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Simpson Bay Villas & Vacation Rentals with Swimming Pool - 540 Rentals Available.

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540 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

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 / 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 / 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 / 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 / 50

Simpson Bay Villa

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

$672.00

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from $672.00 / 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 / 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)

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)

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 / 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 / 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

(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

(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 / 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 / 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 / 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

(2)

1 / 36

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 / 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

$1,200.00

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from $1,200.00 / night

1 / 0

Simpson Bay Villa

  • 2
  • 4
  • 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

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

Your search has been expanded 19.3 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

(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 / 6

Orient Bay Studio - 6.3 miles away

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

Responds fast! Avg. 1 hour 11 minutes

$92.00

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from $92.00 / night

(4)

1 / 15

Philipsburg Apartment - 4.6 miles away

  • 1
  • 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

Responds fast! Avg. 3 hours 42 minutes

$109.00

Excellent (4 reviews)

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from $109.00 / 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)

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)

1 / 24

Orient Bay Condo - 6.3 miles away

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$84.00

Excellent (1 reviews)

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from $84.00 / night

(1)

1 / 17

Orient Bay Apartment - 6.2 miles away

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 11 minutes

$170.00

Excellent (1 reviews)

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from $170.00 / night

1 / 26

St. Barthelemy Villa - 19.3 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool

$920.00

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from $920.00 / night

1 / 34

Gustavia Villa - 19.1 miles away

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

$3,286.00

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from $3,286.00 / night