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Simpson Bay Villas & Vacation Rentals with Swimming Pool - 836 Rentals Available.

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836 Vacation rentals

Filters applied: Swimming pool

(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

(3)

1 / 16

Simpson Bay Villa

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

$856.00

Average (3 reviews)

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from $856.00 / night

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 / 29

Simpson Bay Apartment

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

$401.00

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from $401.00 / 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 / 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 / 50

Simpson Bay Villa

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • 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 / 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 / 30

Simpson Bay Villa

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

$729.00

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from $729.00 / 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

(2)

1 / 23

Simpson Bay House

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

$401.00

Very Good (2 reviews)

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from $401.00 / 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 / 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 / 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 / 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 / 20

Simpson Bay Apartment

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

$401.00

Excellent (1 reviews)

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from $401.00 / 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 / 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

1 / 34

Simpson Bay Villa

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

$675.00

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from $675.00 / 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 / 34

Simpson Bay Villa

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

$735.00

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from $735.00 / 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 / 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 / 9

Simpson Bay Apartment

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

$372.00

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from $372.00 / night

(2)

1 / 29

Simpson Bay Apartment

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$286.00

Average (2 reviews)

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from $286.00 / night

1 / 34

Simpson Bay Villa

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

$825.00

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from $825.00 / night

1 / 21

Simpson Bay Villa

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Child friendly

$143.00

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from $143.00 / 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 / 10

Simpson Bay Villa

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

$472.00

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from $472.00 / night

1 / 20

Simpson Bay Villa

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

$829.00

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from $829.00 / night

Your search has been expanded 18.3 miles to include more rentals

(6)

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 (6 reviews)

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from $393.00 / night

(8)

1 / 25

St Martin / St Maarten Villa - 5.5 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$357.00

Excellent (8 reviews)

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from $357.00 / night

1 / 6

Orient Bay Studio - 6.3 miles away

  • -1
  • 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 4 minutes

$98.00

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from $98.00 / night

(1)

1 / 92

The Valley Villa - 13.5 miles away

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$1,900.00

Excellent (1 reviews)

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from $1,900.00 / night

1 / 50

Terres Basses Villa - 3.6 miles away

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

$10,572.00

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from $10,572.00 / night

1 / 27

Anse des Flamands Villa - 18.3 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