Villas in Windward: Rent luxury villas in Windward

Close

View larger map

Price per night

Price per night

to

Bedrooms

Bathrooms

Location

  • Caribbean
  • St. Barts
  • Windward

Location

  • All locations
  • Camaruche (6)
  • Lorient (6)
  • Marigot (2)
  • Mont Jean (6)
  • Pointe Milou (19)
  • Vitet (7)

More

Less

Property type

More

Less

Also consider

Pointe Milou
42 properties
Vitet
30 properties
Morne Criquet
26 properties
Marigot
18 properties
Gites Lorient
14 properties
Mont Jean
12 properties
Anse de Lorient
10 properties
Camaruche
10 properties
Petite Saline
7 properties
Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

46 Holiday homes

Filters applied: Air conditioning (46)

1 / 5

Windward / Pointe Milou

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £382 / night

£2291 - £9161 / week

Book Book View

from £382 / night

1 / 18

188-Les Amis du Vent - Mont Jean villa sleeps 6

Windward / Mont Jean

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Les Amis Du Vent JAY A sweet sea of finesse and delicacy immediately submerges you when you enter for the first time into Villa Les Amis Du Vent. A magnificent garden literally leads into this sumptuous villa, adorned with white columns. The materials are noble na  …see more

from £2400 / night

£16800 - £33000 / week

Enquire Enquire View

from £2400 / night

1 / 13

Windward / Vitet

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Ask owner if suitable for children; Car essential;
 …see more

from £543 / night

£3800 - £17894 / week

Book Book View

from £543 / night

1 / 13

318-Safari - Pointe Milou villa sleeps 2

Windward / Pointe Milou

1 bedroomSleeps 27 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Perched above the ocean with panoramic views of the bays of Lorient, St. Jean, Anse des Cayes, and St. Maarten, sits Villa Safari ARI. This magnificent onebedroom villa located in Pointe Milou is on the north side of the island facing to the west.To create a warm atmosp  …see more

from £412 / night

£2880 / week

Enquire Enquire View

from £412 / night

1 / 20

69-Eden House - Marigot villa sleeps 6

Windward / Marigot

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car essential; Air conditioning;
Villa Eden House GRO Eden House was one of the very first villas on the island. It has now become one of the finest contemporary achievements of the island. It also boasts an exceptional location with a path directly accessing the sea and double exposure both to Marigot  …see more

from £1372 / night

£9600 - £20010 / week

Enquire Enquire View

from £1372 / night

1 / 17

115-Les Mouettes - Vitet villa sleeps 6

Windward / Vitet

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Les Mouttes PAY is a charming villa with heated pool, located in a private area in Vitet. With all of the rooms are under the same roof, it is a perfect family house.The spacious master bedroom is located on the first floor, with the other 2 small bedrooms located  …see more

from £360 / night

£2520 - £4200 / week

Enquire Enquire View

from £360 / night

1 / 20

51-La Danse Des Etoiles - Pointe Milou villa sleeps 6

Windward / Pointe Milou

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
At first glance the alchemy of raw materials, mineral rock and rigorous concrete are palpable as they harmonize with the warmth and the nobility of wood and give birth to this unique and spectacular villa located in Pointe Milou. It took nearly two years for a team of s  …see more

from £6429 / night

£45000 / week

Enquire Enquire View

from £6429 / night

1 / 13

130-Indigo Orchid - Lorient villa sleeps 2

Windward / Lorient

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Indigo Orchid TOR is a newly built and charming one bedroom villa in Lorient, St Barts that can be rented individually or can be combined with its neighbor villa, La Carette to make a total of 3 bedrooms. When rented separately, both villas maintain complete priva  …see more

from £360 / night

£2520 - £9900 / week

Enquire Enquire View

from £360 / night

1 / 15

316-Anais - Vitet villa sleeps 6

Windward / Vitet

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
The beautiful Villa Anais AIA in Vitet, at the center of the eastern half of St. Barts, offers guests spectacular views of Grand Cul de Sac, Petit Cul de Sac, and St. Martin. Nestled high on a hillside facing north, the views, the warm Caribbean ambience, the sun and re  …see more

from £495 / night

£3465 - £5700 / week

Enquire Enquire View

from £495 / night

1 / 20

114-La Vue Panoramique - Mont Jean villa sleeps 4

Windward / Mont Jean

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
La Vue Panoramique PAT Located on exclusive Mont Jean, this villa enjoys 300 degree breathtaking views. Sint. Maarten, Anguilla, Marigot Bay and Grand Cul de Sac are included in the sight. The large black bottom overflow pool, heated during the winter season, as well as  …see more

