List your home
Apply filters
£ to

237 Holiday homes in Windward

Reset search

Show results on map

Filter your search

Price per day

£ to

Bedrooms

Location

  • St. Barts Clear
  • Windward Clear
  • All towns
  • Anse de Lorient (10)
  • Camaruche (16)
  • Grand Cul de Sac (6)
  • Grand Fond (27)
  • Grande Saline (1)
  • Lorient (2)
  • Marigot (3)
  • Mont Jean (12)
  • Morne Criquet (34)
  • Petit Cul de Sac (86)
  • Petite Saline (2)
  • Pointe Milou (20)
  • Toiny (6)
  • Vitet (12)

more +

less -

Property type

more +

less -

Also consider

Filters applied: Non-Smoking property (237)

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
237 Results  |  
20 Photos

Villa | 7 Bedrooms | sleeps 14

7 Nights min stay

Add to shortlist

from £2674 /night

£18714 - £93568 / week

View

Key info:

  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • 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

19 Photos

Villa | 2 Bedrooms | sleeps 5

5 Nights min stay

Add to shortlist

from £515 /night

£3601 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Located on the hills of Vitet where it overlooks the Atlantic Ocean, Villa Kiara will seduce you at first glance with its very welcoming environment. 5 minutes drive from the beaches of Lorient and Marigot,  …see more

9 Photos

Villa | 1 Bedroom | sleeps 3

5 Nights min stay

Add to shortlist

from £280 /night

£1960 - £4320 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
This private Balinese-style villa is located Toiny on the "wild side" of St. Barth and after a small path that winds through the heart of high tropical grasses (5 minutes walk from the luxurious Le Toiny - Relay & Châteaux).  …see more

15 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £686 /night

£4800 - £16000 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
Main level : Infinity pool, Terrace, Living-room, Dining-room, Fully-equipped kitchen, Master bedroom #1, Ensuite bathroom with rain shower, Dressing-room, Master bedroom #2, Ensuite bathroom with rain shower, Dressing-room.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

6 Nights min stay

Add to shortlist

from £293 /night

£2047 - £2632 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Kiara, recently renovated, is an elegant 2 bedroom* villa located on the secluded neighbourhood of Vitet.  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £258 /night

£1805 - £5884 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • No pets allowed
  • Private garden
Villa Kermao is a fantastic 5 bedrooms / 4 bathrooms villa, with lots of charm, privacy and peacefulness.  …see more

21 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £230 /night

£1609 - £5848 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Located on the heights of Grand Cul de Sac, Villa Nilmath is a beautiful 2 bedroom villa with a gorgeous view over the lagoon of Grand Cul de Sac.  …see more

7 Photos

Villa | 4 Bedrooms | sleeps 8

6 Nights min stay

Add to shortlist

from £402 /night

£2808 - £14620 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Makasi offers a chic, secluded and serene retreat on St Barth.  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £627 /night

£4386 - £19503 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Hillside of Marigot, Villa Imagine is a luxurious and brand-new 3 bedroom villa with gorgeous sea views over the Grand Cul de Sac lagoon and its turquoise waters that you can enjoy from both inside and out.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 3

7 Nights min stay

Add to shortlist

from £154 /night

£1074 - £2866 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Villa Coral is a lovely 2 bedroom villa, ideal for a couple with a child.  …see more

23 Photos

Villa | 1 Bedroom | sleeps 2

7 Nights min stay

Add to shortlist

from £168 /night

£1170 - £2632 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Villa Ti Rêve, literally meaning "little dream", is a real haven of peace located in Grand Cul de Sac with undeniably everything to offer for a stylish, relaxing holiday.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

7 Nights min stay

Add to shortlist

from £1019 /night

£7132 - £24965 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Aureve is a gorgeous 4 bedroom villa is without a doubt a luxury villa that offers all the high end standards and much more.  …see more

15 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £508 /night

£3550 - £10234 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Located on the heights of Vitet, with a nice sea view, Villa Victoria is a sumptuous 2 bedroom villa offers contemporary design and a particularly neat decoration.  …see more

21 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £335 /night

£2340 - £11696 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
It features 3 large and private beautiful bedrooms, all with their own well-designed bathrooms  …see more

24 Photos

Villa | 3 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £410 /night

£2866 - £9240 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
Located on the heights of Pointe Milou, one of the most popular areas of St Barth, Villa Mandarine offers an amazing panoramic view on the sea toward Lorient and St Jean bays and the exceptional opportunity to enjoy both sunrise and sunset  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £402 /night

