has lovely views of Marigot Bay and the ocean.This two bedroom villa is perfect for a couple, or a family. The pool is surrounded by a terrace and the living room.Marigot Bay at a walk  …see more

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24

Vacation 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 furnish  …see more

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24

Vacation 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 conveniences  …see more

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20

Villa rental in Windward with swimming pool

Windward / Camaruche

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Belle Etoile AMS Close to Lorients shops and beach in Camaruche, this charming villa sits in a very convenient location. Sunset, the greatest show on Earth can be viewed from the covered dining area in the courtyard surrounded by lush tropical gardens. The wooden  …see more

from $308 / night

$2153 - $2873 / week

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from $308 / night

20

Villa rental in Camaruche

Windward / Camaruche

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Avenstar St Barts is made of five bedrooms, five bathrooms, and two pools. This amazing villa is located in the hillside of Camaruche and offers a stunning view over Lorient bay, St Maarten and the ocean. This newly built fully airconditionned villa has three leve  …see more

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20

Vacation villa rental

Windward / Lorient

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
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.BEDROOMView: Garden Equipmen  …see more

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15

Vacation 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 of Grand Cul de Sac, Petit Cul de Sac, and St. Martin. Nestled high on a hillside facing north, the views, the warm Caribbean ambience, the sun and re  …see more

from $594 / night

$4158 / week

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from $594 / night

20

Mont Jean Vacation villa rental

Windward / Mont Jean

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Nearest beach: Lorient, MarigotGustavia: 15 min.Restaurant: 10 min.Supermarket: 10 min.Airport: 10 min.CHILDREN AND PETSChildren min age:12 years oldPets: unauthorizedChildren on request.DETAILSThe Hillside villa has 4 bed  …see more

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