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Simpson Bay 2-bedroom Villas, Vacation Rentals & More - 986 Rentals Available.

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986 Vacation rentals

Filters applied: 2+ Bedrooms

(10)

1 / 17

Simpson Bay Apartment

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$409.00

Excellent (10 reviews)

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from $409.00 / night

1 / 47

Simpson Bay Villa

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

$572.00

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from $572.00 / night

(1)

1 / 14

Simpson Bay Apartment

  • 2
  • 4
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$515.00

Excellent (1 reviews)

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from $515.00 / 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 / 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 / 29

Simpson Bay Apartment

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

$400.00

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from $400.00 / 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)

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)

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

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 / 25

Simpson Bay Apartment

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

$329.00

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from $329.00 / 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)

1 / 20

Simpson Bay Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$400.00

Excellent (1 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

(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 / 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

(3)

1 / 14

Simpson Bay Apartment

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

$643.00

Excellent (3 reviews)

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from $643.00 / night

1 / 32

Simpson Bay Condo

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

$529.00

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from $529.00 / night

1 / 40

Simpson Bay Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$465.00

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from $465.00 / night

(3)

1 / 13

Simpson Bay Apartment

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$519.00

Very Good (3 reviews)

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from $519.00 / 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 / 39

Simpson Bay House

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

$572.00

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from $572.00 / night

1 / 0

Simpson Bay Villa

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

$643.00

Inquire

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

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 / 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

Your search has been expanded 19.7 miles to include more rentals

(8)

1 / 25

St Martin / St Maarten Villa - 5.5 miles away

  • 3
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$358.00

Excellent (8 reviews)

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from $358.00 / night

(1)

1 / 92

The Valley Villa - 13.5 miles away

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

$1,900.00

Excellent (1 reviews)

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from $1,900.00 / night

1 / 0

Gustavia Villa - 19.4 miles away

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

$1,000.00

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from $1,000.00 / night

1 / 0

Cupecoy Bay Villa - 2.6 miles away

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

$929.00

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from $929.00 / 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 / 2

Lurin Villa - 19.7 miles away

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

$2,000.00

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from $2,000.00 / night

1 / 0

Anse des Flamands Villa - 17.7 miles away

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

$936.00

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from $936.00 / night

1 / 0

Anse des Cayes Villa - 18.5 miles away

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

$1,714.00

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from $1,714.00 / night

1 / 0

Gustavia Villa - 19.5 miles away

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

$4,571.00

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from $4,571.00 / night