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Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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2,088 Vacation rentals

Anse des Cayes ski apartment to rent.

Anse des Cayes apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $306 / night

$2,142 / week

1 / 9

Villa rental in Colombier

Colombier villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

from $678 / night

$4,746 / week

1 / 22

Vacation home in Gustavia

Gustavia house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $290 / night

$2,030 / week

1 / 18

Villa rental in Corossol

Corossol villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 4

from $3,006 / night

$21,042 / week

1 / 24

Anse des Flamands Vacation home rental

Anse des Flamands house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

from $371 / night

$2,597 / week

1 / 30

Anse des Cayes Vacation villa rental

Anse des Cayes villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $875 / night

$6,125 / week

1 / 9

Anse des Cayes Vacation villa rental

Anse des Cayes villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $2,011 / night

$14,077 / week

1 / 30

Anse des Cayes Vacation villa rental

Anse des Cayes villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,209 / night

$8,463 / week

1 / 27

Villa rental in Anse des Cayes

Anse des Cayes villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,997 / night

$13,979 / week

1 / 22

Home rental in Colombier

Colombier house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $228 / night

$1,596 / week

1 / 28

Vacation villa in Anse des Cayes

Anse des Cayes villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $3,883 / night

$27,181 / week

1 / 23

Vacation villa in Colombier

Colombier villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $593 / night

$4,151 / week

1 / 21

Vacation villa in Anse des Cayes

Anse des Cayes villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

from $1,802 / night

$12,614 / week

1 / 22

Vacation villa in St. Jean

St. Jean villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $2,316 / night

$16,212 / week

1 / 30

Gustavia ski villa to rent.

Gustavia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $3,772 / night

$26,404 / week

1 / 30

Vacation villa in St. Jean

St. Jean villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $2,580 / night

$18,060 / week

1 / 20

Villa rental in Anse des Cayes

Anse des Cayes villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from $945 / night

$6,615 / week

1 / 23

Vacation villa in St. Jean

St. Jean villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $3,379 / night

$23,653 / week

1 / 29

Ski villa to rent in Gustavia

Gustavia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $2,638 / night

$18,466 / week

1 / 25

St. Jean ski villa to rent.

St. Jean villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,099 / night

$7,693 / week

1 / 24

Ski villa to rent in St. Jean

St. Jean villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from $4,243 / night

$29,701 / week

1 / 30

Vacation apartment in Anse des Flamands

Anse des Flamands apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $233 / night

$1,631 / week

1 / 16

Apartment rental in Gustavia

Gustavia apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from $395 / night

$2,765 / week

1 / 18

Anse des Cayes ski villa to rent.

Anse des Cayes villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from $560 / night

$3,920 / week

1 / 12

Villa rental in Gustavia

Gustavia villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $1,102 / night

$7,714 / week

1 / 15

Villa rental in Colombier

Colombier villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $967 / night

$6,769 / week

1 / 30

Vacation villa in St. Jean

St. Jean villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $1,999 / night

$13,993 / week

1 / 16

Vacation villa in Anse des Cayes

Anse des Cayes villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,868 / night

$13,076 / week

1 / 30

Vacation home in St. Jean

St. Jean house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $2,799 / night

$19,593 / week

1 / 30

Villa rental in Gustavia

Gustavia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

from $3,926 / night

$27,482 / week

1 / 25

Ski villa to rent in St. Jean

St. Jean villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from $2,952 / night

$20,664 / week

1 / 30

Vacation apartment in Gustavia

Gustavia apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from $260 / night

$1,820 / week

1 / 14

Anse des Flamands Vacation villa rental

Anse des Flamands villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from $606 / night

$4,242 / week

1 / 21

Home rental in St. Jean

St. Jean house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,035 / night

$7,245 / week

1 / 24

Vacation villa in St. Jean

St. Jean villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $2,875 / night

$20,125 / week

1 / 30

Anse des Flamands Vacation villa rental

Anse des Flamands villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from $1,482 / night

$10,374 / week

1 / 19

Vacation villa in Gustavia

Gustavia villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $1,148 / night

$8,036 / week

1 / 24

Anse des Flamands Vacation villa rental

Anse des Flamands villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,511 / night

$10,577 / week

1 / 24

Ski home to rent in Anse des Flamands

Anse des Flamands house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $175 / night

$1,225 / week

1 / 30

Vacation villa in St. Jean

St. Jean villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 12

from $11,220 / night

$78,540 / week

1 / 30

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