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Windward Vacation Rentals & Homes - 1367 Rentals Available

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1,367 Vacation rentals

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(8)

1 / 25

St Martin / St Maarten Villa - 16.3 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$410.00

Excellent (8 reviews)

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from $410.00 / night

1 / 6

Orient Bay Studio - 18.7 miles away

  • -1
  • 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 4 minutes

$90.00

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from $90.00 / night

(19)

1 / 18

Philipsburg Apartment - 15.6 miles away

  • 1
  • 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Air conditioning

Responds fast! Avg. 3 hours 27 minutes

$98.00

Excellent (19 reviews)

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from $98.00 / night

(4)

1 / 15

Philipsburg Apartment - 15.7 miles away

  • 1
  • 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

Responds fast! Avg. 3 hours 27 minutes

$109.00

Excellent (4 reviews)

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from $109.00 / night

1 / 30

Orient Bay Villa - 18.4 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool

Responds fast! Avg. 1 hour 51 minutes

$638.00

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from $638.00 / night

(2)

1 / 17

Orient Bay Apartment - 17.8 miles away

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 4 minutes

$167.00

Very Good (2 reviews)

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from $167.00 / night

(1)

1 / 24

Orient Bay Condo - 18.6 miles away

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$83.00

Excellent (1 reviews)

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from $83.00 / night

1 / 24

Lurin Villa - 1.3 miles away

  • 2
  • 4
  • 4 nights min
  • Child friendly
  • Pet friendly

$328.00

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from $328.00 / night

1 / 20

Colombier Villa - 1.9 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Air conditioning

$1,429.00

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from $1,429.00 / night

1 / 45

Cole Bay House - 18.4 miles away

  • 5
  • 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$922.00

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from $922.00 / night

1 / 40

Lurin Villa - 1.1 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool

$943.00

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from $943.00 / night

1 / 65

Gouverneur Villa - 1.1 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool

$2,714.00

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from $2,714.00 / night

1 / 38

Gustavia Villa - 1.3 miles away

  • 1
  • 2
  • min stay varies

$286.00

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from $286.00 / night

1 / 35

Lurin Villa - 1.4 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool

$4,571.00

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from $4,571.00 / night

1 / 30

St. Barthelemy Villa - 0.1 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Air conditioning

$686.00

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from $686.00 / night

1 / 46

Petit Cul de Sac Villa - 2.2 miles away

  • 6
  • 12
  • min stay varies

$3,000.00

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from $3,000.00 / night

1 / 33

Lurin Villa - 0.1 miles away

  • 3
  • 6
  • min stay varies

$2,286.00

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from $2,286.00 / night

1 / 46

Petit Cul de Sac Villa - 2.4 miles away

  • 4
  • 8
  • 4 nights min
  • Swimming pool

$700.00

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from $700.00 / night

1 / 61

Marigot Villa - 1.3 miles away

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Pet friendly

$643.00

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from $643.00 / night

1 / 42

Anse des Cayes Villa - 1.2 miles away

  • 3
  • 6
  • min stay varies

$786.00

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from $786.00 / night

1 / 34

St. Jean Villa - 0.1 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,614.00

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from $1,614.00 / night

1 / 28

Corossol Villa - 1.6 miles away

  • 3
  • 6
  • 4 nights min

$1,857.00

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from $1,857.00 / night

1 / 31

St. Barthelemy Villa - 1.5 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Air conditioning

$1,057.00

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from $1,057.00 / night

1 / 22

Corossol Villa - 1.9 miles away

  • 1
  • 2
  • 4 nights min
  • Swimming pool
  • Air conditioning

$357.00

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from $357.00 / night

1 / 71

Lurin Villa - 1.1 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool

$2,679.00

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from $2,679.00 / night

1 / 65

Lurin Villa - 0.1 miles away

  • 2
  • 6
  • min stay varies

$1,043.00

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from $1,043.00 / night

1 / 26

Lurin Villa - 1.3 miles away

  • 2
  • 4
  • min stay varies

$563.00

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from $563.00 / night

1 / 27

St. Jean Villa - 1.5 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$700.00

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from $700.00 / night

1 / 26

St. Barthelemy Villa - 1.1 miles away

  • 3
  • 6
  • 4 nights min
  • Child friendly
  • Pet friendly

$542.00

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from $542.00 / night

1 / 20

St. Barthelemy Villa - 2 miles away

  • 3
  • 6
  • min stay varies
  • Ask about children
  • Ask about pets

$564.00

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from $564.00 / night

1 / 29

St. Jean Villa - 0.1 miles away

  • 2
  • 4
  • min stay varies

$714.00

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from $714.00 / night

1 / 23

St. Barthelemy Villa - 1.8 miles away

  • 2
  • 4
  • 4 nights min
  • Child friendly
  • Pet friendly

$456.00

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from $456.00 / night

1 / 19

Gustavia Villa - 1.3 miles away

  • 2
  • 4
  • 4 nights min
  • Child friendly
  • Pet friendly

$600.00

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from $600.00 / night

1 / 30

Anse de Lorient Villa - 0.1 miles away

  • 2
  • 4
  • 4 nights min
  • Child friendly
  • Pet friendly

$643.00

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from $643.00 / night

(2)

1 / 30

Petit Cul de Sac Villa - 2.3 miles away

  • 3
  • 6
  • min stay varies

$929.00

Excellent (2 reviews)

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from $929.00 / night

(1)

1 / 45

Corossol Villa - 1.7 miles away

  • 1
  • 2
  • 4 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

$858.00

Excellent (1 reviews)

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from $858.00 / night

1 / 22

St. Barthelemy Villa - 1.7 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Air conditioning

$929.00

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from $929.00 / night

1 / 25

Philipsburg Villa - 15.9 miles away

  • 7
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,300.00

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from $1,300.00 / night

1 / 24

Gustavia Villa - 1.3 miles away

  • 5
  • 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,214.00

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from $1,214.00 / night

1 / 61

St. Barthelemy Villa - 2.1 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Air conditioning

$1,571.00

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from $1,571.00 / night