Villas in Windward: Rent luxury villas in Windward

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Windward

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37 Holiday homes

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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 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

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

13

Windward / Vitet

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £569 / night

£3982 - £18752 / week

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from £569 / 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

(2) Very Good 

18

Windward / Pointe Milou

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £460 / night

£3222 - £13165 / week

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from £460 / 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

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

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

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 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 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 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

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

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

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

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

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

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

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

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

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 £343 / night

£2396 - £13165 / week

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from £343 / 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

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

20

Holiday villa rental

Windward / Pointe Milou

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Villa Samsara AMA Situated high above the ocean, with a panoramic western view in Pointe Milou, St. Barth is the spectac..  …see more

from £463 / night

£3240 / week

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from £463 / 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

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

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

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 - £11400 / week

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from £1158 / 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

from £3858 / night

£27000 / week

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from £3858 / night

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