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Simpson Bay 2-bedroom Villas, Vacation Rentals & More - 772 Rentals Available.

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772 Vacation rentals

Filters applied: 2+ Bedrooms

(11)

1 / 34

Simpson Bay Apartment

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

Responds fast! Avg. 2 hours 4 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 / 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

$415.00

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from $415.00 / 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)

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)

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 / 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
  • Air conditioning

$672.00

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from $672.00 / 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 / 41

Simpson Bay Apartment

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

$500.00

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from $500.00 / 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 / 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

(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 / 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

(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

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

$572.00

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from $572.00 / 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 / 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)

1 / 20

Simpson Bay Yacht

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

$2,000.00

Excellent (1 reviews)

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from $2,000.00 / night

1 / 32

Simpson Bay Condo

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

$386.00

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from $386.00 / 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 / 61

Simpson Bay Villa

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

$613.00

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from $613.00 / 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 / 33

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 / 37

Simpson Bay Villa

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

$766.00

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from $766.00 / night

Your search has been expanded 19.7 miles to include more rentals

(6)

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 (6 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

$410.00

Excellent (8 reviews)

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from $410.00 / night

(3)

1 / 17

Orient Bay Apartment - 6.2 miles away

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

Responds fast! Avg. 45 minutes

$165.00

Very Good (3 reviews)

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from $165.00 / night

1 / 24

La Savane Villa - 4.3 miles away

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

$933.00

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from $933.00 / night

1 / 38

La Savane Villa - 4.3 miles away

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

$809.00

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from $809.00 / night

1 / 39

Terres Basses Villa - 2.7 miles away

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

$1,462.00

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from $1,462.00 / night

1 / 34

Long Bay Village Villa - 10.6 miles away

  • 7
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$4,875.00

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from $4,875.00 / night

1 / 41

Terres Basses Villa - 3.5 miles away

  • 7
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$4,806.00

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from $4,806.00 / night

1 / 18

Anse des Flamands Villa - 18.3 miles away

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

$460.00

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from $460.00 / night

1 / 37

Lurin Villa - 19.7 miles away

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

$3,900.00

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from $3,900.00 / night