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Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 40 Rentals Available.

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22 Vacation rentals

Filters applied: 4 Bedrooms

(5)

1 / 43

Simpson Bay Villa

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

$844

Excellent (5 reviews)

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from $844 / night

1 / 28

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $850 / night

1 / 30

Simpson Bay Villa

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

from $658 / night

1 / 28

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

from $615 / night

1 / 10

Simpson Bay Villa

  • 5
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1071

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from $1071 / night

1 / 38

Simpson Bay House

  • 5
  • 10
  • Min stay varies
  • Child friendly
  • Air conditioning

from $605 / night

1 / 10

Simpson Bay Villa

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

from $793 / night

(1)

1 / 31

Simpson Bay Villa

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

$649

Excellent (1 reviews)

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from $649 / night

1 / 7

Simpson Bay Villa

  • 5
  • 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1441

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from $1441 / night

1 / 41

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$1144

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from $1144 / night

1 / 50

Simpson Bay Villa

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

$1129

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from $1129 / night

1 / 26

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children

$3287

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from $3287 / night

1 / 40

Simpson Bay Villa

  • 5
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1010

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from $1010 / night

1 / 22

Simpson Bay Villa

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

from $701 / night

1 / 23

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $858 / night

1 / 46

Simpson Bay Villa

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

from $504 / night

1 / 48

Simpson Bay Villa

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

from $504 / night

1 / 24

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1815

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from $1815 / night

(1)

1 / 39

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$643

Very Good (1 reviews)

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from $643 / night

1 / 30

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1800

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from $1800 / night

(1)

1 / 61

Simpson Bay Villa

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

$1815

Excellent (1 reviews)

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from $1815 / night

1 / 22

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children

$1500

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from $1500 / night

Your search has been expanded 2.6 miles to include more rentals

1 / 47

St. Maarten-St. Martin Villa - 1.6 miles away

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

from $462 / night

1 / 24

St. Maarten-St. Martin Villa - 1.7 miles away

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

from $605 / night

1 / 9

St. Maarten-St. Martin Villa - 1.7 miles away

  • 5
  • 12
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1080

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from $1080 / night

1 / 45

Cole Bay Villa - 1.7 miles away

  • 5
  • 10
  • Min stay varies
  • Ask about children
  • Ask about pets

from $787 / night

1 / 20

St. Maarten-St. Martin Villa - 1.8 miles away

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

from $462 / night

1 / 15

Cole Bay Villa - 1.8 miles away

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1123

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from $1123 / night

1 / 38

St. Maarten-St. Martin Villa - 1.8 miles away

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

from $598 / night

1 / 15

St. Maarten-St. Martin House - 1.9 miles away

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

from $345 / night

1 / 34

Maho Villa - 2.2 miles away

  • 5
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $706 / night

1 / 49

Marigot Villa - 2.2 miles away

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

from $809 / night

1 / 52

Maho House - 2.2 miles away

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

from $649 / night

1 / 26

Cole Bay Villa - 2.3 miles away

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

from $533 / night

1 / 55

Maho Villa - 2.3 miles away

  • 5
  • 10
  • Min stay varies
  • Child friendly
  • Ask about pets

from $648 / night

1 / 26

Sint Maarten Villa - 2.4 miles away

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

from $643 / night

1 / 24

Cole Bay Villa - 2.5 miles away

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

from $663 / night

(1)

1 / 27

St. Maarten-St. Martin House - 2.5 miles away

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

$371

Excellent (1 reviews)

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from $371 / night

1 / 24

Mullet Bay Villa - 2.6 miles away

  • 5
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1153

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from $1153 / night

1 / 44

Mullet Bay House - 2.6 miles away

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

$1153

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from $1153 / night