50 Best Simpson Bay Villas on Holiday Lettings - Vacation rentals

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Simpson Bay

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191 Vacation rentals

Travelers going to Simpson Bay are booking March 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 $419 / night

$2855 / week

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from $419 / 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 $169 / night

$1183 - $1393 / week

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from $169 / night

29

Sint Maarten / Simpson Bay

Studio 6 4 nights min

  • Studio
  • Sleeps 6
  • 4 nights min
  • Ask about children

 …see more

from $343 / night

$2400 - $3000 / week

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from $343 / night

39

Sint Maarten / Simpson Bay

5 10 Min stay varies

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

 …see more

from $571 / night

$4000 - $13500 / week

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from $571 / 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 $786 / night

$5500 - $7500 / week

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from $786 / 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 $485 / night

$3350 - $9060 / week

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from $485 / 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

$1800 - $3600 / week

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from $258 / night

(1) Excellent 

12

Sint Maarten / Simpson Bay

5 10 Min stay varies

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

 …see more

from $457 / night

$3200 - $7900 / week

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from $457 / night

(2) Very Good 

34

Sint Maarten / Simpson Bay

3 6 Min stay varies

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

 …see more

from $458 / night

$3206 - $7504 / week

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from $458 / night

13

Sint Maarten / Simpson Bay

3 6 Min stay varies

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

 …see more

from $729 / night

$5103 - $6503 / week

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from $729 / 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 $858 / night

$6000 - $11900 / week

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from $858 / 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

$1800 - $3600 / week

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from $258 / night

22

Sint Maarten / Simpson Bay

5 2 Min stay varies

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

 …see more

from $843 / night

$5900 - $14000 / week

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from $843 / 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 $315 / night

$2205 - $5900 / week

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from $315 / 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

$1900 - $3500 / week

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from $272 / night

25

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 $543 / night

$3800 - $7500 / week

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from $543 / night

(9) 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 $240 / night

$1600 - $3900 / week

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from $240 / 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 $358 / night

$2500 - $6000 / week

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from $358 / night

22

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from $285 / night

$2000 - $4000 / week

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from $285 / 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 $340 / night

$2380 - $4500 / week

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from $340 / 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 $642 / night

$4500 - $14000 / week

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from $642 / night

33

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $543 / night

$3800 - $5200 / week

Inquire View

from $543 / night

25

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from $257 / night

$1800 - $3600 / week

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from $257 / 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 $215 / night

$1505 - $2450 / week

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from $215 / night

23

Sint Maarten / Simpson Bay

2 4 Min stay varies

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

 …see more

from $314 / night

$2200 - $5900 / week

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from $314 / night

48

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 $500 / night

$3500 - $11900 / week

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from $500 / 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 $643 / night

$4500 - $14000 / week

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from $643 / night

(1) Excellent 

15

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 $415 / night

$2900 - $5900 / week

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from $415 / 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 $336 / night

$2352 - $4004 / week

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from $336 / 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 $600 / night

$4200 - $28000 / week

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from $600 / night

10

Sint Maarten / Simpson Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Suitable for children age 5+

 …see more

from $536 / night

$3750 - $6500 / week

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from $536 / 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 $1400 / night

$8400 - $25200 / week

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from $1400 / 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

$2400 - $4200 / week

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from $343 / 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 $144 / night

$1008 / week

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from $144 / 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

$1600 - $2600 / week

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from $229 / night

(2) 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 $326 / night

$2280 - $4500 / week

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from $326 / night

25

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

$1800 - $3500 / week

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from $258 / night

21

Sint Maarten / Simpson Bay

5 10 Min stay varies

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

 …see more

from $142 / night

$1000 - $25000 / 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 $214 / night

$1500 - $1600 / week

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from $214 / night

20

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

$2900 - $3700 / week

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from $414 / night