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Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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400 Vacation rentals

Corossol Vacation villa rental

Corossol villa

  • 1 bedroom
  • sleeps 2
  • 1 bathroom

from $415 / night

$2,900 - $3,900 / week

1 / 21

St. Jean Vacation villa rental

St. Jean villa

  • 2 bedrooms
  • sleeps 4
  • 2 bathrooms
  • Wi-Fi available

from $1,429 / night

$10,000 - $30,000 / week

1 / 35

St. Jean Vacation villa rental

St. Jean villa

  • 9 bedrooms
  • sleeps 18
  • 9 bathrooms

from $6,916 / night

$48,411 / week

1 / 4

Vacation villa rental

St. Jean villa

  • 5 bedrooms
  • sleeps 10
  • 5 bathrooms
  • Wi-Fi available

from $4,089 / night

$28,625 / week

1 / 41

Vacation villa in Anse des Cayes

Anse des Cayes villa

  • 7 bedrooms
  • sleeps 12
  • 6 bathrooms
  • Wi-Fi available

from $3,142 / night

$22,000 - $125,000 / week

1 / 100

St. Jean Vacation villa rental

St. Jean villa

  • 3 bedrooms
  • sleeps 6
  • 3 bathrooms

from $2,215 / night

$15,500 - $45,000 / week

1 / 33

Vacation villa in Lurin

Lurin villa

  • 5 bedrooms
  • sleeps 10
  • 6 bathrooms

from $4,285 / night

$30,000 - $200,000 / week

1 / 52

Vacation villa with swimming pool in Lurin

Lurin villa

  • 3 bedrooms
  • sleeps 6
  • 3 bathrooms
  • Wi-Fi available

from $1,861 / night

$13,021 - $52,084 / week

1 / 12

Vacation home in St. Jean

St. Jean house

  • 3 bedrooms
  • sleeps 3
  • 2 bathrooms
  • Wi-Fi available

from $1,094 / night

$7,657 / week

1 / 24

Vacation villa rental

Lurin villa

  • 4 bedrooms
  • sleeps 8
  • 4 bathrooms
  • Wi-Fi available

from $2,418 / night

$16,928 - $53,256 / week

1 / 41

Villa rental in Anse des Flamands

Anse des Flamands villa

  • 2 bedrooms
  • sleeps 4
  • 2 bathrooms

from $957 / night

$6,700 - $30,000 / week

1 / 66

Vacation villa in Gustavia

Gustavia villa

  • 3 bedrooms
  • sleeps 6
  • 4 bathrooms

from $3,285 / night

$23,000 - $50,000 / week

1 / 33

St. Jean Vacation villa rental

St. Jean villa

  • 2 bedrooms
  • sleeps 4
  • 2 bathrooms
  • Wi-Fi available

from $2,094 / night

$14,656 / week

1 / 30

Vacation villa with shared pool in St. Jean

St. Jean villa

  • 4 bedrooms
  • sleeps 8
  • 4 bathrooms

from $1,757 / night

$12,300 - $49,000 / week

1 / 100

Vacation villa in Lurin

Lurin villa

  • 2 bedrooms
  • sleeps 6
  • 2 bathrooms
  • Wi-Fi available

from $494 / night

$3,451 - $11,719 / week

1 / 17

Vacation home rental

Lurin house

  • 2 bedrooms
  • sleeps 6
  • 2 bathrooms
  • Wi-Fi available

from $494 / night

$3,451 - $11,719 / week

1 / 16

Vacation villa with swimming pool in Lurin

Lurin villa

  • 2 bedrooms
  • sleeps 6
  • 2 bathrooms
  • Wi-Fi available

from $494 / night

$3,451 - $11,719 / week

1 / 12

Vacation villa in Lurin

Lurin villa

  • 3 bedrooms
  • sleeps 6
  • 3 bathrooms

from $1,857 / night

$13,000 - $55,000 / week

1 / 33

Anse des Cayes Vacation villa rental

Anse des Cayes villa

  • 7 bedrooms
  • sleeps 14
  • 6 bathrooms

from $2,714 / night

$19,000 - $75,000 / week

1 / 96

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 4 bedrooms
  • sleeps 10
  • 3 bathrooms

