50 Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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1,460 Vacation rentals

(1) Excellent 

6

St. Barts / Anse des Cayes

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children

from $108 / night

$753 / week

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from $108 / 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

from $302 / night

$1829 - $4948 / week

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from $302 / night

(1) Excellent 

23

St. Barts / Colombier

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

from $398 / night

$3765 / week

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from $398 / night

20

St. Barts / Gustavia

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $428 / night

$2996 / week

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from $428 / night

58

St. Barts / Gustavia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $857 / night

$6000 - $28500 / week

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from $857 / night

23

Vacation villa rental

St. Barts / Colombier

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Villa Belle Bague, one of the most luxurious 4 bedroom villa rental located high on the hillside in Colombier in St. Barts. With its high cliffs and long white beaches, and breath taking views, St. Barts is one of the Caribbean's most enticing island …see more

Pricing unknown

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10

St. Barts / Colombier

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $742 / night

$5184 / week

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from $742 / night

22

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. Facing the sea and 500 metres from local shops, sights and restaurants, this beautif …see more

from $544 / night

$3788 - $11772 / week

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from $544 / night

24

Vacation villa with swimming pool in Anse des Flamands

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 $1072 / night

$7500 - $22000 / week

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from $1072 / night

12

St. Barts / Anse des Cayes

1 2 14 nights min

  • 1 bedroom
  • Sleeps 2
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $208 / night

$1447 / week

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from $208 / night

12

St. Barts / Gustavia

1 2 6 nights min

  • 1 bedroom
  • Sleeps 2
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $355 / night

$2479 / week

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from $355 / night

7

Vacation villa in Colombier

St. Barts / Colombier

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Ask about children
  • Air conditioning
  • Private garden
We promise you are very unique holiday. The villa is very secluded. The views and sunsets are "Huge" Large terrace, edgeless pool and 5 person Heated Spa. Comfortable loungers and hammocks with a large living room and open plan luxury kitchen. Two fully air-conditioned …see more

from $615 / night

$4300 / week

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from $615 / night

24

Vacation villa with swimming pool in Gustavia

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Welcome to Villa Ted, a luxury 2 bedroom villa located in the beautiful surroundings of Dévé in St Barths. The villa offers guests a beautiful outdoor terrace area with ample space and provides stunning panoramic view of the over Grand Cul de Sac and the island of Tortu …see more

from $724 / night

$5060 - $22700 / week

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from $724 / night

13

St. Barts / Gustavia

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Child friendly
  • Ask about pets

from $812 / night

$5680 / week

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from $812 / night

16

St. Barts / Gustavia

2 4 Min stay varies

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

from $428 / night

$3000 - $8000 / week

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from $428 / night

15

St. Barts / Gustavia

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

from $591 / night

$4131 / week

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from $591 / night

33

St. Barts / Gustavia

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $743 / night

$5196 / week

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from $743 / night

(1) Excellent 

10

St. Barts / St. Jean

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from $344 / night

$2402 / week

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from $344 / night

15

Vacation villa with swimming pool in St. Jean

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 grounds …see more

from $1000 / night

$7000 - $16500 / week

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from $1000 / night

12

St. Barts / Gustavia

1 2 6 nights min

  • 1 bedroom
  • Sleeps 2
  • 6 nights min
  • Child friendly
  • Ask about pets

from $664 / night

$4648 / week

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from $664 / night

24

Vacation villa rental

St. Barts / St. Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Welcome to Villa Ellena, a stunning and truly magical St Barths Villa rental. This luxury 3 bedroom villa is located midway between St. Jean and the village of Lorient and offers panoramic views over the turquoise St Jean Bay. Designed by an owner/architect wit …see more

from $1716 / night

$12000 - $32000 / week

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from $1716 / 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

from $516 / night

$3615 - $4648 / week

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from $516 / night

(1) Excellent 

12

Vacation villa with swimming pool in Colombier

St. Barts / Colombier

2 2 4 nights min

  • 2 bedrooms
  • Sleeps 2
  • 4 nights min
  • 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

