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Family Friendly Holidays in Caribbean - Holiday Lettings

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15,753 family friendly properties

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Holiday home with golf nearby in Jamaica

Montego Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £94 / night

£656 / week

1 / 33

Holiday villa in Guadeloupe

Saint Francois villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £77 / night

£542 / week

1 / 16

Holiday villa with swimming pool in Guadeloupe

Saint Francois villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £109 / night

£759 / week

1 / 20

Holiday villa in Caribbean

Saint Francois villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £123 / night

£858 / week

1 / 24

Caribbean holiday villa rental

Juan Dolio villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £216 / night

£1,037 - £1,128 / week

1 / 11

Holiday villa with swimming pool, golf nearby in Caribbean

Saint Francois villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £196 / night

£1,373 / week

1 / 30

Holiday villa in Bahamas

Windemere Island villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

from £871 / night

£6,092 / week

1 / 12

Holiday apartment with shared pool in Dominican Republic

Juan Dolio apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £138 / night

£962 / week

1 / 10

Holiday home in Caribbean

Trois-Ilets house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £104 / night

£725 / week

1 / 18

Puerto Rico holiday boathouse rental

San Juan boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £124 / night

£642 / week

1 / 28

Caribbean holiday apartment rental

Ocho Rios apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £111 / night

£776 / week

1 / 10

Dominican Republic holiday b&b rental

Bavaro b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

from £21 / night

£119 / week

1 / 19

Holiday private room rental

Puerto Plata private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £101 / night

£706 / week

1 / 12

Holiday villa with swimming pool in Jamaica

Montego Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £161 / night

£1,100 / week

1 / 29

Holiday villa in Caribbean

Five Islands Village villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £71 / night

£494 / week

1 / 5

Holiday apartment rental

Argyle apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £67 / night

£468 / week

1 / 11

Holiday b&b with shared pool in Caribbean

Bavaro b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £28 / night

£170 / week

1 / 23

Holiday home with swimming pool in Caribbean

Santiago de los Caballeros house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 27

from £362 / night

£2,533 / week

1 / 143

Holiday home in Caribbean

Cruz Bay house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £303 / night

£2,116 / week

1 / 10

Holiday home with golf nearby in Caribbean

Rio Grande house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £504 / night

£3,527 / week

1 / 36

Holiday villa with swimming pool in Caribbean

Puerto Plata villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £212 / night

£1,478 / week

1 / 16

Holiday villa with swimming pool in Caribbean

Ocho Rios villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £715 / night

£5,002 / week

1 / 27

Holiday condo in Bahamas

Nassau condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £275 / night

£1,924 / week

1 / 19

Holiday apartment with shared pool, golf nearby in Caribbean

Punta Cana apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £274 / night

£1,649 / week

1 / 23

Dominican Republic holiday villa rental

Rio San Juan villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £156 / night

£1,090 / week

1 / 18

Dominican Republic holiday home rental

Las Galeras house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

from £385 / night

£2,424 - £2,681 / week

1 / 21

Caribbean holiday home rental

Las Galeras house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

from £92 / night

£545 / week

1 / 16

Caribbean holiday boathouse rental

San Juan boathouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £550 / night

£3,847 / week

1 / 7

Caribbean holiday home rental

Priory house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £38 / night

£204 / week

1 / 16

Holiday studio with shared pool in Caribbean

Punta Cana studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £138 / night

£916 / week

1 / 11

Holiday villa with swimming pool in Caribbean

Le Marin villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £217 / night

£1,518 / week

1 / 56

Apartment rental in Caribbean

Priory apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £51 / night

£353 / week

1 / 26

Dominican Republic holiday condo rental

Puerto Plata condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £115 / night

£802 / week

1 / 14

Holiday apartment in Caribbean

Cabarete apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £51 / night

£353 / week

1 / 67

Caribbean holiday home rental

Enterprise house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £147 / night

£1,026 / week

1 / 19

Holiday villa in Trinidad and Tobago

Black Rock villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £165 / night

£678 - £3,371 / week

1 / 26

Villa accommodation in Caribbean

Orange Bay villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £83 / night

£468 / week

1 / 28

Holiday condo with shared pool, golf nearby in Caribbean

Seven Mile Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £504 / night

£2,364 / week

1 / 21

Curaçao holiday villa rental

Tera Kora villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £99 / night

£690 - £1,104 / week

1 / 26

Home rental in Caribbean with shared pool, golf nearby

Portmore house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £83 / night

£520 / week

1 / 9

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