£2808 - £5556 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Le Magnifica is located in the heights of Vitet in the quiet and peaceful area of Devet. The villa has a beautiful 180 degree view of the ocean, Toiny Bay and Petit Cul de Sac.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £209 /night

£1462 - £4094 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Alta Vista is a very private 2 bedroom villa that offers stunning views of the ocean, lagoon and nearby islands.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £460 /night

£3217 - £10527 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Located within walking distance from Marigot Beach, Marigot Bay has 2 bedrooms.  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

Add to shortlist

from £318 /night

£2223 - £4620 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Villa Les Sables (CHL) indulges its guests with best of all worlds: a terrace just steps from the sea, green lawns and swaying palms, a refreshing pool, and classic Caribbean comfort. This property's charm and convenient Lorient location make it ideal for both couple...  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

Add to shortlist

from £752 /night

£5264 - £20468 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Bellevue is a 5 bedroom villa offering ocean views, 2 pools and a fitness room.  …see more

24 Photos

House | 6 Bedrooms | sleeps 6

5 Nights min stay

Add to shortlist

from £2089 /night

£14620 - £21053 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Crossing the threshold into Villa Good News (BMR) will seem to you like walking into another world. In this expansive, skylit space, standing on a gleaming white marble floor and surrounded by an exceptional collection of Beaux Arts antiques, you feel as if you've en...  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £569 /night

£3977 - £17544 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
La Rose des Vents (Villa LRV) offers a sensational view of the lagoon at Grand Cul de Sac. The white decor and open-air feel add to its ambiance. This home's recent renovation reflects the vibrant blue and green hues of the sea, an idyllic atmosphere for relaxation. ...  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £945 /night

£6609 - £17544 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
La Desirade is a 4 bedroom villa with views of all of Saint Jean Bay and is only a short walk to the beach.  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £2340 /night

£16375 - £73100 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Villa Anna is located on the hills of the private estate of Levant in Petit Cul-de-Sac in St Barths.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £402 /night

£2808 - £8188 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Bali is a 2 bedroom villa offering ocean and sunset views and a covered pool.  …see more

19 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £276 /night

£1930 - £4971 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Villa CHO commands spectacular views of St. Barth's eastern end from its vantage point high on a hillside in Vitet. From nearly every room in this house you can look out over the bays of Grand and Petit Cul de Sac and the open ocean beyond. The villa is painted and d...  …see more

20 Photos

Villa | 2 Bedrooms | sleeps 4

7 Nights min stay

Add to shortlist

from £298 /night

£2085 - £9357 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Villa Ted located in the beautiful surroundings of Dévé, has a stunning panoramic view of the over Grand Cul de Sac and the island of Tortue.  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

5 Nights min stay

Add to shortlist

from £836 /night

£5848 - £8480 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
La Belle Creole is a spacious 6 bedroom villa with a large pool facing the ocean view.  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £410 /night

£2866 - £10819 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
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

24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £669 /night

£4679 - £15790 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Soleil Levant is a 4 bedroom villa that offers views of the ocean from both sides, also providing views of both the sunrise and sunset.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 6

7 Nights min stay

Add to shortlist

from £485 /night

£3392 - £8772 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Villa Nita with its retro 60s décor is very stylish, has a superb view and a convenient central location in Lorient.  …see more

12 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £335 /night

£2340 - £5848 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Located in the heights of St. Jean overlooking both the Bay of St. Jean and Saline, Villa La Pêche (JJB) offers a traditional West Indies style with a wide-open view of lush green hills and brilliant blue sky and sea. The living area is furnished in wicker and vibran...  …see more

21 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

Add to shortlist

from £249 /night

£1737 - £2515 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Ideally located in Pointe Milou, facing St. Barth's windward side, Turtle Island, and the Atlantic Ocean, Villa Bonbonniere is sunlit and breezy. The villa's open and airy living room features large and comfortable off-white sofas facing the terrace, the pool and the...  …see more

24 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £786 /night

£5498 - £16901 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
With its main living area open on three sides to the sun and breezes and panoramic view, Villa Blue Heaven (FUN) envelops you in the essence of St. Barth living. Decorated in classic West Indies blue and white, this is the iconic island home. The layout of this spaci...  …see more

