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50 Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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456 Vacation rentals

Vacation villa with swimming pool in Gustavia

Gustavia villa

3 bedrooms • 4 bathrooms • sleeps 6

from $662 / night

$4,629 / week

1 / 20

Vacation villa in Colombier

Colombier villa

2 bedrooms • 1 bathroom • sleeps 2

from $603 / night

$4,214 - $9,682 / week

1 / 12

Vacation villa with swimming pool in Colombier

Colombier villa

1 bedroom • 2 bathrooms • sleeps 2

from $578 / night

$4,701 / week

1 / 22

Vacation home with swimming pool in Colombier

Colombier house

2 bedrooms • 2 bathrooms • sleeps 4

from $390 / night

$2,730 / week

1 / 24

Vacation villa in Colombier

Colombier villa

2 bedrooms • 2 bathrooms • sleeps 4

from $650 / night

$4,550 - $9,617 / week

1 / 7

Vacation cottage with shared pool in St. Jean

St. Jean cottage

1 bedroom • 1 bathroom • sleeps 2

from $765 / night

$5,355 / week

1 / 23

Vacation b&b with swimming pool in Anse des Cayes

Anse des Cayes b&b

1 bedroom • 1 bathroom • sleeps 2

from $204 / night

$1,143 / week

1 / 5

St. Jean Vacation cottage rental

St. Jean cottage

1 bedroom • 1 bathroom • sleeps 2

from $792 / night

$5,540 / week

1 / 6

Vacation villa with swimming pool in Anse des Flamands

Anse des Flamands villa

1 bedroom • 1 bathroom • sleeps 2

from $598 / night

$4,182 - $13,488 / week

1 / 17

Lurin Vacation villa rental

Lurin villa

2 bedrooms • 2 bathrooms • sleeps 6

from $509 / night

$3,555 - $12,072 / week

1 / 13

Vacation villa rental

Colombier villa

4 bedrooms • 4 bathrooms • sleeps 8

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 - $80,000 / week

1 / 24

St. Jean Vacation cottage rental

St. Jean cottage

1 bedroom • 1 bathroom • sleeps 2

from $926 / night

$6,479 / week

1 / 10

Colombier Vacation villa rental

Colombier villa

3 bedrooms • 3 bathrooms • sleeps 6

from $801 / night

$12,144 / week

1 / 30

Vacation villa in Gustavia

Gustavia villa

2 bedrooms • 2 bathrooms • sleeps 4

from $820 / night

$5,737 - $34,336 / week

1 / 28

Vacation villa in St. Jean

St. Jean villa

6 bedrooms • 6 bathrooms • sleeps 12

from $28,346 / night

$198,418 / week

1 / 12

Vacation villa rental

Lurin villa

4 bedrooms • 4 bathrooms • sleeps 8

from $2,126 / night

$14,881 - $55,330 / 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 $1,127 / night

$7,887 / 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

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

from $509 / night

$3,555 - $12,072 / week

1 / 15

Vacation villa with swimming pool in Lurin

Lurin villa

2 bedrooms • 2 bathrooms • sleeps 6

from $512 / night

$3,579 - $12,155 / week

1 / 12

Vacation villa rental

Lurin villa

2 bedrooms • 2 bathrooms • sleeps 6

from $509 / night

$3,555 - $12,072 / week

1 / 15

Vacation villa in Lurin

Lurin villa

2 bedrooms • 2 bathrooms • sleeps 6

from $512 / night

$3,581 - $12,159 / week

1 / 17

Vacation b&b in Anse des Cayes

Anse des Cayes b&b

1 bedroom • 1 bathroom • sleeps 2

from $202 / night

$1,127 / week

1 / 5

Vacation villa with swimming pool in Lurin

Lurin villa

3 bedrooms • 3 bathrooms • sleeps 6

from $1,530 / night

$10,703 - $36,122 / 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

from $778 / night

$5,446 / week

1 / 8

Vacation home rental

Lurin house

2 bedrooms • 2 bathrooms • sleeps 6

from $509 / night

$3,555 - $12,072 / week

1 / 16

Vacation villa with swimming pool in Gustavia

Gustavia villa

2 bedrooms • 2 bathrooms • sleeps 4

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

from $1,401 / night

$9,805 - $42,710 / week

1 / 35

Vacation villa with swimming pool in Gustavia

Gustavia villa

4 bedrooms • 3 bathrooms • sleeps 8

from $912 / night

$4,557 - $22,748 / week

1 / 34

Vacation villa in Colombier

Colombier villa

2 bedrooms • 2 bathrooms • sleeps 4

from $958 / night

$6,700 - $30,000 / week

1 / 22

Vacation home with swimming pool in Anse des Flamands

Anse des Flamands house

3 bedrooms • 3 bathrooms • sleeps 6

from $1,056 / night

$7,384 - $29,266 / week

1 / 21

Vacation villa with swimming pool in Anse des Flamands

Anse des Flamands villa

3 bedrooms • 3 bathrooms • sleeps 6

from $1,056 / night

$7,384 - $29,265 / week

1 / 14

Vacation villa rental

Anse des Cayes villa

2 bedrooms • 2 bathrooms • sleeps 4

from $450 / night

$3,150 - $8,925 / week

1 / 12

Villa rental in Anse des Cayes with swimming pool, golf nearby

Anse des Cayes villa

2 bedrooms • 2 bathrooms • sleeps 4

from $440 / night

$3,991 - $9,488 / week

1 / 43

Vacation villa in Lurin

Lurin villa

2 bedrooms • 2 bathrooms • sleeps 4

from $342 / night

$2,400 - $7,500 / week

1 / 24

Lurin Vacation villa rental

Lurin villa

3 bedrooms • 3 bathrooms • sleeps 6

from $2,286 / night

$16,000 - $50,000 / week

1 / 33

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