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Simpson Bay Villas & Vacation Rentals - 811 Rentals Available

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811 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. 3 hours 14 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
  • 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

$1,272.00

Excellent (1 reviews)

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from $1,272.00 / 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

(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)

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

$630.00

Very Good (3 reviews)

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from $630.00 / 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

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 / 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

Your search has been expanded 19.6 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

1 / 69

The Valley Villa - 13.5 miles away

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

Responds fast! Avg. 58 minutes

$1,432.00

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from $1,432.00 / 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 / 6

Orient Bay Studio - 6.3 miles away

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

Responds fast! Avg. 46 minutes

$96.00

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from $96.00 / night

1 / 27

Cupecoy Bay Villa - 2.6 miles away

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

$760.00

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from $760.00 / night

1 / 44

St. Barthelemy Villa - 18.4 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Air conditioning

$1,714.00

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from $1,714.00 / night

1 / 39

Lurin Villa - 19.6 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool

$686.00

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from $686.00 / night

1 / 32

St. Barthelemy Villa - 18.3 miles away

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

$471.00

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from $471.00 / night

(1)

1 / 20

St. Barthelemy Villa - 17.9 miles away

  • 3
  • 6
  • min stay varies

$600.00

Very Good (1 reviews)

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from $600.00 / night

1 / 77

Anse des Cayes Villa - 18.8 miles away

  • 5
  • 14
  • min stay varies
  • Swimming pool
  • Air conditioning

$4,357.00

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from $4,357.00 / night

1 / 46

St. Barthelemy Villa - 19.5 miles away

  • 5
  • 10
  • min stay varies

$8,748.00

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from $8,748.00 / night