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Simpson Bay 3-bedroom Villas, Vacation Rentals & More - 719 Rentals Available.

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719 Vacation rentals

Filters applied: 3+ 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 / 39

Simpson Bay Villa

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$858.00

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from $858.00 / 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 / 13

Simpson Bay Villa

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

$572.00

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from $572.00 / night

1 / 25

Simpson Bay Villa

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

$543.00

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from $543.00 / night

1 / 26

Simpson Bay Apartment

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

$454.00

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from $454.00 / night

1 / 50

Simpson Bay Villa

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,143.00

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from $1,143.00 / 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)

1 / 30

Simpson Bay Villa

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$729.00

Excellent (1 reviews)

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from $729.00 / night

1 / 46

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)

1 / 29

Simpson Bay Villa

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

$429.00

Excellent (1 reviews)

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from $429.00 / night

1 / 50

Simpson Bay Villa

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

$672.00

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from $672.00 / night

(2)

1 / 23

Simpson Bay House

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

$400.00

Very Good (2 reviews)

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from $400.00 / night

1 / 22

Simpson Bay Villa

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

$809.00

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from $809.00 / night

1 / 40

Simpson Bay Apartment

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

$572.00

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from $572.00 / night

1 / 0

Simpson Bay Villa

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

$700.00

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from $700.00 / night

1 / 16

Simpson Bay Villa

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

$729.00

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from $729.00 / night

1 / 29

Simpson Bay House

  • 3
  • 6
  • 4 nights min
  • Ask about children
  • Ask about pets

$342.00

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from $342.00 / night

1 / 39

Simpson Bay House

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

$1,200.00

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from $1,200.00 / night

1 / 19

Simpson Bay Apartment

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

$643.00

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from $643.00 / night

1 / 0

Simpson Bay Villa

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

$787.00

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from $787.00 / night

Your search has been expanded 19.9 miles to include more rentals

(7)

1 / 26

St Martin / St Maarten Villa - 1.1 miles away

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Swimming pool
“Our family spent a wonderful week at La Casita on Beacon Hill. The home was spacious, extremely clean, very well furnished and private. We loved the fact that we felt in our own world, with an amazing view of the sea and sunsets were beyond words....”
- Review left on 12/28/2010

$393.00

Excellent (7 reviews)

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from $393.00 / night

1 / 30

Orient Bay Villa - 5.6 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

1 / 59

The Valley Villa - 13.5 miles away

  • 3
  • 6
  • min stay varies
  • Air conditioning
  • Pet friendly
  • Private garden

$1,250.00

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from $1,250.00 / night

1 / 0

Terres Basses Villa - 3.5 miles away

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

$715.00

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from $715.00 / night

1 / 20

Anse des Cayes Villa - 18.8 miles away

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

Responds fast! Avg. 1 hour 5 minutes

$1,857.00

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from $1,857.00 / night

1 / 22

Gustavia Villa - 19.1 miles away

  • 8
  • 16
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 5 minutes

$2,857.00

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from $2,857.00 / night

1 / 33

Anguilla Villa - 12.6 miles away

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

Responds fast! Avg. 1 hour 5 minutes

$2,000.00

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from $2,000.00 / night

1 / 0

Anse des Cayes Villa - 18.8 miles away

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

$2,143.00

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from $2,143.00 / night

1 / 29

St. Jean Villa - 19.7 miles away

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

$929.00

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from $929.00 / night

1 / 32

Gustavia Villa - 19.1 miles away

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

$2,857.00

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from $2,857.00 / night

1 / 38

St. Jean Villa - 19.9 miles away

  • 4
  • 8
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 5 minutes

$4,286.00

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from $4,286.00 / night

1 / 0

Anse Marcel Villa - 6.2 miles away

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

$400.00

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from $400.00 / night

1 / 32

Anse des Flamands Villa - 18.2 miles away

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

$1,200.00

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from $1,200.00 / night

(9)

1 / 20

Philipsburg House - 5 miles away

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

$1,193.00

Excellent (9 reviews)

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from $1,193.00 / night

1 / 0

Cupecoy Bay Villa - 2.6 miles away

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

$815.00

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from $815.00 / night

1 / 0

Anse des Cayes Villa - 18.7 miles away

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

$3,286.00

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from $3,286.00 / night

1 / 0

Anse des Cayes Villa - 18.8 miles away

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

$1,857.00

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from $1,857.00 / night

1 / 25

Anse des Flamands Villa - 18 miles away

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

Responds fast! Avg. 1 hour 5 minutes

$1,143.00

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from $1,143.00 / night

1 / 37

Island Harbour Villa - 15.2 miles away

  • 4
  • 8
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 5 minutes

$1,400.00

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from $1,400.00 / night