50 Best Simpson Bay Villas on Holiday Lettings - Vacation rentals

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Simpson Bay

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206 Vacation rentals

Travelers going to Simpson Bay are booking February dates now. Secure your vacation rental today and have the perfect trip.

23

Simpson Bay / Simpson Bay Beach

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

 …see more

from $423 / night

$2881 / week

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from $423 / night

(3) Excellent 

24

Sint Maarten / Simpson Bay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $489 / night

$3378 - $9134 / week

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from $489 / night

(1) Excellent 

31

Sint Maarten / Simpson Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $850 / night

$5948 - $14114 / week

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from $850 / night

(2) Very Good 

32

Sint Maarten / Simpson Bay

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from $146 / night

$1017 / week

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from $146 / night

(26) Excellent 

12

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $171 / night

$1193 - $1405 / week

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from $171 / night

33

Sint Maarten / Simpson Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $1412 / night

$9880 - $25405 / week

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from $1412 / night

(2) Excellent 

12

Simpson Bay / Simpson Bay Beach

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Air conditioning

 …see more

from $113 / night

$786 / week

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from $113 / night

(1) Excellent 

32

Sint Maarten / Simpson Bay

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly

 …see more

from $849 / night

$5948 - $8973 / week

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from $849 / night

26

Sint Maarten / Simpson Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $858 / night

$6001 - $11900 / week

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from $858 / night

(2) Very Good 

24

Simpson Bay / Simpson Bay Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $362 / night

$2521 - $6039 / week

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from $362 / night

21

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $202 / night

$1412 - $2521 / week

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from $202 / night

(1) Excellent 

34

Simpson Bay / Simpson Bay Beach

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $303 / night

$2118 / week

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from $303 / night

25

Sint Maarten / Simpson Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly

 …see more

from $288 / night

$2017 - $3025 / week

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from $288 / night

(1) Excellent 

61

Sint Maarten / Simpson Bay

6 12 Min stay varies

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

 …see more

from $1815 / night

$12703 - $28228 / week

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from $1815 / night

14

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly

 …see more

from $152 / night

$1059 / week

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from $152 / night

9

Sint Maarten / Simpson Bay

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

 …see more

from $163 / night

$1137 / week

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from $163 / night

10

Sint Maarten / Simpson Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $793 / night

$5545 - $7561 / week

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from $793 / night

(2) Excellent 

20

Sint Maarten / Simpson Bay

2 4 7 nights min

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

 …see more

from $216 / night

$1513 - $1614 / week

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from $216 / night

33

Sint Maarten / Simpson Bay

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $227 / night

$1765 / week

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from $227 / night

26

Sint Maarten / Simpson Bay

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly

 …see more

from $864 / night

$6049 - $7864 / week

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from $864 / night

20

Simpson Bay / Simpson Bay Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $217 / night

$1518 - $3113 / week

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from $217 / night

23

Sint Maarten / Simpson Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

 …see more

from $605 / night

$4235 / week

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from $605 / night

11

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $341 / night

$2381 - $4500 / week

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from $341 / night

35

Sint Maarten / Simpson Bay

5 10 Min stay varies

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

 …see more

from $792 / night

$5545 - $13106 / week

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from $792 / night

28

Sint Maarten / Simpson Bay

5 10 Min stay varies

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

 …see more

from $850 / night

$5949 - $14114 / week

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from $850 / night

(8) Excellent 

22

Sint Maarten / Simpson Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $242 / night

$1614 - $2823 / week

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from $242 / night

38

Sint Maarten / Simpson Bay

5 10 Min stay varies

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

 …see more

from $656 / night

$4587 - $28228 / week

Inquire View

from $656 / night

(1) Excellent 

14

Sint Maarten / Simpson Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $375 / night

$2622 / week

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from $375 / night

22

Simpson Bay / Simpson Bay Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $217 / night

$1518 - $3113 / week

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from $217 / night

25

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $548 / night

$3831 - $7561 / week

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from $548 / night

10

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $71 / night

$494 / week

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from $71 / night

13

Sint Maarten / Simpson Bay

3 6 Min stay varies

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

 …see more

from $361 / night

$2521 - $6049 / week

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from $361 / night

22

Simpson Bay / Simpson Bay Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $217 / night

$1518 - $3113 / week

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from $217 / night

(5) Very Good 

18

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

29

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $260 / night

$1815 - $3630 / week

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from $260 / night

31

Sint Maarten / Simpson Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $245 / night

$1709 / week

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from $245 / night

(3) Excellent 

33

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $503 / night

$2980 - $6856 / week

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from $503 / night

22

Sint Maarten / Simpson Bay

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $375 / night

$2622 / week

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from $375 / night

29

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Suitable for children age 5+

 …see more

from $217 / night

$1518 - $2118 / week

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from $217 / night

24

Sint Maarten / Simpson Bay

6 12 Min stay varies

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

 …see more

from $1815 / night

$12703 - $28228 / week

Inquire View

from $1815 / night