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Simpson Bay Villas & Vacation Rentals with Swimming Pool - 583 Rentals Available.

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583 Vacation rentals

Filters applied: Swimming pool

(11)

1 / 34

Simpson Bay Apartment

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

Responds fast! Avg. 1 hour 53 minutes

$409.00

Excellent (11 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 / 29

Simpson Bay Apartment

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

$415.00

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from $415.00 / 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 / 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
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$586.00

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from $586.00 / 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 / 50

Simpson Bay Villa

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

$672.00

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from $672.00 / night

(1)

1 / 29

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 / 41

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

(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

(2)

1 / 29

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 / 43

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 / 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 / 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 / 61

Simpson Bay Villa

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

$598.00

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from $598.00 / night

1 / 37

Simpson Bay Villa

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

$747.00

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from $747.00 / 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)

1 / 42

Simpson Bay Apartment

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

$572.00

Excellent (1 reviews)

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from $572.00 / 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

(2)

1 / 36

Simpson Bay Apartment

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

$343.00

Average (2 reviews)

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from $343.00 / night

1 / 33

Simpson Bay House

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

$850.00

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from $850.00 / night

Your search has been expanded 13.5 miles to include more rentals

1 / 30

Orient Bay Villa - 5.6 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool

$638.00

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from $638.00 / 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

$491.00

Excellent (8 reviews)

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from $491.00 / night

1 / 6

Orient Bay Studio - 6.3 miles away

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

Responds fast! Avg. 42 minutes

$88.00

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from $88.00 / night

(1)

1 / 95

The Valley Villa - 13.5 miles away

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

Responds fast! Avg. 58 minutes

$2,176.00

Excellent (1 reviews)

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from $2,176.00 / night

1 / 16

Terres Basses Villa - 2.7 miles away

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

$611.00

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from $611.00 / night

1 / 22

Cul de Sac Apartment - 6.4 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$189.00

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from $189.00 / night

(8)

1 / 26

St Martin / St Maarten Villa - 1.1 miles away

  • 3
  • 6
  • min stay varies
  • 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

$428.00

Excellent (8 reviews)

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from $428.00 / night

(4)

1 / 17

Orient Bay Apartment - 6.2 miles away

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

Responds fast! Avg. 49 minutes

$176.00

Excellent (4 reviews)

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from $176.00 / night

(1)

1 / 24

Orient Bay Condo - 6.3 miles away

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

$145.00

Excellent (1 reviews)

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from $145.00 / night

1 / 10

Blowing Point House - 9.2 miles away

  • 5
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,700.00

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from $1,700.00 / night

(2)

1 / 25

Orient Bay House - 5.5 miles away

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

$836.00

Excellent (2 reviews)

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from $836.00 / night

(1)

1 / 35

Orient Bay House - 6.5 miles away

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

$836.00

Excellent (1 reviews)

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from $836.00 / night

1 / 15

Orient Bay Condo - 6.1 miles away

  • 1
  • 3
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$120.00

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from $120.00 / night

(1)

1 / 17

Oyster Pond Apartment - 5.5 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$229.00

Excellent (1 reviews)

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from $229.00 / night

(8)

1 / 69

Philipsburg House - 5.2 miles away

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

$2,072.00

Excellent (8 reviews)

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from $2,072.00 / night

1 / 30

Cole Bay Villa - 2.4 miles away

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

$1,286.00

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from $1,286.00 / night