Villas in Simpson Bay and Apartments – Holiday Lettings - Holiday Rentals Simpson Bay

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2,188 Holiday homes

13

Apartment with satellite tv, swimming pool, air conditioning & more in Simpson Bay

Sint Maarten / Simpson Bay

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £311 / night

£2,177 / week

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from £311 / night

(29) Excellent 

14

Fantastic rental in Simpson Bay, Sint Maarten - Great for mountain views and fishing | balcony / terrace

Sint Maarten / Simpson Bay

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £129 / night

£900 - £1,060 / week

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Responds fast!
avg. 2 hours 49 minutes

from £129 / night

40

Holiday apartment in Simpson Bay

Sint Maarten / Simpson Bay

2 4 7 nights min

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

from £434 / night

£3,034 - £3,498 / week

Enquire View

from £434 / night

(2) Excellent 

20

2 bedroom house in Simpson Bay from £163/night | swimming pool & balcony / terrace

Sint Maarten / Simpson Bay

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool

from £163 / night

£1,141 / week

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from £163 / night

(4) Very Good 

12

Holiday accommodation in Simpson Bay Beach with great reviews | air conditioning, patio | water sports

Simpson Bay / Simpson Bay Beach

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Air conditioning

from £94 / night

£654 / week

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Responds fast!
avg. 3 hours 59 minutes

from £94 / night

33

Ideal apartment in Simpson Bay from £171/night | 1 bedroom, sleeps 2, beach / lakeside relaxation

Sint Maarten / Simpson Bay

1 2 7 nights min

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

from £172 / night

£1,334 / week

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from £172 / night

(1) Excellent 

14

Private condo with 1 bedroom in Simpson Bay | bbq, sea view and more

Sint Maarten / Simpson Bay

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies

from £114 / night

£799 / week

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from £114 / night

(2) Very Good 

32

Holiday rental in Simpson Bay with beach / lakeside relaxation, satellite tv

Sint Maarten / Simpson Bay

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £110 / night

£767 / week

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Responds fast!
avg. 2 hours 34 minutes

from £110 / night

(1) Excellent 

29

Self-catering holiday rental in Simpson Bay, Sint Maarten | patio and jacuzzi / hot tub - pet friendly property

Sint Maarten / Simpson Bay

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning

from £326 / night

£2,281 - £2,737 / week

Enquire View

from £326 / night

29

3 bedroom accommodation in Simpson Bay

Sint Maarten / Simpson Bay

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Ask owner if suitable for children

from £260 / night

£1,825 - £4,106 / week

Enquire View

from £260 / night

(16) Excellent 

21

Get this amazing house in Simpson Bay from only £68/night ideal for beach or lakeside relaxation

Sint Maarten / Simpson Bay

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children

from £68 / night

£474 - £714 / week

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from £68 / night

(1) Excellent 

26

Top rated holiday villa in Simpson Bay Beach | beach / lakeside relaxation | Sleeps 4 | water sports | Nearest beach 0.2 km

Simpson Bay / Simpson Bay Beach

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £104 / night

£724 / week

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Responds fast!
avg. 1 hour 21 minutes

from £104 / night

(2) Excellent 

22

Holiday rental in Simpson Bay from £131/night. Sleeps 4, 1 bedroom

Sint Maarten / Simpson Bay

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly

from £131 / night

£916 / week

Book View

from £131 / night

(1) Excellent 

15

Holiday apartment in Simpson Bay, Sint Maarten, from £228/night. With balcony / terrace, sea view and much more!

Sint Maarten / Simpson Bay

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Ask about pets

from £229 / night

£1,597 / week

Book View

from £229 / night

(4) Excellent 

10

Condo rental in Simpson Bay Beach with sea view, wi-fi, golf within 30mins drive from £267/night

Simpson Bay / Simpson Bay Beach

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £267 / night

£1,902 / week

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from £267 / night

(5) Excellent 

28

Apartment in Simpson Bay Beach with garden | fishing, beach or lakeside relaxation & horse riding | From £227/night

Simpson Bay / Simpson Bay Beach

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.01 km
  • Child friendly

from £228 / night

£1,594 - £4,065 / week

Book View

Responds fast!
avg. 2 hours 13 minutes

from £228 / night

(19) Excellent 

Certificate of Excellence

22

Villa in Simpson Bay that has earned great reviews from travellers from £175/night - Perfect for walking holidays

Sint Maarten / Simpson Bay

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £176 / night

£1,144 - £2,134 / week

Book View

Responds fast!
avg. 1 hour 46 minutes

from £176 / night

(1) Excellent 

11

Self-catering apartment in Simpson Bay with swimming pool & satellite tv - Great for beach or lakeside relaxation

Sint Maarten / Simpson Bay

2 3 nights min

  • sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children

from £114 / night

£1,061 / week

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from £114 / night

10

Apartment with 2 bedrooms in Simpson Bay, Sint Maarten | tennis in town, beach / lakeside relaxation & horse riding

