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Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 311 Rentals Available.

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311 Vacation rentals

Filters applied: 4+ Bedrooms

1 / 47

Simpson Bay Villa

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

$843.00

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from $843.00 / night

(1)

1 / 46

Simpson Bay Villa

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

$1,272.00

Excellent (1 reviews)

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from $1,272.00 / night

(1)

1 / 61

Simpson Bay Villa

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

$3,001.00

Excellent (1 reviews)

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from $3,001.00 / night

1 / 43

Simpson Bay Villa

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

$1,386.00

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from $1,386.00 / night

1 / 42

Simpson Bay Villa

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$850.00

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from $850.00 / night

1 / 37

Simpson Bay Villa

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

$766.00

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from $766.00 / night

1 / 33

Simpson Bay House

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

$850.00

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from $850.00 / night

Your search has been expanded 19.5 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)

1 / 95

The Valley Villa - 13.5 miles away

  • 4
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 9 minutes

$2,176.00

Excellent (1 reviews)

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from $2,176.00 / night

1 / 10

Blowing Point House - 9.2 miles away

  • 5
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,700.00

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from $1,700.00 / 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 / 25

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 / 21

St. Barthelemy Villa - 18 miles away

  • 4
  • 8
  • min stay varies

$1,143.00

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from $1,143.00 / night

1 / 32

St. Barthelemy Villa - 18.4 miles away

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

$1,429.00

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from $1,429.00 / 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

$5,714.00

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from $5,714.00 / 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 / 100

Terres Basses Villa - 3.4 miles away

  • 14
  • 28
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$4,143.00

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from $4,143.00 / night

1 / 31

Terres Basses Villa - 2.6 miles away

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

$1,000.00

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from $1,000.00 / night

1 / 100

St. Barthelemy Villa - 18.2 miles away

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

$10,000.00

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from $10,000.00 / night

1 / 47

St. Barthelemy Villa - 19.5 miles away

  • 5
  • 10
  • min stay varies

$7,727.00

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from $7,727.00 / night

1 / 45

Terres Basses Villa - 2.6 miles away

  • 4
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$743.00

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from $743.00 / night

1 / 69

Terres Basses Villa - 2.6 miles away

  • 9
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$6,429.00

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from $6,429.00 / 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 / 33

Terres Basses Villa - 3.2 miles away

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

$1,714.00

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from $1,714.00 / night

1 / 32

Terres Basses Villa - 3.5 miles away

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

$1,071.00

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from $1,071.00 / night

1 / 50

Terres Basses Villa - 2.4 miles away

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

$1,470.00

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from $1,470.00 / night

1 / 54

Terres Basses Villa - 2.6 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$643.00

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from $643.00 / night

1 / 21

Terres Basses Villa - 2.6 miles away

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

$743.00

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from $743.00 / night

1 / 22

Terres Basses Villa - 3.4 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$1,000.00

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from $1,000.00 / night

1 / 28

Cole Bay Villa - 2.4 miles away

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

$1,765.00

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from $1,765.00 / night

(2)

1 / 20

Terres Basses House - 3 miles away

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

$2,072.00

Excellent (2 reviews)

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from $2,072.00 / night

(3)

1 / 21

Anse Marcel Villa - 6.3 miles away

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

$2,143.00

Very Good (3 reviews)

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from $2,143.00 / night

1 / 22

Oyster Pond Villa - 5.5 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$815.00

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from $815.00 / night

1 / 40

Terres Basses House - 2.5 miles away

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

$972.00

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from $972.00 / night

1 / 68

Terres Basses House - 2.7 miles away

  • 12
  • 24
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,786.00

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from $2,786.00 / night

(2)

1 / 29

Oyster Pond House - 5.3 miles away

  • 4
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$643.00

Very Good (2 reviews)

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from $643.00 / night

1 / 77

St Martin / St Maarten Villa - 3.2 miles away

  • 14
  • 26
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$12,858.00

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from $12,858.00 / night