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50 Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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417 Vacation rentals

Vacation villa with swimming pool in Gustavia

Gustavia villa

3 bedrooms • 4 bathrooms • sleeps 6

from $616 / night

$4,308 / week

1 / 20

Vacation villa in Colombier

Colombier villa

2 bedrooms • 1 bathroom • sleeps 2

5 reviews

from $608 / night

$4,247 - $9,757 / week

1 / 12

Vacation villa with swimming pool in Colombier

Colombier villa

1 bedroom • 2 bathrooms • sleeps 2

1 review

from $586 / night

$4,766 / week

1 / 22

Vacation home with swimming pool in Colombier

Colombier house

2 bedrooms • 2 bathrooms • sleeps 4

from $406 / night

$2,837 / week

1 / 24

Vacation villa in Colombier

Colombier villa

2 bedrooms • 2 bathrooms • sleeps 4

2 reviews

from $659 / night

$4,616 - $9,757 / week

1 / 7

Vacation cottage with shared pool in St. Jean

St. Jean cottage

1 bedroom • 1 bathroom • sleeps 2

6 reviews

from $776 / night

$5,433 / week

1 / 23

Vacation b&b with swimming pool in Anse des Cayes

Anse des Cayes b&b

1 bedroom • 1 bathroom • sleeps 2

6 reviews

from $188 / night

$1,049 / week

1 / 5

St. Jean Vacation cottage rental

St. Jean cottage

1 bedroom • 1 bathroom • sleeps 2

3 reviews

from $236 / night

$1,652 / week

1 / 6

Vacation villa with swimming pool in Anse des Flamands

Anse des Flamands villa

1 bedroom • 1 bathroom • sleeps 2

2 reviews

from $614 / night

$4,293 - $13,847 / week

1 / 17

Lurin Vacation villa rental

Lurin villa

2 bedrooms • 2 bathrooms • sleeps 6

1 review

from $517 / night

$3,612 - $12,265 / week

1 / 13

Vacation villa rental

Colombier villa

4 bedrooms • 4 bathrooms • sleeps 8

1 review

from $2,572 / night

$18,000 - $55,000 / week

1 / 23

Vacation villa rental

Gustavia villa

4 bedrooms • 5 bathrooms • sleeps 8

from $2,858 / night

$20,000 - $70,000 / week

1 / 24

St. Jean Vacation cottage rental

St. Jean cottage

1 bedroom • 1 bathroom • sleeps 2

3 reviews

from $349 / night

$2,440 / week

1 / 10

Villa rental in Colombier with swimming pool

Colombier villa

4 bedrooms • 4 bathrooms • sleeps 8

from $2,140 / night

$14,980 / week

1 / 21

Colombier Vacation villa rental

Colombier villa

3 bedrooms • 3 bathrooms • sleeps 6

from $830 / night

$12,585 / week

1 / 30

Vacation villa in Gustavia

Gustavia villa

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from $849 / night

$5,940 - $35,550 / week

1 / 28

Vacation villa in St. Jean

St. Jean villa

6 bedrooms • 6 bathrooms • sleeps 12

from $25,118 / night

$175,826 / week

1 / 12

Vacation villa rental

Lurin villa

4 bedrooms • 4 bathrooms • sleeps 8

from $2,139 / night

$14,977 - $55,687 / week

1 / 41

Anse des Cayes Vacation villa rental

Anse des Cayes villa

3 bedrooms • 4 bathrooms • sleeps 8

from $1,358 / night

$9,500 - $33,500 / week

1 / 22

Vacation home in St. Jean

St. Jean house

3 bedrooms • 2 bathrooms • sleeps 3

from $837 / night

$5,867 - $13,108 / week

1 / 24

St. Jean Vacation villa rental

St. Jean villa

3 bedrooms • 3 bathrooms • sleeps 6

from $2,215 / night

$15,500 - $45,000 / week

1 / 33

Vacation villa with swimming pool in St. Jean

St. Jean villa

2 bedrooms • 2 bathrooms • sleeps 4

2 reviews

from $1,072 / night

$7,500 - $25,000 / week

1 / 26

Vacation villa with swimming pool in Lurin

Lurin villa

2 bedrooms • 2 bathrooms • sleeps 6

3 reviews

from $520 / night

$3,636 - $12,348 / week

1 / 15

Vacation villa in Anse des Cayes

Anse des Cayes villa

2 bedrooms • 2 bathrooms • sleeps 5

from $1,374 / night

$9,612 / week

1 / 19

Vacation villa with swimming pool in Lurin

Lurin villa

2 bedrooms • 2 bathrooms • sleeps 6

from $526 / night

$3,678 - $12,491 / week

1 / 12

Vacation villa rental

Lurin villa

2 bedrooms • 2 bathrooms • sleeps 6

1 review

from $519 / night

$3,628 - $12,320 / week

1 / 15

Vacation villa in Lurin

Lurin villa

2 bedrooms • 2 bathrooms • sleeps 6

from $527 / night

$3,679 - $12,495 / week

1 / 17

Vacation b&b in Anse des Cayes

Anse des Cayes b&b

1 bedroom • 1 bathroom • sleeps 2

from $188 / night

$1,050 / week

1 / 5

Vacation villa with swimming pool in Lurin

Lurin villa

3 bedrooms • 3 bathrooms • sleeps 6

from $1,591 / night

$11,131 - $37,567 / week

1 / 12

Vacation villa rental

Lurin villa

3 bedrooms • 3 bathrooms • sleeps 6

from $2,500 / night

$17,500 - $55,000 / week

1 / 24

Vacation cottage rental

St. Jean cottage

1 bedroom • 1 bathroom • sleeps 2

1 review

from $211 / night

$1,477 / week

1 / 8

Vacation home rental

Lurin house

2 bedrooms • 2 bathrooms • sleeps 6

from $526 / night

$3,678 - $12,491 / week

1 / 16

Vacation villa with swimming pool in Gustavia

Gustavia villa

2 bedrooms • 2 bathrooms • sleeps 4

from $870 / night

$6,092 / week

1 / 30

Vacation villa with swimming pool in Gustavia

Gustavia villa

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from $858 / night

$6,000 - $17,000 / week

1 / 24

Vacation villa with swimming pool in Anse des Flamands

Anse des Flamands villa

4 bedrooms • 4 bathrooms • sleeps 8

6 reviews

from $1,448 / night

$10,135 - $44,146 / week

1 / 35

Vacation villa with swimming pool in Gustavia

Gustavia villa

4 bedrooms • 3 bathrooms • sleeps 8

from $1,326 / night

$6,627 - $33,125 / week

1 / 34

Vacation villa in Colombier

Colombier villa

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from $858 / night

$6,000 - $30,000 / week

1 / 22

Vacation home with swimming pool in Anse des Flamands

Anse des Flamands house

3 bedrooms • 3 bathrooms • sleeps 6

5 reviews

from $1,102 / night

$7,711 - $30,561 / week

1 / 21

Vacation villa with swimming pool in Anse des Flamands

Anse des Flamands villa

3 bedrooms • 3 bathrooms • sleeps 6

1 review

from $1,075 / night

$7,523 - $29,818 / week

1 / 14

Vacation villa rental

Anse des Cayes villa

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from $450 / night

$3,150 - $8,925 / week

1 / 12

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