from £935 / night

£6540 - £12000 / week

Enquire Enquire View

from £935 / night

1 / 15

122-Raia - Lorient villa sleeps 4

Windward / Lorient

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Raia RIA is located directly on Lorient Beach, one can hear the sound of the waves lapping against the shore. The beach is quite calm and there are constant breezes. With mosquito netting in both bedrooms, it is possible to sleep with just the breezes. This villa  …see more

from £643 / night

£4500 - £9900 / week

Enquire Enquire View

from £643 / night

1 / 20

324-Belle Etoile - Camaruche villa sleeps 4

Windward / Camaruche

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Belle Etoile AMS Close to Lorients shops and beach in Camaruche, this charming villa sits in a very convenient location. Sunset, the greatest show on Earth can be viewed from the covered dining area in the courtyard surrounded by lush tropical gardens. The wooden  …see more

from £257 / night

£1794 / week

Enquire Enquire View

from £257 / night

1 / 15

153-Adore - Lorient villa sleeps 4

Windward / Lorient

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Great for children of all ages ; Car essential; Air conditioning;
Villa Adore ADR is simple beachfront villa under one roof in Lorient, St Barts. There is a great yard and easy access to the beach. There is a combination livingdining area with a counter separating the kitchen from the living room. The bedrooms are located off living a  …see more

from £378 / night

£2640 - £3360 / week

Enquire Enquire View

from £378 / night

1 / 20

82-Milou - Pointe Milou villa sleeps 4

Windward / Pointe Milou

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Milou KID, located in Pointe Milou, has two bedrooms, two bathrooms and a pool. Stone steps lead to the villa that opens to a large living and dining area facing a spectacular view over the ocean and the surrounding islands. On the main level, to the left, a large  …see more

from £729 / night

£5100 - £8100 / week

Enquire Enquire View

from £729 / night

1 / 17

45-Cheyenne - Vitet villa sleeps 6

Windward / Vitet

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Cheyenne CHO sits on the Vitet hillside, commanding spectacular views of the east end of St Barts, including Grand Petit Cul de Sac and the open ocean beyond. The villa is painted in a very soft pastel pink stucco. Openair hallways and numerous tropical plantings  …see more

from £729 / night

£5100 / week

Enquire Enquire View

from £729 / night

1 / 20

29-Beverly - Mont Jean villa sleeps 8

Windward / Mont Jean

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Beverly BEV is an elegant and very private villa located on Mt. Jean, St Barts. This 4 bedroom villa offers privacy and an amazing view of the ocean, and the surrounding islands, with magnificent sunsets in the summer time. Mainly built on one level except steps leading  …see more

from £1500 / night

£10500 - £16800 / week

Enquire Enquire View

from £1500 / night

1 / 20

100-Caramba - Pointe Milou villa sleeps 4

Windward / Pointe Milou

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Caramba MBA is a delightful villa located at the end of Pt. Milou, with dramatic ocean views. It has been decorated with a wonderful use of both overstuffed wicker with white fabrics and mahogany beds with crisp white fabrics. The rooms are very bright and airy wi  …see more

from £669 / night

£4680 - £8400 / week

Enquire Enquire View

from £669 / night

1 / 8

162-Sea Breeze - Lorient villa sleeps 4

Windward / Lorient

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Sea Breeze EZE is a very quiet and peaceful Lorient, St Barts, villa with beautiful palms, the sounds of water lapping and St. Martin in the distance. It is only a few meters from Lorient Beach. There is an indoor and outdoor dining and a nice deck on two levels with a  …see more

from £498 / night

£3480 - £5040 / week

Enquire Enquire View

from £498 / night

1 / 20

227-Cap Au Vent - Pointe Milou villa sleeps 8

Windward / Pointe Milou

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Cap Au Vent MOZ Located on a cliff at the very tip of Pointe Milou, St Barts chicest neighborhood, Villa Cap au Vent MOZ is truly one of the most deluxe and extraordinary villas on St. Barts. Totally private, surrounded by the ocean and its breezes, Villa Cap au V  …see more

