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Windward

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43 Holiday homes

Filters applied: Dishwasher (43)

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 £400 / night

£2400 - £9600 / week

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from £400 / night

20

Holiday villa with swimming pool in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Parsifal PAF is a small new villa in the Carenage area of Pointe Milou, a few steps from the Christopher Hotel. Th..  …see more

from £600 / night

£4200 - £6900 / week

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from £600 / night

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 - £5700 / week

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from £495 / night

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

from £274 / night

£1920 / week

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from £274 / 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

from £914 / night

£6400 / week

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from £914 / night

19

Holiday home in Windward

Windward / Morne Criquet

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Overlooking the bay of St. Jean, Villa Namaste (AUM) is spacious and comfortable with fabulous sunsets views. When you enter the house, on your right you find the large and open living area, nicely decorated with hardwood furniture and African art. The living room ov...  …see more

from £423 / night

£2960 / week

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from £423 / night

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 - £8100 / week

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from £729 / night

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 - £3360 / week

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from £378 / 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

from £486 / night

£3400 / week

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from £486 / 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

from £1714 / night

£12000 / week

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from £1714 / night

24

Holiday 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 t...  …see more

from £297 / night

£2080 / week

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from £297 / night

19

Holiday villa in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Villa Seaweed SEA The ideas of Le Corbusier, Scarpa, Barragan and Mies Van der Rohe gave birth to the very first modern,..  …see more

Pricing unknown

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Pricing unknown

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 - £9900 / week

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from £360 / night

10

Camaruche holiday 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 harm..  …see more

from £549 / night

£3840 - £6600 / week

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from £549 / 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 - £7200 / week

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from £643 / night

20

Holiday villa with swimming pool in Windward

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Caramba MBA is a delightful villa located at the end of Pt. Milou, with dramatic ocean views. It has been decorate..  …see more

from £669 / night

£4680 - £8400 / week

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from £669 / 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 - £5040 / week

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from £498 / night

16

Villa rental in Windward with swimming pool

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Mandarine Bleue LEA is one the real gems of Pointe Milou. From this villa, there is a 270 degree view and you will..  …see more

from £763 / night

£5340 - £9300 / week

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from £763 / night

20

Holiday villa in Windward

Windward / Lorient

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Air conditioning
  • 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

from £5929 / night

£41500 - £127600 / week

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from £5929 / night

20

Holiday villa with swimming pool in Windward

Windward / Camaruche

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 / week

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from £566 / night

15

Windward holiday villa rental

Windward / Mont Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 2 km
  • Child friendly
  • Air conditioning
The villa is located in Montjean, a quiet residential area, situated in the hillside overlooking the Caribbean Sea. From the villa's expansive terrace with its beautiful infinity pool, you can enjoy panoramic ocean views from sunrise to sunset.All rental rates are  …see more

from £755 / night

£5280 / week

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from £755 / night

10

Windward holiday villa rental

Windward / Pointe Milou

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 / week

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from £540 / night

18

Mont Jean holiday 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 ti..  …see more

from £2400 / night

£16800 - £33000 / week

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from £2400 / night

20

Villa rental in Windward with swimming pool

Windward / Camaruche

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 loc..  …see more

from £257 / night

£1794 / week

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from £257 / night

24

Holiday home rental

Windward / Morne Criquet

3 3 Min stay varies

  • 3 bedrooms
  • Sleeps 3
  • Min stay varies
With a wonderful panoramic view over St. Jean Bay, Villa Ker Anna (AKA) is a color-filled dream both inside and out. The blue Atlantic Ocean stretches off toward St. Maarten on the horizon, the green leaves of palm and gaiac sway in the breeze, and the interior of th...  …see more

from £480 / night

£3360 / week

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from £480 / night

15

Holiday 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..  …see more

from £643 / night

£4500 - £9900 / week

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from £643 / night

(2) Average 

7

Holiday villa in Marigot

Windward / Marigot

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Villa La Belle Vie LBV Built on a slope with high views over Marigot Bay, St Barts, to Pointe Milou and convenient acces..  …see more

from £420 / night

£2940 - £5880 / week

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from £420 / night

24

Holiday 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

from £972 / night

£6800 / week

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from £972 / night

24

Morne Criquet holiday 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...  …see more

from £1714 / night

£12000 / week

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from £1714 / night

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

from £366 / night

£2560 / week

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from £366 / night

13

Holiday villa rental

Windward / Pointe Milou

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • 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 / week

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from £412 / night

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

from £560 / night

£3920 / week

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from £560 / night

20

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 Cap Au Vent MOZ Located on a cliff at the very tip of Pointe Milou, St Barts chicest neighborhood, Villa Cap au Ve..  …see more

from £2550 / night

£17850 - £46500 / week

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from £2550 / night

16

Windward / Pointe Milou

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children

 …see more

from £343 / night

£2396 - £13165 / week

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from £343 / night

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

from £766 / night

£5360 / week

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from £766 / night

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

from £812 / night

£5680 / week

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from £812 / night

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

from £1074 / night

£7520 / week

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from £1074 / night

24

Holiday home in Windward

Windward / Vitet

3 3 Min stay varies

  • 3 bedrooms
  • Sleeps 3
  • Min stay varies
Villa (CLI) is located on the peak of Camaruche, St Barts, hillside with a view over Marigot, Cul de Sac and Mont Jean. A very open villa combining Asian, Chinese and African styles.The living area has a beautiful dark rattan weaved sofa with rich reddish brown over...  …see more

from £503 / night

£3520 / week

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from £503 / night

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

from £206 / night

£1440 / week

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from £206 / night

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 - £11700 / week

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from £840 / night

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