Villas in Windward: Rent luxury villas in Windward

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Windward

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42 Holiday homes

Filters applied: Private pool (42)

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

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

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

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

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

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

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

33

Windward holiday villa rental

Windward / Pointe Milou

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
- Are you looking for a place where to celebrate your love for a special someone?- Are you the kind of person who want the best they can get, not for boasting, but for their own, private enjoyment?Then, let the magic of BelAmour help your couple create lifelong  …see more

from £669 / night

£4680 - £10945 / week

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from £669 / night

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

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

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

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

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

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

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

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

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

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 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

20

Mont Jean holiday villa rental

Windward / Mont Jean

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beverly BEV is an elegant and very private villa located on Mt. Jean, St Barts. This 4 bedroom villa offers privacy and..  …see more

from £1500 / night

£10500 - £16800 / week

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from £1500 / night

17

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 Cheyenne CHO sits on the Vitet hillside, commanding spectacular views of the east end of St Barts, including Grand..  …see more

from £729 / night

£5100 / week

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from £729 / 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

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

(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

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

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 / 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

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

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 - £27000 / week

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from £1543 / night

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 - £9480 / week

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from £738 / 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 - £10200 / week

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from £1012 / 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

20

Holiday villa with swimming pool in Camaruche

Windward / Camaruche

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Magnificently situated, Hill House BOW commands views of St Jean and beyond to St Martin. From the private terraces, the..  …see more

Pricing unknown

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Pricing unknown

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 islands. The  …see more

from £525 / night

£3670 - £11200 / week

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from £525 / night

20

Windward holiday villa rental

Windward / Pointe Milou

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • 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 / week

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from £2143 / night

20

Windward holiday villa rental

Windward / Vitet

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
There is a resident cat on this property.Villa Bibi BIB is perfection in every detail. Located high in Vitet, St Barts,..  …see more

from £1158 / night

£8100 - £17400 / week

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from £1158 / night

8

Holiday villa with swimming pool in Camaruche

Windward / Camaruche

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Kokono VKA is nestled in the hillside of Camaruche and offers a beautiful view over Lorient bay and the surroundin..  …see more

from £849 / night

£5940 - £12000 / week

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from £849 / night

20

Holiday villa with swimming pool in Windward

Windward / Camaruche

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
La Carette CAR is a very private and spectacular villa with a large pool and excellent views of Lorient, St Barts. Bedro..  …see more

from £489 / night

£3420 / week

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from £489 / night