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Simpson Bay 2-bedroom Villas, Vacation Rentals & More - 40 Rentals Available.

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27 Vacation rentals

Filters applied: 2 Bedrooms

1 / 25

Simpson Bay Apartment

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

from $259 / night

1 / 23

Simpson Bay Villa

  • 2
  • 4
  • Min stay varies
  • Child friendly
  • Ask about pets

from $314 / night

(3)

1 / 13

Simpson Bay Apartment

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

$340

Very Good (3 reviews)

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from $340 / night

1 / 9

Simpson Bay Apartment

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

from $372 / night

1 / 20

Simpson Bay Apartment

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

from $272 / night

1 / 22

Simpson Bay Villa

  • 2
  • 4
  • 5 nights min

from $234 / night

1 / 22

Simpson Bay Apartment

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

from $259 / night

1 / 24

Simpson Bay House

  • 2
  • 6
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning

from $259 / night

(1)

1 / 14

Simpson Bay Apartment

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

$259

Excellent (1 reviews)

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from $259 / night

(3)

1 / 19

Simpson Bay Apartment

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

$315

Excellent (3 reviews)

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from $315 / night

(2)

1 / 14

Simpson Bay Apartment

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

$326

Excellent (2 reviews)

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from $326 / night

1 / 38

Simpson Bay Apartment

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

from $265 / night

1 / 18

Simpson Bay Apartment

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

from $314 / night

(1)

1 / 31

Simpson Bay Apartment

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

$343

Excellent (1 reviews)

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from $343 / night

1 / 13

Simpson Bay Villa

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $729 / night

1 / 19

Simpson Bay Apartment

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

from $343 / night

(1)

1 / 29

Simpson Bay Villa

  • 3
  • 6
  • Min stay varies
  • Child friendly
  • Air conditioning

$259

Excellent (1 reviews)

Inquire

from $259 / night

1 / 13

Simpson Bay Villa

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

from $359 / night

1 / 33

Simpson Bay Villa

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

from $543 / night

1 / 16

Simpson Bay Villa

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

from $500 / night

1 / 45

Simpson Bay Villa

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

from $359 / night

1 / 18

Simpson Bay Apartment

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

from $280 / night

(2)

1 / 23

Simpson Bay House

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

$280

Very Good (2 reviews)

Inquire

from $280 / night

1 / 30

Simpson Bay Apartment

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

from $216 / night

1 / 20

Simpson Bay Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

from $414 / night

1 / 23

Simpson Bay Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

from $411 / night

1 / 18

Simpson Bay Apartment

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children

from $280 / night

Your search has been expanded 2 miles to include more rentals

1 / 20

St. Maarten-St. Martin Apartment - 0.4 miles away

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

from $272 / night

(6)

1 / 19

St. Maarten-St. Martin Apartment - 1.3 miles away

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

$176

Excellent (6 reviews)

Inquire

from $176 / night

(1)

1 / 30

St. Maarten-St. Martin Villa - 1.6 miles away

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$529

Very Good (1 reviews)

Inquire

from $529 / night

1 / 25

St. Maarten-St. Martin Villa - 1.7 miles away

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

from $551 / night

1 / 12

St. Maarten-St. Martin Apartment - 1.7 miles away

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Ask about pets

from $259 / night

1 / 36

St. Maarten-St. Martin House - 1.7 miles away

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

from $400 / night

1 / 10

St. Maarten-St. Martin Villa - 1.8 miles away

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

from $329 / night

1 / 37

St. Maarten-St. Martin Apartment - 1.8 miles away

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

from $359 / night

(3)

1 / 18

St. Maarten-St. Martin Apartment - 1.8 miles away

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

$200

Very Good (3 reviews)

Inquire

from $200 / night

1 / 10

St. Maarten-St. Martin Villa - 1.8 miles away

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

from $329 / night

(1)

1 / 30

St. Maarten-St. Martin Villa - 1.9 miles away

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

$458

Very Good (1 reviews)

Inquire

from $458 / night

1 / 25

St. Maarten-St. Martin Villa - 1.9 miles away

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

from $286 / night

1 / 16

Sandy Ground Apartment - 2 miles away

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

from $193 / night