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Watersports Holidays in Caribbean - Holiday Lettings

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4,500 properties with watersports onsite or nearby

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Holiday villa with swimming pool in Caribbean

Orient Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £392 / night

£2,741 / week

1 / 24

Caribbean holiday home rental

Las Galeras house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

from £89 / night

£525 / week

1 / 16

Bungalow rental in Caribbean

Le Moule bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £49 / night

£270 / week

1 / 4

Caribbean holiday home rental

Priory house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £37 / night

£196 / week

1 / 16

Holiday villa with swimming pool in Caribbean

Le Marin villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £212 / night

£1,484 / week

1 / 56

Apartment rental in Caribbean

Priory apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £49 / night

£340 / week

1 / 26

Holiday villa in Trinidad and Tobago

Black Rock villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £159 / night

£653 - £3,247 / week

1 / 26

Holiday apartment accommodation

Grand Anse apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £168 / night

£1,174 / week

1 / 45

Holiday condo with shared pool, golf nearby in Caribbean

Seven Mile Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £486 / night

£2,276 / week

1 / 21

Caribbean holiday home rental

William's Town house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £287 / night

£2,007 / week

1 / 19

Holiday home with swimming pool, golf nearby in Caribbean

Le Diamant house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £169 / night

£1,180 / week

1 / 4

Holiday villa with swimming pool, golf nearby in Caribbean

Holetown villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 4

from £344 / night

£2,405 / week

1 / 58

Caribbean holiday home rental

Carriacou Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £265 / night

£1,853 / week

1 / 20

Home rental in Guadeloupe with swimming pool

Sainte-Anne house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £73 / night

£482 / week

1 / 23

Apartment rental in Caribbean

Baie-Mahault apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £63 / night

£376 / week

1 / 18

Holiday apartment in Caribbean

Cruz Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £278 / night

£1,946 / week

1 / 23

Holiday studio with shared pool, golf nearby in Guadeloupe

Saint Francois studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £77 / night

£540 / week

1 / 21

Anguilla holiday villa rental

Shoal Bay Village villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £728 / night

£5,095 / week

1 / 65

Caribbean holiday apartment rental

Aguadilla apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £164 / night

£1,059 - £1,491 / week

1 / 35

Caribbean holiday home rental

Las Terrenas house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £39 / night

£270 / week

1 / 95

Holiday apartment with golf nearby in Aruba

Noord apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £146 / night

£1,019 / week

1 / 20

Holiday apartment with golf nearby in Caribbean

Noord apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £146 / night

£1,019 / week

1 / 17

Holiday private room rental

Bayahibe private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £44 / night

£261 / week

1 / 20

Holiday home rental

Le Carbet house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £77 / night

£434 / week

1 / 25

Holiday villa with swimming pool, golf nearby in Dominican Republic

Puerto Plata villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £164 / night

£1,147 / week

1 / 19

Holiday villa with swimming pool in Caribbean

Las Galeras villa

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 10

from £221 / night

£1,544 / week

1 / 63

Holiday apartment in St. Vincent and the Grenadines

Clifton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £80 / night

£556 / week

1 / 24

Holiday yacht in Caribbean

Nassau yacht

  • 6 bedrooms
  • 2 bathrooms
  • sleeps 12

from £214 / night

£1,496 - £116,631 / week

1 / 17

Holiday home with swimming pool in Caribbean

Willemstad house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £530 / night

£3,705 / week

1 / 34

Condo rental in Bahamas

Freeport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £101 / night

£706 / week

1 / 8

Holiday home with swimming pool in Aruba

Noord house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from £309 / night

£2,162 / week

1 / 20

Holiday villa in Caribbean

Kralendijk villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £70 / night

£488 / week

1 / 14

Holiday villa in Caribbean

Kralendijk villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £57 / night

£396 / week

1 / 12

Holiday villa rental

Kralendijk villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £48 / night

£334 / week

1 / 13

Holiday studio in Bonaire

Kralendijk studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £94 / night

£655 / week

1 / 6

Holiday apartment with shared pool in Caribbean

Puerto Plata apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £119 / night

£838 / week

1 / 14

Caribbean holiday home rental

Le Robert house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £139 / night

£897 - £1,221 / week

1 / 21

Holiday studio with shared pool in Dominican Republic

Cabarete studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £71 / night

£441 - £574 / week

1 / 24

Holiday villa with swimming pool, golf nearby in Guadeloupe

Saint Francois villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £371 / night

£2,415 - £2,765 / week

1 / 19

Studio rental in Caribbean with shared pool

Cabarete studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £75 / night

£486 / week

1 / 23

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