Search 105,200+ Vacation Rentals

Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 36 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

36 Vacation rentals

Filters applied: 4 Bedrooms

1 / 26

Simpson Bay Villa

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

from $643 / night

1 / 16

Simpson Bay Villa

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

from $572 / night

1 / 10

Simpson Bay Villa

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

from $787 / night

1 / 22

Simpson Bay Villa

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

from $572 / night

1 / 30

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $657 / night

1 / 10

Simpson Bay Villa

  • 5
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1071

Inquire

from $1071 / night

(1)

1 / 31

Simpson Bay Villa

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

$843

Excellent (1 reviews)

Inquire

from $843 / night

1 / 28

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

from $614 / night

1 / 7

Simpson Bay Villa

  • 5
  • 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1430

Inquire

from $1430 / night

(5)

1 / 43

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$843

Excellent (5 reviews)

Inquire

from $843 / night

1 / 38

Simpson Bay House

  • 5
  • 10
  • Min stay varies
  • Child friendly
  • Air conditioning

from $650 / night

1 / 26

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children

Inquire for Rates

Inquire

Pricing unknown

1 / 34

Simpson Bay Villa

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

$787

Book

from $787 / night

1 / 40

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

Inquire for Rates

Inquire

Pricing unknown

1 / 21

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly

from $850 / night

1 / 41

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$1143

Inquire

from $1143 / night

1 / 10

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

$1072

Inquire

from $1072 / night

1 / 26

Simpson Bay Villa

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

from $750 / night

1 / 28

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $843 / night

1 / 23

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from $615 / night

1 / 34

Simpson Bay Villa

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

from $787 / night

1 / 22

Simpson Bay Villa

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

from $843 / night

1 / 14

Simpson Bay Villa

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

from $850 / night

1 / 50

Simpson Bay Villa

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1165

Inquire

from $1165 / night

1 / 22

Simpson Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $700 / night

1 / 26

Simpson Bay Villa

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

from $858 / night

1 / 48

Simpson Bay Villa

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

from $750 / night

1 / 46

Simpson Bay Villa

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

from $572 / night

1 / 30

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1800

Inquire

from $1800 / night

1 / 23

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $857 / night

(1)

1 / 39

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$643

Very Good (1 reviews)

Inquire

from $643 / night

1 / 22

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children

$1500

Inquire

from $1500 / night

(1)

1 / 61

Simpson Bay Villa

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

$1800

Excellent (1 reviews)

Inquire

from $1800 / night

1 / 24

Simpson Bay Villa

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1800

Inquire

from $1800 / night

1 / 26

Simpson Bay Villa

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

from $857 / night

1 / 24

Simpson Bay Villa

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

$1800

Inquire

from $1800 / night

Your search has been expanded 1.1 miles to include more rentals

1 / 47

St. Maarten-St. Martin Villa - 1 miles away

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

from $459 / night

1 / 25

St. Maarten-St. Martin Villa - 1.1 miles away

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

$700

Book

from $700 / night

1 / 25

St. Maarten-St. Martin Villa - 1.1 miles away

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

$650

Book

from $650 / night

1 / 24

St. Maarten-St. Martin Villa - 1.1 miles away

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

from $600 / night