from $1,714 / night

$12,000 - $50,000 / week

1 / 78

Vacation villa rental

Gustavia villa

  • 8 bedrooms
  • sleeps 16
  • 9 bathrooms

from $3,142 / night

$22,000 - $64,000 / week

1 / 22

Vacation b&b in Anse des Cayes

Anse des Cayes b&b

  • 1 bedroom
  • sleeps 2
  • 1 bathroom
  • Wi-Fi available

from $196 / night

$1,094 / week

1 / 5

Anse des Flamands Vacation villa rental

Anse des Flamands villa

  • 5 bedrooms
  • sleeps 10
  • 5 bathrooms

from $2,142 / night

$15,000 - $95,000 / week

1 / 58

Vacation villa in Lurin

Lurin villa

  • 5 bedrooms
  • sleeps 10
  • 5 bathrooms

from $4,285 / night

$30,000 - $120,000 / week

1 / 38

Vacation villa rental

Lurin villa

  • 3 bedrooms
  • sleeps 6
  • 3 bathrooms

from $2,500 / night

$17,500 - $55,000 / week

1 / 24

Vacation villa rental

Anse des Flamands villa

  • 1 bedroom
  • sleeps 2
  • 1 bathroom

from $1,200 / night

$8,400 / week

1 / 25

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 2 bedrooms
  • sleeps 4
  • 2 bathrooms

from $785 / night

$5,500 - $22,000 / week

1 / 25

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 3 bedrooms
  • sleeps 6
  • 2 bathrooms

from $742 / night

$5,200 - $13,500 / week

1 / 46

Vacation villa with swimming pool in Lurin

Lurin villa

  • 3 bedrooms
  • sleeps 6
  • 3 bathrooms

from $1,245 / night

$8,715 / week

1 / 27

Vacation villa with swimming pool in Lurin

Lurin villa

  • 3 bedrooms
  • sleeps 6
  • 3 bathrooms

from $2,400 / night

$16,800 / week

1 / 32

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 4 bedrooms
  • sleeps 8
  • 4 bathrooms

from $2,428 / night

$17,000 - $80,000 / week

1 / 20

Vacation villa rental

Anse des Cayes villa

  • 4 bedrooms
  • sleeps 8
  • 4 bathrooms

from $2,000 / night

$14,000 - $54,000 / week

1 / 100

Villa rental in St. Jean

St. Jean villa

  • 4 bedrooms
  • sleeps 8
  • 4 bathrooms

from $1,428 / night

$10,000 - $75,000 / week

1 / 33

Gustavia Vacation villa rental

Gustavia villa

  • 4 bedrooms
  • sleeps 10
  • 4 bathrooms

from $5,000 / night

$35,000 - $130,000 / week

1 / 100

Vacation villa in St. Jean

St. Jean villa

  • 4 bedrooms
  • sleeps 8
  • 4 bathrooms

from $2,714 / night

$19,000 - $80,000 / week

1 / 45

St. Jean Vacation villa accommodation

St. Jean villa

  • 4 bedrooms
  • sleeps 8
  • 4 bathrooms

from $4,285 / night

$30,000 - $120,000 / week

1 / 40

Vacation villa in Gustavia

Gustavia villa

  • 8 bedrooms
  • sleeps 18
  • 9 bathrooms

from $4,500 / night

$31,500 / week

1 / 22

Vacation villa in St. Jean

St. Jean villa

  • 5 bedrooms
  • sleeps 10
  • 5 bathrooms

from $3,750 / night

$26,250 / week

1 / 30

Vacation villa with swimming pool in Gustavia

Gustavia villa

  • 5 bedrooms
  • sleeps 10
  • 5 bathrooms

from $1,275 / night

$8,925 / week

1 / 25

Vacation villa with swimming pool in Anse des Flamands

Anse des Flamands villa

  • 5 bedrooms
  • sleeps 10
  • 5 bathrooms

from $4,500 / night

$31,500 / week

1 / 36

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