Villas in Sint Maarten and Houses - Holiday Lettings - Holiday Rentals Sint Maarten

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North America Holidays
172375 properties
Caribbean Holidays
23680 properties
Simpson Bay
178 properties
Philipsburg
153 properties
Oyster Pond
131 properties
Cupecoy Bay
42 properties
Maho
29 properties
Cole Bay
18 properties
Mullet Bay
13 properties
Dawn Beach
11 properties
Beacon Hill, Sint Maarten
5 properties

Sint Maarten

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605 Holiday homes

20

Cupecoy Bay holiday apartment rental

Sint Maarten / Cupecoy Bay

2 4 Min stay varies

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

from £248 / night

£1734 - £2235 / week

Enquire View

from £248 / night

(3) Very Good 

24

Apartment rental in Simpson Bay

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 £231 / night

£1616 - £4608 / week

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from £231 / night

24

Holiday home in Simpson Bay

Sint Maarten / Simpson Bay

2 6 Min stay varies

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

from £199 / night

£1385 - £2924 / week

Enquire View

from £199 / night

24

Holiday villa with shared pool in Philipsburg

Sint Maarten / Philipsburg

5 10 Min stay varies

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

from £605 / night

£4233 / week

Enquire View

from £605 / night

(5) Excellent 

28

Philipsburg holiday apartment rental

Sint Maarten / Philipsburg

1 2 Min stay varies

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

from £38 / night

£264 - £458 / week

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from £38 / night

(1) Very Good 

20

Holiday apartment in Oyster Pond

Sint Maarten / Oyster Pond

3 6 Min stay varies

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

from £276 / night

£1924 - £4616 / week

Enquire View

from £276 / night

23

Holiday villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £660 / night

£4616 - £7231 / week

Enquire View

from £660 / night

(2) Very Good 

31

Holiday villa in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

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

from £385 / night

£2693 - £4847 / week

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from £385 / night

21

Villa rental in Simpson Bay with swimming pool

Sint Maarten / Simpson Bay

3 6 Min stay varies

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

from £275 / night

£1924 - £3847 / week

Enquire View

from £275 / night

(3) Excellent 

24

Pelican Key holiday villa rental

Sint Maarten / Pelican Key

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £193 / night

£1347 / week

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from £193 / night

(2) Excellent 

20

Holiday home rental

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 £165 / night

£1154 / week

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from £165 / night

25

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 £199 / night

£1385 - £2693 / week

Enquire View

from £199 / night

8

Holiday villa in Philipsburg

Sint Maarten / Philipsburg

5 10 Min stay varies

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

from £495 / night

£3463 - £6774 / week

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from £495 / night

22

Condo rental in Cupecoy Bay with shared pool

Sint Maarten / Cupecoy Bay

2 6 3 nights min

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

from £231 / night

£1616 / week

Book View

from £231 / night

(7) Excellent 

22

Holiday villa accommodation

Sint Maarten / Simpson Bay

2 4 Min stay varies

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

from £160 / night

£1116 - £2579 / week

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from £160 / night

15

Villa rental in Oyster Pond with shared pool

Sint Maarten / Oyster Pond

4 8 Min stay varies

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

from £374 / night

£2617 / week

Enquire View

from £374 / night

(2) Excellent 

14

Simpson Bay holiday apartment rental

Sint Maarten / Simpson Bay

2 4 Min stay varies

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

from £295 / night

£2062 - £3462 / week

Enquire View

from £295 / night

21

Holiday villa in Simpson Bay

Sint Maarten / Simpson Bay

1 2 Min stay varies

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

from £154 / night

£1077 - £1924 / week

Enquire View

from £154 / night

24

Holiday villa with shared pool in Philipsburg

Sint Maarten / Philipsburg

4 8 Min stay varies

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

from £550 / night

£3850 / week

Enquire View

from £550 / night

22

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 £199 / night

£1385 - £2770 / week

Enquire View

from £199 / night

(1) Very Good 

24

Holiday villa rental

Sint Maarten / Oyster Pond

3 6 5 nights min

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

from £253 / night

£1766 - £1935 / week

Enquire View

from £253 / night

10

Holiday apartment in Simpson Bay

Sint Maarten / Simpson Bay

2 4 1 night min

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

from £413 / night

£2885 - £5000 / week

Enquire View

from £413 / night

(1) Excellent 

17

Villa rental in Oyster Pond with swimming pool

Sint Maarten / Oyster Pond

4 8 Min stay varies

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

from £243 / night

£1693 - £4616 / week

Enquire View

from £243 / night

(1) Very Good 

24

Apartment rental in Simpson Bay with shared pool

Sint Maarten / Simpson Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £166 / night

£1154 - £1885 / week

Enquire View

from £166 / night

(2) Very Good 

32

Simpson Bay holiday apartment rental

Sint Maarten / Simpson Bay

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £111 / night

£776 / week

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from £111 / night

5

Holiday condo with shared pool in Oyster Pond

Sint Maarten / Oyster Pond

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £292 / night

£2039 / week

Book View

from £292 / night

26

Holiday villa with swimming pool in Simpson Bay

Sint Maarten / Simpson Bay

6 12 Min stay varies

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

from £660 / night

£4616 - £9154 / week

Enquire View

from £660 / night

(2) Very Good 

22

Holiday villa with swimming pool in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

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

from £385 / night

£2693 - £4847 / week

Enquire View

from £385 / night

23

Philipsburg holiday villa rental

Sint Maarten / Philipsburg

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly

from £330 / night

£2310 - £4620 / week

Book View

from £330 / night

(6) Excellent 

40

Apartment rental in Oyster Pond with swimming pool

Sint Maarten / Oyster Pond

3 6 Min stay varies

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

from £424 / night

£2962 - £5770 / week

Enquire View

from £424 / night

(2) Excellent 

13

Holiday apartment in Philipsburg

Sint Maarten / Philipsburg

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary

from £67 / night

£458 / week

Book View

from £67 / night

33

Simpson Bay holiday villa rental

Sint Maarten / Simpson Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

from £418 / night

£2924 - £5770 / week

Enquire View

from £418 / night

5

Holiday apartment in Philipsburg

Sint Maarten / Philipsburg

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £330 / night

£2308 / week

Book View

from £330 / night

13

Holiday apartment with shared pool, golf nearby in Philipsburg

Sint Maarten / Philipsburg

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £231 / night

£1616 - £2154 / week

Book View

from £231 / night

(5) Excellent 

50

Condo rental in Philipsburg with shared pool

Sint Maarten / Philipsburg

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Air conditioning

from £69 / night

£458 - £749 / week

Book View

from £69 / night

13

Holiday villa in Philipsburg

Sint Maarten / Philipsburg

3 6 Min stay varies

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

from £220 / night

£1540 - £2693 / week

Book View

from £220 / night

7

Holiday studio in Cupecoy Bay

Sint Maarten / Cupecoy Bay

Studio 2 7 nights min

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

from £94 / night

£654 / week

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from £94 / night

(3) Excellent 

24

Oyster Pond holiday farmhouse rental

Sint Maarten / Oyster Pond

3 6 Min stay varies

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

from £276 / night

£1924 - £4616 / week

Enquire View

from £276 / night

(3) Average 

21

Simpson Bay holiday villa rental

Sint Maarten / Simpson Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

from £231 / night

£1616 - £2693 / week

Book View

from £231 / night

(2) Excellent 

13

Holiday private room in Cupecoy Bay

Sint Maarten / Cupecoy Bay

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £116 / night

£693 - £1231 / week

Book View

from £116 / night

1