Villas in Windward: Rent luxury villas in Windward

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Windward

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45 Holiday homes

Filters applied: Air conditioning (45)

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 / week

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from £643 / 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 / week

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from £498 / 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 / week

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from £378 / 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 / week

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from £935 / 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 / week

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from £1500 / night

20

Holiday villa with swimming pool in Windward

Windward / Camaruche

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 - £5544 / 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

Pricing unknown

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Pricing unknown

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 / week

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from £669 / 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

 …see more

from £346 / night

£2416 / week

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from £346 / 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 / week

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from £549 / 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 / week

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from £729 / 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 / week

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from £986 / 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 / week

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from £360 / 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 / week

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from £1372 / 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

Pricing unknown

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Pricing unknown

33

Windward holiday villa rental

Windward / Pointe Milou

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • 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 £718 / night

£5928 / week

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from £718 / night

(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 £404 / night

£2420 - £6049 / week

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from £404 / 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 / week

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from £1200 / night

(2) Very Good 

18

Windward / Pointe Milou

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £464 / night

£3248 / week

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from £464 / night

10

Windward holiday villa rental

Windward / Pointe Milou

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 - £6120 / week

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from £540 / 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 / week

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from £495 / 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 / week

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from £2550 / 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 / week

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from £360 / 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 / week

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from £420 / night

13

Holiday villa rental

Windward / Pointe Milou

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 - £3480 / week

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from £412 / night

13

Windward / Vitet

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £574 / night

£4014 / week

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from £574 / 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 / week

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from £763 / 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 / week

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from £690 / 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 / week

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from £2400 / night

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 loc..  …see more

from £257 / night

£1794 - £2394 / week

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from £257 / 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. <br />Discounts may apply for 2 week bookings or longer  …see more

from £3643 / night

£25500 - £127000 / week

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from £3643 / 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 / week

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from £840 / night

20

Holiday villa with swimming pool in Windward

Windward / Camaruche

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 - £5280 / week

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from £489 / 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

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

15

Windward holiday villa rental

Windward / Mont Jean

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • 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.<br />All renta  …see more

from £761 / night

£5323 / week

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from £761 / night

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

Pricing unknown

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Pricing unknown

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

Pricing unknown

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Pricing unknown

20

Villa rental in Windward with swimming pool

Windward / Pointe Milou

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Festival BEN is a very private and spectacular villa situated on Pointe Milou. There is a infinity pool with large..  …see more

from £1158 / night

£8100 / week

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from £1158 / 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

Pricing unknown

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