50 Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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2,666 Vacation rentals

13

Colombier Vacation villa rental

St. Barts / Colombier

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
South View is located on the heights of Colombier. The villa facing the sun offers a maximum of sunlight, and a beautiful sunset view. The villa is conveniently located a few minutes from Gustavia, its shops and restaurants and the beautiful beach of Flamands. A large  …see more

from $1089 / night

$7620 / week

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from $1089 / night

24

St. Barts / Colombier

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

 …see more

from $321 / night

$1815 - $4696 / week

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from $321 / night

12

Vacation villa in Leeward

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Ostra Strandgatan is an recently renovated apartment It is located at the entrance of the Gustavia harbour. The flat has an ocean view on the harbour entrance, and the ocean view toward the sunsetThe flat is fully air conditioned. It offer a large living room, a dining  …see more

from $759 / night

$5308 / week

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from $759 / night

8

Villa rental in Corossol

St. Barts / Corossol

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Lottie LOT is a delightful European loft style apartment located across from the beach in Corossol, St Barts.Upon entering this fully airconditioned apartment there is a large room with a 4 person jacuzzi which looks out over the beach, and a living area with a wh  …see more

from $381 / night

$2667 - $4953 / week

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from $381 / night

15

Vacation villa in Leeward

St. Barts / Colombier

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
La Baleine BAL which means Whale in English was named after a group of rocks in the ocean below and after the whales that are sometimes spotted from the villa on their yearly migratory travels. A charming villa located high in the hills of Colombier with breathtaking vi  …see more

from $665 / night

$4649 - $6211 / week

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from $665 / night

17

St. Jean / St. Jean Beach

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

 …see more

from $516 / night

$3614 - $5680 / week

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from $516 / night

14

Vacation villa in Leeward

St. Barts / Colombier

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
Villa South View SVV is a 2 bedroom, 2 bathroom villa, perched on Colombier hillside and offering a splendid view over Gustavia, the island of Saba and St Eustatius, as well as gorgeous sunsets. Just a few minutes from Gustavia, its shops and restaurants and the beauti  …see more

from $490 / night

$3429 / week

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from $490 / night

5

Vacation villa in Anse des Flamands

Anse des Flamands / Flamands Beach

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Villa Polaris ALB is located on Flamands Beach on the northwest end of the island. Under one roof, this cozy villa features an open plan living room and kitchen opening on to a covered outdoor dining area. A wooden deck with teak lounge chairs offers comfortable seating  …see more

from $409 / night

$2858 - $3810 / week

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from $409 / night

15

Villa rental in Anse des Flamands

St. Barts / Anse des Flamands

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Two of the nicest beaches of Saint Barth, Flamands and Colombier, within a walking distance from the villa The villa Ushuaia is located in Flamands close to La Petite Anse bay.This spacious and very private villa overhangs the ocean and the cliffs of Colombier.We lik  …see more

from $2722 / night

$19050 / week

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from $2722 / night

12

St. Barts / Anse des Cayes

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $207 / night

$1447 - $3512 / week

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from $207 / night

18

Vacation villa in Gustavia

St. Barts / Gustavia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Villa Lam is not for everybody just for the city life addictsOverhanging Gustavia harbour, Lam is a chic and contemporary 3 bedroom villa.The ocean view on the traffic of the harbour and the sunset is absolutely gorgeous.This perfect location above Gustavia harbour al  …see more

Pricing unknown

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Pricing unknown

12

Leeward Vacation villa rental

St. Barts / Colombier

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Perched above Flamands beach,villa Leana FLO is a one bedroom, one bathroom villa with infinity pool. This newly built villa is located on the hillside of Colombier, St Barts, and offers a splendid view over Flamands bay and Bonhomme Island.The villa is made up of three  …see more

from $485 / night

$3391 - $4839 / week

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from $485 / night

20

Corossol Vacation villa rental

St. Barts / Corossol

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Habitation Saint Louis HSL is located on the hillside above the charming village of Corossol.Private and quiet, this villa offers you sunsets and a sea views of Corrosol and Gustavia Harbour entrance.This villa is built on two levels and offers private and direct access  …see more

from $1198 / night

$8382 - $17145 / week

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from $1198 / night

20

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $429 / night

$2996 - $7229 / week

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from $429 / night

(1) Excellent 

11

Leeward Vacation villa rental

St. Barts / Anse des Flamands

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
Apsara is a nice villa rental situated in Flamands in Saint Barthelemy in the French CaribbeanThis new house is made of two bedrooms, two bathrooms, a kitchen and a living room opened onto the terrace, the pool and the view.Thanks to the bedrooms in two separate bungalo  …see more

from $980 / night

$6858 / week

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from $980 / night

15

Home rental in Gustavia with swimming pool

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Located on glitzy St. Barthélemy, this modern house offers the perfect base for exploring the everything the island has to offer. It can easily accommodate 4 sun-loving holidaymakers. Set just 100 metres from the sea and 500 metres from local shops, sights and restau  …see more

