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Watersports Holidays in Sint Maarten - Holiday Lettings

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89 properties with watersports onsite or nearby

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Holiday villa rental

Cole Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £493 / night

£3,272 - £3,855 / week

1 / 28

Penthouse rental in Oyster Pond with shared pool

Oyster Pond penthouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £384 / night

£2,685 / week

1 / 15

Holiday villa with swimming pool, golf nearby in Maho

Maho villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £672 / night

£4,702 - £9,399 / week

1 / 76

Cupecoy Bay holiday apartment rental

Cupecoy Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £314 / night

£1,879 - £5,480 / week

1 / 40

Holiday villa with swimming pool, golf nearby in Cupecoy Bay

Cupecoy Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £895 / night

£6,263 - £18,006 / week

1 / 24

Holiday apartment in Cole Bay

Cole Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £121 / night

£847 / week

1 / 41

Private room rental in Simpson Bay

Simpson Bay private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £135 / night

£943 / week

1 / 6

Holiday apartment with shared pool in Oyster Pond

Oyster Pond apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Pricing unknown

1 / 11

Holiday condo in Dawn Beach

Dawn Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £385 / night

£2,690 / week

1 / 19

Holiday private room in Simpson Bay

Simpson Bay private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £108 / night

£754 / week

1 / 9

Holiday apartment with shared pool in Oyster Pond

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £390 / night

£2,729 / week

1 / 10

Simpson Bay holiday condo rental

Simpson Bay condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £238 / night

£1,663 / week

1 / 13

Oyster Pond holiday condo rental

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £250 / night

£1,751 / week

1 / 17

Holiday villa with swimming pool, golf nearby in Cupecoy Bay

Cupecoy Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,287 / night

£9,003 - £29,749 / week

1 / 24

Home rental in Oyster Pond with swimming pool

Oyster Pond house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £671 / night

£4,691 - £9,399 / week

1 / 24

Philipsburg holiday apartment rental

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £410 / night

£2,869 / week

1 / 12

Apartment rental in Dawn Beach with shared pool

Dawn Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £341 / night

£2,388 / week

1 / 10

Holiday villa with golf nearby in Beacon Hill, Sint Maarten

Beacon Hill, Sint Maarten villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £990 / night

£6,927 - £18,791 / week

1 / 24

Simpson Bay holiday apartment rental

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £233 / night

£1,632 / week

1 / 10

Holiday villa in Upper Prince's Quarter

Upper Prince's Quarter villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £493 / night

£3,445 - £5,480 / week

1 / 49

Holiday condo rental

Oyster Pond condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £513 / night

£3,586 / week

1 / 30

Holiday villa rental

Mullet Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,015 / night

£4,618 - £16,935 / week

1 / 48

Simpson Bay holiday apartment rental

Simpson Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £206 / night

£1,437 / week

1 / 19

Holiday apartment in Oyster Pond

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £769 / night

£5,379 / week

1 / 20

Villa rental in Oyster Pond with swimming pool

Oyster Pond villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £372 / night

£2,603 - £5,206 / week

1 / 23

Simpson Bay holiday condo rental

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £172 / night

£1,199 / week

1 / 13

Holiday condo with shared pool in Simpson Bay

Simpson Bay condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £280 / night

£1,958 - £3,288 / week

1 / 24

Holiday apartment in Simpson Bay

Simpson Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £180 / night

£1,257 / week

1 / 11

Holiday studio in Oyster Pond

Oyster Pond studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £74 / night

£546 / week

1 / 12

Holiday condo with shared pool in Oyster Pond

Oyster Pond condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £282 / night

£1,973 - £3,054 / week

1 / 55

Holiday villa in Cupecoy Bay

Cupecoy Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £638 / night

£4,461 - £12,133 / week

1 / 24

Holiday villa in Simpson Bay

Simpson Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,406 / night

£9,839 / week

1 / 36

Holiday apartment with shared pool in Simpson Bay

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £180 / night

£1,253 - £2,740 / week

1 / 29

Home rental in Simpson Bay with swimming pool

Simpson Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £169 / night

£1,175 - £2,897 / week

1 / 29

Holiday home with swimming pool in Cupecoy Bay

Cupecoy Bay house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“What a way to get away!” What a setting! If you have ever wanted a beachfront view, a semi private beach with 10 step access and a spacious villa with all of the amenities, this one is for you! It was my first trip to the Island and I can't wait to get back. Staying anywhere else would be a disappointment. Hotels or resorts can not compete with this location. The ultimate in privacy and intimacy. This setting is right out of the movies. A "can't miss".

from £533 / night

£3,727 - £12,056 / week

1 / 35

Holiday condo in Simpson Bay

Simpson Bay condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £155 / night

£1,080 / week

1 / 16

Villa rental in Oyster Pond with swimming pool

Oyster Pond villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £466 / night

£2,795 - £5,206 / week

1 / 34

Philipsburg holiday condo rental

Philipsburg condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £461 / night

£3,227 / week

1 / 6

Holiday villa in Philipsburg

Philipsburg villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £167 / night

£1,164 - £1,259 / week

1 / 17

Holiday condo with shared pool in Pointe Blanche

Pointe Blanche condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £208 / night

£1,453 - £3,151 / week

1 / 15

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