$3290 / week

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from $471 / night

4

St. Barts / Gustavia

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $856 / night

$5992 / week

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from $856 / night

40

Vacation villa with swimming pool in Gustavia

St. Barts / Gustavia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Located in gorgeous Gustavia, this bright villa is perfectly located for exploring the tropical island of St. Barths, promising an unforgettable holiday for up to 8 people. The plush living space is ideal for relaxing after a day in the sun. Enjoy a good book or one of …see more

from $978 / night

$6843 - $19547 / week

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from $978 / night

67

St. Barts / St. Jean

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $871 / night

$6092 - $7125 / week

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from $871 / night

(1) Very Good 

23

St. Barts / St. Jean

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly

from $812 / night

$5680 - $6092 / week

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from $812 / night

(1) Excellent 

15

Vacation villa rental

Anse des Flamands / Flamands Beach

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Villa Triagoz is a private villa offered for vacation rental at the delightful St Barts. When you arrive, prepare to be blown away by the beauty of the place. With a private heated pool, three Rooms (two Master bedrooms,+one baby room), Villa Triagoz is a single floor v …see more

from $600 / night

$4200 - $22000 / week

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from $600 / night

23

St. Barts / Gustavia

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $656 / night

$4596 / week

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from $656 / night

26

Vacation villa with swimming pool in St. Jean

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 Diamond, one of the most exquisite villa rental in St Jean, St Barth. The newly built villa boasts a stunningly beautiful and stylish design with breath-taking views. The villa is centrally located on the St Jean hillside overlooking St. Jean Bay with a …see more

from $1072 / night

$7500 - $25000 / week

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from $1072 / night

24

Vacation villa with shared pool in Anse des Flamands

St. Barts / Anse des Flamands

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Flamands Beach Villa a stunning villa located directly on the pristine, white sands of Baie de Flamands one of St. Barth's most beautiful beaches. Flamands Beach Villa comes with a private jacuzzi and panoramic ocean views over the azure, glistening Caribbea …see more

from $6562 / night

$45930 / week

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from $6562 / night

74

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

from $415 / night

$2900 - $13680 / week

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from $415 / 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

24

Vacation villa rental

St. Barts / Lurin

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Acamar, one of the most stunning 3 bedroom villas with private pool and incredible sea views located over looking Toiny Beach. As you enter this exceptional villa, the view to the exquisitely furnished sitting room, sun terrace, lovely heated swimming pool an …see more

from $1787 / night

$12500 - $40000 / week

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from $1787 / night

24

Vacation villa rental

St. Barts / St. Jean

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Terre Indigo, one of the most stunning 4 bedroom luxury villa rentals in St. Barths. Terre Indigo is located in the popular area of St. Jean offering breath-taking panoramic views of the bay and azure sea beyond. Saint Jean is second in size to the C …see more

from $1572 / night

$11000 - $50000 / week

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from $1572 / night

80

St. Barts / St. Jean

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

from $416 / night

$2900 - $15000 / week

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from $416 / night

45

St. Barts / Gustavia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly

from $685 / night

$4800 - $17100 / week

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from $685 / night

(1) Excellent 

21

St. Barts / St. Jean

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

from $253 / night

$1770 - $5376 / week

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from $253 / night

50

St. Barts / Gustavia

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly

from $644 / night

$4504 - $12312 / week

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from $644 / night

24

Vacation villa with swimming pool in St. Jean

St. Barts / St. Jean

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Villa Isabella, a lovely 4 bedroom villa rental with private pool and breathtaking panoramic views located on the hillside over looking Saint Jean Bay. The lovely town of St Jean is less then half a kilometre from Villa Isabella. Saint Jean is second …see more

from $2287 / night

$16000 - $45000 / week

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from $2287 / night

1