from $622 / night

$3775 - $10128 / week

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from $622 / night

(1) Excellent 

20

Vacation villa in Leeward

St. Barts / St. Jean

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Villa Sous la Falaise SOU is nestled just above the water at the eastern end of St. Jean Beach, St Barts. Separate cottages offer a superb view of the beach and the Eden Rock Hotel. A stone path connects the individual bedroom cottages to the main living, dining and kit  …see more

from $1067 / night

$7468 / week

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from $1067 / night

(1) Excellent 

10

Vacation villa in Leeward

St. Barts / Anse des Flamands

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
Les Raisiniers is a small cottage located on Flamands beach.Flamands beach is the largest beach of the island. This beach has few beach front restaurants. In front of the villa, a tropical garden with coconuts has a wicket which gives access to this white sandy beach.  …see more

from $333 / night

$2325 / week

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from $333 / night

24

Vacation villa with swimming pool in Leeward

Anse des Flamands / Flamands Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Welcome to Villa Micela, a gorgeous two bedroom beach front villa in St Barths located directly on Flamands Beach. Wake up to the wonderful sea breezes. Bask in near perfect weather literally steps from one of the nicest beaches in St Barths.Flamands Beach is on  …see more

from $1071 / night

$7501 - $22001 / week

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from $1071 / night

6

Vacation villa rental

St. Barts / Gustavia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
Nearest beach Shell BeachGustavia 2 min. Restaurant 5 min. Supermarket 10 min. Airport 2 min.GUSTAVIA, ST BARTSNearest beach: Shell BeachGustavia: 2 min.Restaurant: 5 min.Supermarket: 10 min.Airport: 2 min.CHILDREN AND PETSChildre  …see more

from $408 / night

$2850 / week

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from $408 / night

13

Vacation villa in Corossol

St. Barts / Corossol

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Petit Saint Louis PSL is a very charming Caribbeanstyle bungalow located on the hillside of Corossol, St Barts. You will enjoy the sea view of Corossol harbor and the beautiful sunset.This cottage is surrounded by lovely gardens. It has a Master bedroom with ensuite bat  …see more

from $381 / night

$2667 - $17145 / week

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from $381 / night

12

Vacation villa in Anse des Flamands

St. Barts / Anse des Flamands

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Roc Flamands 5 is located on the heights of Flamands in the private community of Roc Flamands. The villa is built on two flors The bedrooms floors are looking on decks or the pool. The living floor surrounded by a terrace is looking on the ocean view . The villa is onl  …see more

from $817 / night

$5715 / week

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from $817 / night

11

Leeward Vacation home rental

St. Barts / Corossol

1 1 Min stay varies

  • 1 bedroom
  • Sleeps 1
  • Min stay varies
Petit Saint Louis (PSL) is a very charming Caribbean-style bungalow located on the hillside of Corossol, St Barts. You will enjoy the sea view of Corossol harbor and the beautiful sunset.This cottage is surrounded by lovely gardens. It has a Master bedroom with ensu  …see more

from $357 / night

$2501 / week

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from $357 / night

20

Leeward Vacation villa accommodation

St. Barts / Anse des Flamands

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa HBV is the perfect place for lovers of all ages. Nestled into the Flamands, St Barts, hillside, but with a level entry and comfortable one floor living, Villa HBV was recently renovated to include two separate and private bedroom bungalows. The very large master b  …see more

from $654 / night

$4572 - $8230 / week

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from $654 / night

15

Anse des Flamands Vacation villa rental

St. Barts / Anse des Flamands

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
Art is well located in Flamands within a walking distance from the beach. The villa has a beautiful ocean view.The villa has 2 floors. On the main floor you will find the living room, the kitchen and a terrace. On the lower level, you will find the bedrooms, bathroom  …see more

from $545 / night

$3810 / week

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from $545 / night

15

Vacation villa with swimming pool in Leeward

St. Barts / St. Jean

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Welcome to Villa Zen, a luxury two bedroom villa set amid a tropical garden with wonderful sea views. The villa is located in the exclusive Pointe Milou area of St Barthsng>. The villa is very romantic and provides guests with plenty or outdoor space in matured groun  …see more

from $929 / night

$6503 / week

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from $929 / night

14

Gustavia Vacation villa rental

St. Barts / Gustavia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
QuotVialencquot is one of the last architectural colonial villas of the island. It is located has on an exceptional location at the entrance of Gustavia harbour. The villa dominates the harbour entrance, and the ocean view toward the sunset. The villa has been renovate  …see more

from $1121 / night

$7841 / week

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from $1121 / night

20

Gustavia Vacation villa rental

St. Barts / Gustavia

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the Preservation District of Gustavia, St Barts, and within walking distance of town and Shell Beach. Harbor Crest House HCH is in a perfect location. Furnished with a combination of French country and British West Indies appointments. The style is casual and  …see more