22 Photos

House | 4 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £502 /night

£3509 - £11404 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Villa Bord de Mer (BDM) is an elegant, West Indies style villa surrounded by lush tropical flora, just a one-minute stroll via its own private path to the beautiful, white-sand beach of St Jean. The spacious interior is decorated with dark wood antiques and light fab...  …see more

18 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

Add to shortlist

from £268 /night

£1872 - £3860 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Located above Lorient Bay and offering a dramatic view over the ocean and the surrounding islands, Villa Tortue (TOR) pampers its guests with contemporary design and elegant furnishings. The integrated living area and bedroom open onto the bright terrace, inviting in...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £836 /night

£5848 - £19503 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
The aptly named Villa Imagine looks out over a wide expanse of tropical sea and sky from near the crest of the hill over Marigot. This delightful home offers a rare blend of simplicity and style, with a layout that makes the most of a great location and tasteful furn...  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £351 /night

£2457 - £8129 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
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

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £234 /night

£1638 - £7544 / week

View

Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Kyody is a very private 2 bedroom villa with large living area and an astonishing ocean view.  …see more

20 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

Add to shortlist

from £101 /night

£702 - £1433 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Villa SJA's unique situation creates a rare opportunity for those looking for the ultimate in convenience. Just yards away from a white-sand beach, and easy walking distance from the supermarkets and bakery in Lorient, this home allows you to spend your days the way ...  …see more

22 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £460 /night

£3217 - £9357 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Villa Ever Sail (BOT) is a delightful modern villa sitting high above Grand Cul de Sac, with superb ocean views. The craftsmanship and the extensive use of teak along with the furnishings lend a unique nautical feel to this villa. In design and style, this home manag...  …see more

22 Photos

House | 1 Bedroom | sleeps 1

5 Nights min stay

Add to shortlist

from £205 /night

£1433 - £3158 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
St. Barth's remote and unspoiled Toiny Bay is best known to surfers and the island's more intrepid visitors. The newly constructed Villa Casamia (TTM) is perfectly suited to this pristine region: a secluded oasis with a spirit perfectly in harmony with the beauty of ...  …see more

24 Photos

Villa | 5 Bedrooms | sleeps 10

7 Nights min stay

Add to shortlist

from £3342 /night

£23392 - £61404 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Indian Song is a 5 bedroom villa with ocean views and tennis and beach nearby.  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £485 /night

£3392 - £14036 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
Mapou is a 2 bedroom villa with ocean views.  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

Add to shortlist

from £410 /night

£2866 - £7603 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Perched high on Colombier hillside, Villa Grain de Folie (GDF) offers a splendid view over Gustavia, the islands of Saba and St. Eustatius, and brilliant Caribbean sunsets. The villa is tastefully decorated in a contemporary style. From the living room and the kitche...  …see more

24 Photos

House | 5 Bedrooms | sleeps 5

5 Nights min stay

Add to shortlist

from £853 /night

£5965 - £22574 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Remarkably open and airy, Villa Vina (VNA) is composed of separate cottages in a marvelously landscaped and natural garden. With a living an dining area completely open on three sides and perfectly integrated with the outdoor space, terrace and pool, this villa is ma...  …see more

24 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

Add to shortlist

from £376 /night

£2632 - £9357 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
C'est La Vue is a 2 bedroom villa that offers beautiful ocean and sunset views.  …see more

24 Photos

House | 2 Bedrooms | sleeps 2

5 Nights min stay

Add to shortlist

from £376 /night

£2632 - £9357 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
High in the hills of Vitet, Villa Au Coeur du Rocher (ACR) offers the kind of simple sophistication that can make a St. Barth vacation comfortable, relaxing and carefree. With a magnificent view over the surrounding landscape and the wide Atlantic, this newly built p...  …see more

24 Photos

Villa | 4 Bedrooms | sleeps 8

5 Nights min stay

Add to shortlist

from £744 /night

£5205 - £17486 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
25% off the month of June 2014 Black Pearl is located on the hillside of Marigot and overlooks the lagoon of Grand Cul de Sac and the ocean. The view is astonishing.  …see more

24 Photos

House | 3 Bedrooms | sleeps 3

5 Nights min stay

Add to shortlist

from £460 /night

£3217 - £3802 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Splashes of color in the Asian-inspired decor and artworks enliven the serene atmosphere at Casa Zenial (Villa KAS). From its rare Saline location, Villa KAS looks out over swaying palm fronds at the valley of Grand Saline, the dunes beside the beach, and the blue Ca...  …see more