from £2550 / night

£17850 - £46500 / week

Enquire Enquire View

from £2550 / night

1 / 17

48-La Corniche - Pointe Milou villa sleeps 6

Windward / Pointe Milou

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
La Corniche DAY is located 150 feet above the water at the tip of Pointe Milou, St Barts, with panoramic views all the way to St. Martin. This breathtaking villa has large rooms with privacy and charm and provides both sunrise and sunset vistas. There are two bedrooms o  …see more

from £1200 / night

£8400 - £10200 / week

Enquire Enquire View

from £1200 / night

1 / 10

132-Marisa - Camaruche villa sleeps 4

Windward / Camaruche

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Marisa VEL in Camaruche, St Barts, has been totally renovated and is truly spectacular. Very comfortable with harmonious colors and antique furniture. An extremely private villa with many areas for sitting in the shade or in the sun. The extensive gardens have som  …see more

from £549 / night

£3840 - £6600 / week

Enquire Enquire View

from £549 / night

1 / 20

96-Kaiteki - Camaruche villa sleeps 6

Windward / Camaruche

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Kaiteki LUZ was built with privacy and relaxation in mind. Perfect for families and large groups, it is built on three different levels with views over beautiful Lorient Bay. The main terrace includes a covered outdoor living area, the primary dining area, as well  …see more

from £566 / night

£3960 / week

Enquire Enquire View

from £566 / night

(2) Good 

1 / 7

190-La Belle Vie - Marigot villa sleeps 6

Windward / Marigot

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Great for children of all ages ; Car essential; Air conditioning;
Villa La Belle Vie LBV Built on a slope with high views over Marigot Bay, St Barts, to Pointe Milou and convenient access to the island road, Lake Bay is a NEW 3 bedroom2 bathroom villa located in Marigot with a pool and terrace overlooking Marigot bay. Loft like rooms  …see more

from £420 / night

£2940 - £5880 / week

Enquire Enquire View

from £420 / night

1 / 10

50-Hidden Treasures - Pointe Milou villa sleeps 4

Windward / Pointe Milou

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
Hidden Treasures DKD The setting of this villa so captures your fantasy of a tropical island paradise that Hollywood could not have done better. Located in prestigious Pointe Milou, St Barts, newly renovated Villa Hidden Treasures is a tiny jewel that offers qualities r  …see more

from £540 / night

£3780 / week

Enquire Enquire View

from £540 / night

1 / 20

La Plage - Lorient villa sleeps 14

Windward / Lorient

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Great for children of all ages ; Air conditioning; No pets allowed;
Villa La Plage is an architectural gem designed by Patrick Benaben to capture the romance of the perfect seaside location. Guests at aptly named La Plage (the Beach) will enjoy sweeping views of the Caribbean Sea. A curved swimming pool echoes the curve of the horizon,  …see more

from £3215 / night

£22500 - £112500 / week

Book Book View

from £3215 / night

1 / 9

53-Villa Pastel - Vitet villa sleeps 6

Windward / Vitet

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Pastel EBA is a little gem, situated in the Vitet countryside with pastoral and ocean views. Simplistic in style, the villa has been constructed using modern materials such as wood, polished concrete, steel and glass, while at the same time keeping a traditional i  …see more

from £986 / night

£6900 - £13200 / week

Enquire Enquire View

from £986 / night

1 / 16

87-Mandarine Bleue - Pointe Milou villa sleeps 4

Windward / Pointe Milou

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Mandarine Bleue LEA is one the real gems of Pointe Milou. From this villa, there is a 270 degree view and you will enjoy both sunrise and sunset. The villa is gaily decorated in blue and white and is extremely comfortable. Each bedroom is situated for privacy and  …see more

from £763 / night

£5340 - £9300 / week

Enquire Enquire View

from £763 / night

1 / 16

78-Jane - Pointe Milou villa sleeps 8

Windward / Pointe Milou

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Jane JMS is a unique hideaway perched in complete privacy on a beautiful hillside in Pointe Milou, St Barts. The villas look is sophisticated, yet casual glamorous and easy calming and serene. Come to Villa Jane and prepare to do absolutely nothing, with one of th  …see more

from £690 / night

£4830 - £10500 / week

Enquire Enquire View

from £690 / night

1 / 15

Villa 3 bedrooms St Barts Montjean Pool Jacuzzi

Windward / Mont Jean

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 2 km; Great for children of all ages ; Air conditioning;
The villa measures 2691 ft2 interior surface and 1.2 acresTotal surface on a private and gated propertyEntrance to the property only with an entry codeThe villa is composed of two separate buildingsLarge outside space with covered patios and open terracesBreathtaking vi  …see more

