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Windward

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53 Holiday homes

Filters applied: DVD player (53)

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 £394 / night

£2363 - £9449 / week

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from £394 / 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

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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17

Vitet holiday villa rental

Windward / Vitet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Les Mouttes PAY is a charming villa with heated pool, located in a private area in Vitet. With all of the rooms ar..  …see more

from £360 / night

£2520 - £4200 / week

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from £360 / 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 £270 / night

£1890 / week

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from £270 / 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 £293 / night

£2048 / week

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from £293 / 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 - £9900 / week

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from £360 / 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 - £13200 / week

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from £986 / night

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 - £4200 / week

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from £309 / 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

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 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

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

(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 - £3480 / week

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from £369 / 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

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

17

Holiday villa with swimming pool in Pointe Milou

Windward / Pointe Milou

3 6 Min stay varies

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

from £1200 / night

£8400 - £10200 / week

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from £1200 / 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

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

from £158 / night

£1103 / week

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from £158 / night

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

from £214 / night

£1497 / week

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from £214 / 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

20

Holiday villa in Windward

Windward / Pointe Milou

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
At first glance the alchemy of raw materials, mineral rock and rigorous concrete are palpable as they harmonize with the..  …see more

from £6429 / night

£45000 / week

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from £6429 / 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 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 £473 / night

£3308 / week

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from £473 / night

20

Holiday villa rental

Windward / Mont Jean

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
La Vue Panoramique PAT Located on exclusive Mont Jean, this villa enjoys 300 degree breathtaking views. Sint. Maarten, A..  …see more

from £935 / night

£6540 - £12000 / week

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from £935 / 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

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 £1687 / night

£11812 / week

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from £1687 / 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

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 Eden House GRO Eden House was one of the very first villas on the island. It has now become one of the finest cont..  …see more

from £1372 / night

£9600 - £20010 / week

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from £1372 / 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 £956 / night

£6693 / week

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from £956 / 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

Holiday home in Windward

Windward / Morne Criquet

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
Villa On the Rocks (JIM) welcomes its guests with a delightful combination of smart design, quality furnishings, and a picture-perfect view. You enter the property onto a secluded hardwood deck bordered by cashew and palm trees, a vantage point overlooking the blue w...  …see more

from £2025 / night

£14174 / week

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from £2025 / night

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 - £10500 / week

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from £690 / night

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

from £5572 / night

£39000 / week

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from £5572 / 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 £338 / night

£2359 - £12958 / week

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from £338 / 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 £552 / night

£3859 / week

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from £552 / night

9

Holiday villa in Pointe Milou

Windward / Pointe Milou

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
St Barts Villa Le Reve Realise SFO is a beautiful villa located in Pointe Milou, St Barts. This villa is equipped with e..  …see more

from £2915 / night

£20400 / week

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from £2915 / 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 £799 / night

£5591 / week

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from £799 / night

14

Holiday villa in Vitet

Windward / Vitet

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Casa Nomada NOM is a charming villa located in Vitet with 2 bedrooms, 2 bathrooms and a pool. This villa offers a partia..  …see more

from £438 / night

£3060 - £5700 / week

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from £438 / 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 £203 / night

£1418 / week

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from £203 / night