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Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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459 Vacation rentals

Colombier Vacation villa rental

Colombier villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,189 / night

$8,323 / week

1 / 30

Villa rental in St. Jean with swimming pool

St. Jean villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $3,206 / night

$20,897 - $48,663 / week

1 / 37

Vacation b&b in Anse des Cayes

Anse des Cayes b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $183 / night

$1,025 / week

1 / 5

Vacation villa in Colombier

Colombier villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $602 / night

$4,208 - $4,524 / week

1 / 13

Colombier Vacation villa rental

Colombier villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $665 / night

$4,649 - $6,613 / week

1 / 49

St. Jean Vacation villa rental

St. Jean villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $1,286 / night

$9,000 - $45,000 / week

1 / 27

St. Jean Vacation villa rental

St. Jean villa

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

from $12,857 / night

$90,000 - $200,000 / week

1 / 100

Vacation villa in Lurin

Lurin villa

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 18

from $17,142 / night

$120,000 - $195,000 / week

1 / 100

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $771 / night

$5,400 - $13,500 / week

1 / 46

Vacation villa in Gustavia

Gustavia villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $700 / night

$4,900 - $19,000 / week

1 / 19

Villa rental in St. Jean

St. Jean villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $540 / night

$3,780 / week

1 / 14

Gustavia Vacation villa rental

Gustavia villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $1,000 / night

$7,000 - $35,000 / week

1 / 24

Vacation villa rental

St. Jean villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $750 / night

$5,250 - $25,000 / week

1 / 22

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $742 / night

$5,200 - $35,000 / week

1 / 33

Vacation villa in Gustavia

Gustavia villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $746 / night

$5,216 / week

1 / 28

Vacation villa in Anse des Cayes

Anse des Cayes villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $700 / night

$4,900 - $19,000 / week

1 / 45

Villa rental in Anse des Flamands

Anse des Flamands villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $12,785 / night

$89,500 - $450,000 / week

1 / 100

Vacation villa in Gouverneur

Gouverneur villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $5,714 / night

$40,000 - $225,000 / week

1 / 100

Villa rental in St. Jean

St. Jean villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $657 / night

$4,600 - $15,000 / week

1 / 38

Villa rental in Gustavia

Gustavia villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $714 / night

$5,000 - $15,000 / week

1 / 100

Vacation villa with swimming pool in Anse des Cayes

Anse des Cayes villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $3,880 / night

$27,160 / week

1 / 56

Villa rental in Anse des Cayes

Anse des Cayes villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,000 / night

$7,000 - $19,500 / week

1 / 100

St. Jean Vacation villa rental

St. Jean villa

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

from $7,099 / night

$47,174 - $102,249 / week

1 / 62

Vacation villa with swimming pool in Anse des Cayes

Anse des Cayes villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $3,464 / night

$24,248 / week

1 / 56

Vacation villa in Lurin

Lurin villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $2,142 / night

$15,000 - $70,000 / week

1 / 71

Vacation villa in Lurin

Lurin villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,428 / night

$10,000 - $38,000 / week

1 / 99

Vacation villa with swimming pool in St. Jean

St. Jean villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $3,049 / night

$21,343 / week

1 / 56

Vacation villa in Lurin

Lurin villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $342 / night

$2,400 - $8,000 / week

1 / 24

Vacation home in Anse des Cayes

Anse des Cayes house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $364 / night

$2,544 / week

1 / 16

Vacation villa in Anse des Cayes

Anse des Cayes villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $592 / night

$4,150 - $20,000 / week

1 / 56

Vacation villa rental

Anse des Flamands villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $600 / night

$4,200 - $11,500 / week

1 / 26

Vacation villa in Lurin

Lurin villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $647 / night

$4,530 - $22,000 / week

1 / 27

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,428 / night

$10,000 - $27,500 / week

1 / 100

Vacation villa in Gustavia

Gustavia villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $2,071 / night

$14,500 - $42,000 / week

1 / 99

Vacation villa with swimming pool in St. Jean

St. Jean villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $3,521 / night

$24,618 - $53,586 / week

1 / 32

Vacation villa with swimming pool in Anse des Cayes

Anse des Cayes villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $3,049 / night

$21,343 / week

1 / 55

Gustavia Vacation villa rental

Gustavia villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from $2,142 / night

$15,000 - $150,000 / week

1 / 100

Lurin Vacation villa rental

Lurin villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $2,356 / night

$16,492 / week

1 / 23

Colombier Vacation villa rental

Colombier villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $957 / night

$6,700 - $30,000 / week

1 / 99

St. Jean Vacation villa rental

St. Jean villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $3,429 / night

$24,000 - $80,000 / week

1 / 33

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