from £720 / night

£5039 / week

Book Book View

from £720 / night

(2) Very Good 

1 / 18

Windward / Pointe Milou

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Ask owner if suitable for children; Car essential;
 …see more

from £439 / night

£3075 - £12562 / week

Book Book View

from £439 / night

1 / 33

BelAmour, a St. Barths Luxury Villa for Lovers

Windward / Pointe Milou

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Air conditioning;
- 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 memories  …see more

from £649 / night

£4537 - £10611 / week

Book Book View

from £649 / night

1 / 15

52-LAbricotier - Pointe Milou villa sleeps 4

Windward / Pointe Milou

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa LAbricotier DOR is located in Pointe Milou, St Barts, with a spectacular view of the ocean. This villa is tastefully decorated in shades of periwinkle blue, beige and off white. As you enter in the front door you have a large, wideopen space, which splits, as a li  …see more

from £738 / night

£5160 - £9480 / week

Enquire Enquire View

from £738 / night

1 / 20

35-Hill House - Camaruche villa sleeps 8

Windward / Camaruche

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Magnificently situated, Hill House BOW commands views of St Jean and beyond to St Martin. From the private terraces, the private guest cottages and luxurious master suite, are incredible panoramic views. At the center of this beautiful property is a vast infinity pool a  …see more

from £1286 / night

£9000 / week

Enquire Enquire View

from £1286 / night

1 / 20

113-Elevation - Mont Jean villa sleeps 6

Windward / Mont Jean

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Charming and private, Villa SIB PAR is located on the Mont Jean hillside, St Barts. The villa has 3 bedrooms and can be combined with a separate cottage at the entrance of the property.The villa is built mainly on one level and has views in both directions, toward Point  …see more

from £1543 / night

£10800 - £27000 / week

Enquire Enquire View

from £1543 / night

1 / 19

312-Abby - Vitet villa sleeps 6

Windward / Vitet

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Abby ABB is a very private and sensational villa set high in Vitet, St Barts. Abby offers guests some of St. Barths most dramatic sea views, including the islands of Tortue, Toc Vert, Fregate and Anguilla, as well as the Bay of Marigot. Petit and Grand Cul de Sac  …see more

from £840 / night

£5880 - £11700 / week

Enquire Enquire View

from £840 / night

1 / 20

321-Samsara - Pointe Milou villa sleeps 4

Windward / Pointe Milou

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Great for children of all ages ; Car essential; Air conditioning;
Villa Samsara AMA Situated high above the ocean, with a panoramic western view in Pointe Milou, St. Barth is the spectacular villa Samsara Villa AMA. Located in a superb spot to watch unparalleled sunsets, the warm ambience created by honeycolored Java teak sets the th  …see more

from £463 / night

£3240 / week

Enquire Enquire View

from £463 / night

1 / 18

Villa Tranquille - Vitet villa sleeps 6

Windward / Vitet

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £272 / night

£1900 - £9800 / week

Book Book View

from £272 / night

1 / 8

135-Kokono - Camaruche villa sleeps 6

Windward / Camaruche

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Villa Kokono VKA is nestled in the hillside of Camaruche and offers a beautiful view over Lorient bay and the surroundings islands. It features beautiful sunsets year round. Road noise can be heard due to proximity of the road.Recently built, this new villa is lovely. I  …see more

from £849 / night

£5940 - £12000 / week

Enquire Enquire View

from £849 / night

1 / 20

340-La Banane - Lorient villa sleeps 18

Windward / Lorient

9 bedroomsSleeps 18Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
Banane BAN A secret estate, a confidential address, a unique intimate atmosphere. A privileged place where you unpack your suitcase with a deepset feeling of having found the right place. An exceptional hideout where you come to lose yourself, the better to find yoursel  …see more

from £5572 / night

£39000 / week

Enquire Enquire View

from £5572 / night

1 / 20

39-La Carette - Camaruche villa sleeps 4

Windward / Camaruche

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
La Carette CAR is a very private and spectacular villa with a large pool and excellent views of Lorient, St Barts. Bedrooms are located in a separate bungalow. They are both large with king beds, ceiling fans and air conditioning. Each opens up onto a terrace and there  …see more

from £489 / night

£3420 / week

Enquire Enquire View

from £489 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page