50 Best Simpson Bay Villas on Holiday Lettings - Vacation rentals

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Simpson Bay

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197 Vacation rentals

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23

Simpson Bay Vacation home rental

Simpson Bay / Simpson Bay Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Perfect location between Simpson Bay & Philipsburg,in the new gated community of"Indigo Bay Beach". This brand new exquisite residence, very well modern decorated & equipped. Beautiful living area, lots of glass doors that open to a private pool, wrapp  …see more

from $426 / night

$2901 / week

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from $426 / 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 $121 / night

$847 - $1405 / week

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from $121 / night

(1)  

15

Sint Maarten / Simpson Bay

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Car not necessary

 …see more

from $323 / night

$2258 / week

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from $323 / night

(2) Excellent 

12

Simpson Bay / Simpson Bay Beach

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Suitable for children age 5+

 …see more

from $114 / night

$792 / week

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from $114 / night

(3) Excellent 

19

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $415 / night

$2901 - $5900 / week

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from $415 / 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 $1801 / night

$12601 - $28000 / week

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from $1801 / night

15

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Ask about pets

 …see more

from $252 / night

$1764 / week

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from $252 / night

30

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

$12700 - $28223 / week

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from $1815 / night

(2) Good 

29

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $229 / night

$1601 - $2600 / week

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from $229 / night

(1) Excellent 

10

Simpson Bay / Simpson Bay Beach

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Air conditioning

 …see more

from $353 / night

$2515 / week

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from $353 / 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

$1764 / week

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from $227 / night

(1) Excellent 

14

Sint Maarten / Simpson Bay

2 4 Min stay varies

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

 …see more

from $258 / night

$1801 - $3601 / week

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from $258 / night

26

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 $865 / night

$6054 - $11995 / week

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from $865 / night

10

Sint Maarten / Simpson Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $536 / night

$3751 - $6500 / week

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from $536 / night

(4) Excellent 

43

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

$5947 - $14112 / week

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from $850 / night

(1) Excellent 

14

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $383 / night

$2680 - $4500 / week

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from $383 / night

(1) Excellent 

31

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $343 / night

$2401 - $4201 / week

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from $343 / night

(6) Excellent 

22

Sint Maarten / Simpson Bay

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $242 / night

$1613 - $3528 / week

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from $242 / night

(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 $258 / night

$1801 - $3601 / week

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from $258 / night

41

Sint Maarten / Simpson Bay

5 10 Min stay varies

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

 …see more

from $1153 / night

$8064 - $18143 / week

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from $1153 / night

22

Sint Maarten / Simpson Bay

2 4 Min stay varies

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

 …see more

from $258 / night

$1801 - $3601 / week

Inquire View

from $258 / 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 $843 / night

$5900 - $14000 / week

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from $843 / 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

(2) Excellent 

25

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 $540 / night

$3629 - $9334 / week

Book View

from $540 / night

(7) Excellent 

22

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $244 / night

$1701 - $3900 / week

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from $244 / 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 $142 / night

$988 / week

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from $142 / 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

$1512 - $1764 / week

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from $216 / night

(3) Very Good 

13

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $398 / night

$2780 - $4500 / week

Inquire View

from $398 / night

(1) Excellent 

23

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 $279 / night

$1950 - $4000 / week

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from $279 / night

40

Sint Maarten / Simpson Bay

5 10 Min stay varies

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

 …see more

from $779 / night

$5443 - $11592 / week

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from $779 / night

22

Simpson Bay / Simpson Bay Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly

 …see more

from $217 / night

$1517 - $4085 / week

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from $217 / night

24

Sint Maarten / Simpson Bay

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $543 / night

$3801 / week

Inquire View

from $543 / night

(5) Excellent 

17

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool

 …see more

from $252 / night

$1512 - $3528 / week

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from $252 / night

61

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 $634 / night

$4438 - $8573 / week

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from $634 / night

23

Sint Maarten / Simpson Bay

3 6 Min stay varies

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

 …see more

from $414 / night

$2893 - $4939 / week

Inquire View

from $414 / night

20

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $272 / night

$1901 - $3501 / week

Inquire View

from $272 / night

29

Sint Maarten / Simpson Bay

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Ask about children

 …see more

from $344 / night

$2401 - $3001 / week

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from $344 / night

23

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 $864 / night

$6048 - $11995 / week

Inquire View

from $864 / night

(1) Excellent 

32

Sint Maarten / Simpson Bay

5 10 Min stay varies

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

 …see more

from $842 / night

$5900 - $14000 / week

Inquire View

from $842 / night

61

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 $634 / night

$4438 - $8573 / week

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from $634 / night