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Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 238 Rentals Available.

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238 Vacation rentals

Filters applied: 4+ Bedrooms

1 / 47

Simpson Bay Villa

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$657.00

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from $657.00 / night

(1)

1 / 46

Simpson Bay Villa

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$843.00

Excellent (1 reviews)

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from $843.00 / night

(1)

1 / 61

Simpson Bay Villa

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,072.00

Excellent (1 reviews)

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from $2,072.00 / night

1 / 43

Simpson Bay Villa

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$643.00

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from $643.00 / night

1 / 33

Simpson Bay House

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$851.00

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from $851.00 / night

1 / 34

Simpson Bay Villa

  • 5
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,498.00

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from $1,498.00 / night

1 / 38

Simpson Bay Villa

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,522.00

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from $1,522.00 / night

1 / 49

Simpson Bay Villa

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

$743.00

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from $743.00 / night

1 / 42

Simpson Bay Villa

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,143.00

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from $1,143.00 / night

1 / 69

Simpson Bay Villa

  • 7
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,215.00

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from $2,215.00 / night

Your search has been expanded 19.7 miles to include more rentals

1 / 30

Orient Bay Villa - 5.6 miles away

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

$638.00

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from $638.00 / night

1 / 44

St. Barthelemy Villa - 18.4 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Air conditioning

$1,714.00

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from $1,714.00 / night

1 / 77

Anse des Cayes Villa - 18.8 miles away

  • 5
  • 14
  • min stay varies
  • Swimming pool
  • Air conditioning

$4,357.00

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from $4,357.00 / night

1 / 46

St. Barthelemy Villa - 19.5 miles away

  • 5
  • 10
  • min stay varies

$8,748.00

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from $8,748.00 / night

1 / 64

St. Barthelemy Villa - 17.3 miles away

  • 5
  • 10
  • min stay varies

$4,286.00

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from $4,286.00 / night

1 / 47

St. Jean Villa - 19.6 miles away

  • 4
  • 8
  • min stay varies

$3,571.00

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from $3,571.00 / night

1 / 67

Lurin Villa - 19.7 miles away

  • 5
  • 10
  • min stay varies

$4,000.00

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from $4,000.00 / night

1 / 71

Gustavia Villa - 19.1 miles away

  • 4
  • 8
  • min stay varies

$3,571.00

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from $3,571.00 / night

1 / 24

Colombier Villa - 18.3 miles away

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

$1,357.00

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from $1,357.00 / night

1 / 100

Lurin Villa - 19.6 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool

$2,100.00

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from $2,100.00 / night

1 / 55

Anse des Cayes Villa - 19 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool

$2,429.00

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from $2,429.00 / night

1 / 71

Lurin Villa - 19.7 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool

$2,679.00

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from $2,679.00 / night

1 / 32

Gustavia Villa - 19.4 miles away

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

$1,214.00

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from $1,214.00 / night

1 / 72

Anse des Cayes Villa - 19 miles away

  • 7
  • 14
  • min stay varies

$6,286.00

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from $6,286.00 / night

1 / 43

Colombier Villa - 18.3 miles away

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

$2,857.00

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from $2,857.00 / night

(1)

1 / 36

Corossol Villa - 18.4 miles away

  • 4
  • 8
  • min stay varies
  • Air conditioning

$1,229.00

Excellent (1 reviews)

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from $1,229.00 / night

1 / 40

St. Barthelemy Villa - 18 miles away

  • 4
  • 8
  • min stay varies

$2,857.00

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from $2,857.00 / night

1 / 38

St. Barthelemy Villa - 18 miles away

  • 4
  • 8
  • min stay varies

$1,143.00

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from $1,143.00 / night

1 / 21

Lurin Villa - 19.7 miles away

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

$1,371.00

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from $1,371.00 / night

1 / 40

St. Barthelemy Villa - 18.1 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Air conditioning

$22,000.00

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from $22,000.00 / night

1 / 35

Lurin Villa - 19.5 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool

$4,571.00

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from $4,571.00 / night

1 / 100

St. Barthelemy Villa - 18.2 miles away

  • 8
  • 16
  • min stay varies
  • Swimming pool
  • Air conditioning

$11,000.00

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from $11,000.00 / night

1 / 35

Colombier Villa - 17.5 miles away

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

$1,714.00

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from $1,714.00 / night

(1)

1 / 93

The Valley Villa - 13.5 miles away

  • 5
  • 14
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 54 minutes

$3,264.00

Excellent (1 reviews)

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from $3,264.00 / night

1 / 75

The Valley Villa - 13.5 miles away

  • 4
  • 8
  • min stay varies
  • Air conditioning
  • Pet friendly
  • Private garden

Responds fast! Avg. 3 hours 54 minutes

$2,119.00

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from $2,119.00 / night

(1)

1 / 35

Orient Bay House - 6.5 miles away

  • 4
  • 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$836.00

Excellent (1 reviews)

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from $836.00 / night

(2)

1 / 26

Orient Bay House - 5.5 miles away

  • 4
  • 8
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$836.00

Excellent (2 reviews)

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from $836.00 / night

(9)

1 / 25

Philipsburg House - 5 miles away

  • 10
  • 20
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,550.00

Excellent (9 reviews)

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from $2,550.00 / night

1 / 28

Lurin Villa - 19.7 miles away

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

$2,946.00

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from $2,946.00 / night

1 / 53

Terres Basses Villa - 3 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$3,928.00

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from $3,928.00 / night