Sint Maarten / Simpson Bay

2 4 4 nights min

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

from £198 / night

£1,385 - £2,087 / week

Book View

from £198 / night

(2) Excellent 

23

Sint Maarten - Check out this amazing 1 bedroom condo with staffed property in Simpson Bay

Sint Maarten / Simpson Bay

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly

from £25 / night

£176 / week

Book View

from £25 / night

9

Apartment in Simpson Bay with balcony / terrace from £283/night - Great for walking holidays

Sint Maarten / Simpson Bay

2 6 1 night min

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

from £283 / night

£1,978 / week

Enquire View

from £283 / night

(1) Excellent 

34

Simpson Bay Beach condo great for beach or lakeside relaxation, satellite tv from £228/night

Simpson Bay / Simpson Bay Beach

2 4 6 nights min

  • 2 bedrooms
  • sleeps 4
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £229 / night

£1,597 / week

Book View

from £229 / night

13

Simpson Bay holiday villa rental

Sint Maarten / Simpson Bay

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £435 / night

£3,041 - £4,562 / week

Enquire View

from £435 / night

26

Escape to Simpson Bay, Sint Maarten in this beautiful holiday apartment | Sleeps 6, 3 bedrooms

Sint Maarten / Simpson Bay

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £346 / night

£2,418 / week

Book View

Responds fast!
avg. 2 hours 5 minutes

from £346 / night

(1) Excellent 

61

Holiday villa rental

Sint Maarten / Simpson Bay

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £2,287 / night

£16,006 - £21,341 / week

Enquire View

from £2,287 / night

(3) Excellent 

13

Apartment in Simpson Bay from £228/night | 2 bedrooms, sleeps 4

Sint Maarten / Simpson Bay

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Air conditioning

from £229 / night

£1,597 - £2,130 / week

Book View

from £229 / night

18

Holiday apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £489 / night

£3,422 / week

Enquire View

from £489 / night

(7) Excellent 

23

Spacious self catering property in Simpson Bay | sleeps 8 | nightlife, mountain views

Sint Maarten / Simpson Bay

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.01 km
  • Child friendly

from £304 / night

£2,125 - £6,366 / week

Book View

Responds fast!
avg. 2 hours 13 minutes

from £304 / night

46

Villa rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £1,054 / night

£7,375 / week

Enquire View

from £1,054 / night

22

Holiday villa with swimming pool, golf nearby in Simpson Bay

Sint Maarten / Simpson Bay

5 16 min stay varies

  • 5 bedrooms
  • sleeps 16
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £648 / night

£20,061 - £21,875 / week

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from £648 / night

17

Condo in Simpson Bay Beach with bbq from £392/night - Perfect for beach or lakeside relaxation, water sports & walking holidays

Simpson Bay / Simpson Bay Beach

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Child friendly

from £392 / night

£2,742 / week

Book View

from £392 / night

(3) Excellent 

14

Holiday apartment with shared pool in Simpson Bay

Sint Maarten / Simpson Bay

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £489 / night

£3,422 / week

Enquire View

from £489 / night

23

Enjoy golf within 30mins drive and water sports in Simpson Bay at this condo from £141/night

Sint Maarten / Simpson Bay

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £141 / night

£985 / week

Book View

from £141 / night

(1) Excellent 

14

Holiday apartment in Simpson Bay

Sint Maarten / Simpson Bay

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £391 / night

£2,737 / week

Enquire View

from £391 / night

20

Holiday villa with 2 bedrooms and satellite tv in Simpson Bay

Sint Maarten / Simpson Bay

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Air conditioning

from £185 / night

£1,293 / week

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from £185 / night

22

Stay at this condo in Simpson Bay with wi-fi, satellite tv & swimming pool from £136/night

Sint Maarten / Simpson Bay

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Air conditioning

from £137 / night

£953 / week

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from £137 / night

9

Simpson Bay Beach self-catering condo from £392/night. Pet friendly with satellite tv / beach or lakeside relaxation

Simpson Bay / Simpson Bay Beach

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £392 / night

£2,741 / week

Book View

from £392 / night

13

Experience a home from home at this condo in Simpson Bay | children's pool & garden

Sint Maarten / Simpson Bay

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly

from £99 / night

£609 / week

Book View

Responds fast!
avg. 23 minutes

from £99 / night

17

Condo in Simpson Bay with golf within 30mins drive - from £209/night

Sint Maarten / Simpson Bay

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly

from £210 / night

£1,464 - £2,092 / week

Book View

Responds fast!
avg. 1 hour 0 minutes

from £210 / night

(1) Excellent 

9

Comfortable hotel apartment in Sint Maarten. Sleeps 4 in Simpson Bay

Sint Maarten / Simpson Bay

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children

from £175 / night

£1,213 - £1,480 / week

Book View

from £175 / night