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Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 270 Rentals Available.

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270 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

$3,000.00

Excellent (1 reviews)

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from $3,000.00 / 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 / 37

Simpson Bay Villa

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

$747.00

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from $747.00 / 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 19.7 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)

1 / 95

The Valley Villa - 13.5 miles away

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

Responds fast! Avg. 58 minutes

$2,176.00

Excellent (1 reviews)

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from $2,176.00 / night

1 / 27

Terres Basses Villa - 2.8 miles away

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

$842.00

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from $842.00 / night

1 / 22

Anse des Flamands Villa - 18.3 miles away

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

$2,714.00

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from $2,714.00 / night

1 / 38

St. Jean Villa - 19.7 miles away

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

$1,018.00

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from $1,018.00 / night

1 / 100

Anse des Cayes Villa - 18.7 miles away

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$4,139.00

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from $4,139.00 / night

1 / 33

Anse des Cayes Villa - 18.5 miles away

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

$2,307.00

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from $2,307.00 / night

1 / 22

Gustavia Villa - 19.5 miles away

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

$3,529.00

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from $3,529.00 / night

1 / 42

Terres Basses Villa - 3.6 miles away

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

$6,108.00

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from $6,108.00 / night

1 / 65

Terres Basses Villa - 3.3 miles away

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

$1,065.00

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from $1,065.00 / night

1 / 22

Gustavia Villa - 19.5 miles away

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

$3,257.00

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from $3,257.00 / night

1 / 39

Terres Basses Villa - 2.7 miles away

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

$1,017.00

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from $1,017.00 / night

1 / 46

Terres Basses Villa - 2.7 miles away

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

$706.00

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from $706.00 / night

1 / 28

Terres Basses Villa - 2.7 miles away

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

$910.00

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from $910.00 / night

1 / 34

Terres Basses Villa - 3.1 miles away

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

$950.00

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from $950.00 / night

1 / 21

The Valley Villa - 13.5 miles away

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

$1,805.00

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from $1,805.00 / night

1 / 31

Anse des Cayes Villa - 18.8 miles away

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

$2,036.00

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from $2,036.00 / night

1 / 59

Gustavia Villa - 19.5 miles away

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

$4,343.00

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from $4,343.00 / night

1 / 57

Terres Basses Villa - 2.9 miles away

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

$1,629.00

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from $1,629.00 / night

1 / 38

Anse des Flamands Villa - 18.2 miles away

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

$1,086.00

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from $1,086.00 / night

1 / 33

Anse des Flamands Villa - 17.7 miles away

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

$1,221.00

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from $1,221.00 / night

1 / 36

Terres Basses Villa - 3.5 miles away

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

$679.00

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from $679.00 / night

1 / 25

Gustavia Villa - 19.4 miles away

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

$1,154.00

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from $1,154.00 / night

1 / 31

Anse des Cayes Villa - 19.1 miles away

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

$5,294.00

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from $5,294.00 / night

1 / 37

Terres Basses Villa - 2.7 miles away

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

$2,036.00

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from $2,036.00 / night

(1)

1 / 44

Terres Basses Villa - 3.8 miles away

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

$1,168.00

Excellent (1 reviews)

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from $1,168.00 / night

1 / 22

Gustavia Villa - 19.5 miles away

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

$2,714.00

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from $2,714.00 / night

1 / 39

Terres Basses Villa - 2.7 miles away

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

$1,628.00

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from $1,628.00 / night

1 / 27

Terres Basses Villa - 2.9 miles away

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

$950.00

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from $950.00 / night

1 / 40

Cupecoy Bay Villa - 2.6 miles away

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

$883.00

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from $883.00 / night

1 / 40

Terres Basses Villa - 2.3 miles away

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

$1,561.00

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from $1,561.00 / night

1 / 37

Terres Basses Villa - 3.4 miles away

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

$950.00

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from $950.00 / night

1 / 22

Gustavia Villa - 19.5 miles away

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

$2,986.00

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from $2,986.00 / night

1 / 22

Gustavia Villa - 19.5 miles away

  • 8
  • 18
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$3,937.00

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from $3,937.00 / night