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Simpson Bay Villas & Vacation Rentals - 928 Rentals Available

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928 Vacation rentals

(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 58 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 / 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 / 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
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning

$429.00

Excellent (1 reviews)

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from $429.00 / 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

1 / 42

Simpson Bay Villa

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$850.00

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from $850.00 / 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)

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

  • 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)

1 / 20

Simpson Bay Yacht

  • 3
  • 6
  • 1 night min
  • Ask about children
  • Ask about pets

$2,001.00

Excellent (1 reviews)

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from $2,001.00 / 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 / 9

Simpson Bay Apartment

  • 1
  • 2
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

$286.00

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from $286.00 / 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

(1)

1 / 13

Simpson Bay Studio

  • -1
  • 2
  • min stay varies
  • Child friendly
  • Air conditioning

$300.00

Excellent (1 reviews)

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from $300.00 / night

Your search has been expanded 19.5 miles to include more rentals

(19)

1 / 18

Philipsburg Apartment - 4.6 miles away

  • 1
  • 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Air conditioning

Responds fast! Avg. 3 hours 25 minutes

$98.00

Excellent (19 reviews)

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from $98.00 / night

1 / 69

The Valley Villa - 13.5 miles away

  • 3
  • 6
  • min stay varies
  • Air conditioning
  • Pet friendly
  • Private garden

Responds fast! Avg. 1 hour 5 minutes

$1,432.00

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from $1,432.00 / 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

(1)

1 / 22

Orient Bay House - 6.1 miles away

  • 2
  • 2
  • min stay varies
  • Child friendly
  • Air conditioning

$275.00

Excellent (1 reviews)

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from $275.00 / 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. 42 minutes

$163.00

Excellent (4 reviews)

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from $163.00 / 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

(8)

1 / 25

St Martin / St Maarten Villa - 5.5 miles away

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

$491.00

Excellent (8 reviews)

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from $491.00 / night

1 / 41

Gustavia Villa - 19.5 miles away

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

$2,571.00

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from $2,571.00 / night