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Simpson Bay Waterfront Villas, Vacation Rentals & More - 788 Rentals Available.

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788 Vacation rentals

Filters applied: Waterfront

(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 57 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

$657.00

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from $657.00 / night

1 / 29

Simpson Bay Apartment

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

$272.00

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from $272.00 / night

1 / 39

Simpson Bay Villa

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$758.00

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from $758.00 / night

(1)

1 / 46

Simpson Bay Villa

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

$843.00

Excellent (1 reviews)

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from $843.00 / 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

$2,072.00

Excellent (1 reviews)

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from $2,072.00 / 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
  • Private garden

$286.00

Excellent (1 reviews)

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from $286.00 / night

(1)

1 / 29

Simpson Bay Villa

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

$557.00

Excellent (1 reviews)

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from $557.00 / 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

$336.00

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from $336.00 / 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

$643.00

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from $643.00 / night

(1)

1 / 20

Simpson Bay Condo

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

$230.00

Excellent (1 reviews)

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from $230.00 / night

1 / 40

Simpson Bay Apartment

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

$350.00

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from $350.00 / night

1 / 16

Simpson Bay Villa

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

$557.00

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from $557.00 / night

(1)

1 / 21

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 Villa

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

$692.00

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from $692.00 / night

(3)

1 / 17

Simpson Bay Apartment

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

$482.00

Very Good (3 reviews)

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from $482.00 / 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

$200.00

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from $200.00 / 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

$272.00

Average (2 reviews)

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from $272.00 / 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
  • Air conditioning

$215.00

Excellent (1 reviews)

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from $215.00 / night

(1)

1 / 24

Simpson Bay Condo

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

$343.00

Excellent (1 reviews)

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from $343.00 / night

1 / 27

Simpson Bay Apartment

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

$529.00

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from $529.00 / night

1 / 20

Simpson Bay House

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

$572.00

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from $572.00 / night

1 / 34

Simpson Bay Villa

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

$1,498.00

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from $1,498.00 / night

1 / 42

Simpson Bay Villa

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

$1,143.00

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from $1,143.00 / night

1 / 38

Simpson Bay Villa

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

$1,522.00

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from $1,522.00 / night

1 / 35

Simpson Bay Condo

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

$300.00

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from $300.00 / night

(1)

1 / 62

Simpson Bay Villa

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

$700.00

Very Good (1 reviews)

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from $700.00 / night

1 / 49

Simpson Bay Villa

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

$743.00

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from $743.00 / night

1 / 69

Simpson Bay Villa

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

$2,215.00

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from $2,215.00 / night

1 / 32

Simpson Bay Condo

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

$358.00

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from $358.00 / night

Your search has been expanded 5.6 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