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Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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1,170 Vacation rentals

Gustavia Vacation townhouse rental

Gustavia townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from $1,123 / night

$9,962 / week

1 / 12

Vacation b&b in Anse des Cayes

Anse des Cayes b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $187 / night

$1,047 / week

1 / 5

Vacation villa in Gustavia

Gustavia villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $2,001 / night

$14,005 - $61,268 / week

1 / 73

St. Jean Vacation villa rental

St. Jean villa

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

from $12,857 / night

$90,000 - $390,000 / week

1 / 100

Vacation villa in Lurin

Lurin villa

  • 9 bedrooms
  • 8 bathrooms
  • sleeps 18

from $12,857 / night

$90,000 - $300,000 / week

1 / 89

Vacation villa rental

Gustavia villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $642 / night

$4,500 - $9,900 / week

1 / 8

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

Vacation villa in St. Jean

St. Jean villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $485 / night

$3,395 / week

1 / 21

Vacation villa rental

Anse des Flamands villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $785 / night

$5,500 - $17,000 / week

1 / 95

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $628 / night

$4,400 - $21,000 / week

1 / 49

Vacation villa in Gouverneur

Gouverneur villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

from $1,214 / night

$8,500 - $24,000 / week

1 / 31

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $785 / night

$5,500 - $16,500 / week

1 / 21

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 $7,857 / night

$55,000 - $225,000 / week

1 / 100

Vacation villa in Lurin

Lurin villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,185 / night

$8,300 - $33,000 / week

1 / 87

Vacation villa rental

Anse des Flamands villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $400 / night

$2,800 - $8,000 / week

1 / 16

Villa rental in Lurin

Lurin villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $1,285 / night

$9,000 - $28,000 / week

1 / 95

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $714 / night

$5,000 - $14,500 / week

1 / 15

Vacation villa in St. Jean

St. Jean villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $1,285 / night

$9,000 - $45,000 / week

1 / 40

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,102 / night

$7,715 - $20,000 / week

1 / 62

Vacation villa in Lurin

Lurin villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $2,000 / night

$14,000 - $70,000 / week

1 / 91

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 rental

Anse des Flamands villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,500 / night

$10,500 - $30,000 / week

1 / 45

Villa rental in Lurin

Lurin villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $1,785 / night

$12,500 - $35,000 / week

1 / 71

Villa rental in Gustavia

Gustavia villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $714 / night

$5,000 - $15,000 / week

1 / 100

Vacation villa in Anse des Cayes

Anse des Cayes villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $628 / night

$4,400 - $20,000 / week

1 / 56

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $857 / night

$6,000 - $22,000 / week

1 / 25

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

Villa rental in Gustavia

Gustavia villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,000 / night

$7,000 - $30,000 / week

1 / 34

Gouverneur Vacation villa rental

Gouverneur villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $957 / night

$6,700 - $27,000 / week

1 / 26

Vacation villa in St. Jean

St. Jean villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,307 / night

$9,150 - $28,500 / week

1 / 100

Gustavia Vacation villa rental

Gustavia villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from $2,142 / night

$15,000 - $150,000 / week

1 / 100

Colombier Vacation villa rental

Colombier villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $1,000 / night

$7,000 - $35,000 / week

1 / 99

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $1,928 / night

$13,500 - $35,500 / week

1 / 81

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

Vacation villa in Anse des Flamands

Anse des Flamands villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $3,571 / night

$25,000 - $110,000 / week

1 / 54

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 in Lurin

Lurin villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from $4,285 / night

$30,000 - $200,000 / week

1 / 52

Gustavia Vacation villa rental

Gustavia villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $428 / night

$3,000 - $4,900 / week

1 / 72

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