from $1470 / night

$10287 - $19050 / week

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from $1470 / night

(1) Excellent 

12

Vacation villa with swimming pool in Leeward

St. Barts / Colombier

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
We promise you are very unique holiday. The villa is very secluded and yet you are only a few minutes from everything. The views and sunsets from the villa are "Huge". Even the locals who have never been here say "Wow". Large terrace, an edgeless pool, a 5 person Heated  …see more

from $471 / night

$3292 - $8538 / week

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from $471 / night

11

Leeward Vacation villa rental

St. Barts / Gustavia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
The villa Harbour View is situated on the heights of Gustavia, overlooking the harbour. It is located facing the quay or the most beautiful yachts come to moor a superb view. The villa has four rooms including one in a separate bungalow. A large luminous living room ope  …see more

from $1633 / night

$11430 / week

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from $1633 / night

20

Villa rental in Anse des Flamands

St. Barts / Anse des Flamands

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Pet friendly
Villa Tichka will captivate youIt is perfectly located above Flamands beach of facing the sunset ... Not too near the beautiful beach, just enough to give you a privacy, but at a feet distance to go down the stairs in stone in the garden from the beach... From the vill  …see more

from $1035 / night

$7239 / week

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from $1035 / night

11

Leeward Vacation villa rental

St. Barts / Anse des Flamands

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
St Barts Villa Matajagui is a villa made by a passionate.This all white contemporary villa inspires serenityThe infinity pool overlooks the turquoise sea and beach of Flamands located above.The living room is oriented facing the ocean view, and the two large master bedr  …see more

from $817 / night

$5715 / week

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from $817 / night

12

Vacation villa in Leeward

St. Barts / St. Jean

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
La Dsirade is a spacious villa located on the hillside of Saint Jean.It offers a very nice ocean view of Saint Jean Bay and the Eden Roc.The villa is at a short walk from the beach, and near the many shops and restaurants.It is separated into bungalows in a tropical gar  …see more

from $1231 / night

$8611 / week

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from $1231 / night

17

Vacation villa in Gustavia

St. Barts / Gustavia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villla Serenity LJF is a beautiful three bedroom villa built on the hillside overlooking Gustavia, St Barts, and the harbor, with spectacular sunsets. The villa is very spacious and is built on one level, all the rooms open on to the wonderful view.The villa is decorate  …see more

from $5443 / night

$38100 / week

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from $5443 / night

15

Vacation villa in Leeward

St. Jean / St. Jean Beach

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Pet friendly
Villa Challenge CHG is a delightful one bedroom villa located directly on the far end of St. Jean Beach, St Barts. Both the living and the bedroom open to a terrace overlooking the ocean. The sound of the waves lapping against the shore can be heard throughout the house  …see more

from $338 / night

$2363 / week

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from $338 / night

11

Vacation villa in Gustavia

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
La Magnifica is a brand new villa located on the sunrise side of the island.Located hillside in Vitet, this contemporary villa has a wide ocean view on the bay of Toiny.The villa is very well equipped, with large white sofa, a contemporary kitchen, and two very nice t  …see more

from $926 / night

$6477 / week

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from $926 / night

20

Villa rental in Leeward

St. Barts / Gustavia

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
Tatiana a large chic contemporary villa, located hillside in Vitet, with a superb view on the lagoon of Grand Cul de Sac, and the bay of Petit Cul de Sac, and ToinyThis minimalist five bedrooms villa is perfectly well maintained. A large living is open onto a terrace an  …see more

from $4191 / night

$29337 / week

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from $4191 / night

(1) Excellent 

18

Lurin Vacation villa rental

St. Barts / Lurin

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
Vague Bleu is a brand new contemporary villa located on the hillside of Lurin. This new villa is facing the ocean and the sunset addicts of sun will be fully satisfiedWe like in this villaThe deep blue of the infinity pool.The mixes made with the exotic and contempora  …see more

from $2722 / night

$19050 / week

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from $2722 / night

24

Vacation villa rental

St. Barts / Gustavia

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Villa Wings, a luxury 4 bedroom villa in St Barts. This contemporary and new built villa is located in the St-Jean Hillside with breath-taking panoramic views over St Jean Bay. The location of this villa is simple fantastic as you are within a few minutes fro  …see more

from $2857 / night

$20000 - $70000 / week

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from $2857 / night

20

Vacation villa with swimming pool in St. Jean

St. Barts / St. Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Super Sky BBA is located in St. Jean and is built entirely of stone with all natural fabrics and dcor. This is a unique house with two pools. All bedrooms are fairly equal, making this an ideal house for 3 couples. There is a comfortable living room that overlooks  …see more

from $1133 / night

$7925 - $14097 / week

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from $1133 / night