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Caribbean Holidays & City Breaks - Holiday Lettings

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1,366 properties suitable for city breaks and holidays

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Caribbean holiday home rental

William's Town house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £298 / night

£2,080 / week

1 / 19

Holiday b&b in Caribbean

Cabarete b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £197 / night

£1,372 / week

1 / 93

Apartment rental in Martinique

Sainte-Anne apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £84 / night

£588 / week

1 / 16

Holiday apartment with shared pool, golf nearby in Caribbean

Rio Grande apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £155 / night

£1,082 / week

1 / 33

Holiday apartment rental

Ocho Rios apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £165 / night

£1,061 - £1,317 / week

1 / 17

Holiday apartment rental

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £420 / night

£2,939 / week

1 / 8

Apartment rental in Caribbean

Santo Domingo apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

from £82 / night

£570 / week

1 / 42

Caribbean holiday apartment rental

Santo Domingo apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

from £87 / night

£608 / week

1 / 45

Holiday apartment in Caribbean

La Romana apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £37 / night

£244 / week

1 / 16

Home rental in Caribbean with swimming pool

Imbert house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

from £43 / night

£264 / week

1 / 16

Holiday home with swimming pool in Bonaire

Kralendijk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £226 / night

£1,577 / week

1 / 41

Barbados holiday studio rental

St. Lawrence Gap studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £64 / night

£448 / week

1 / 14

Studio rental in Caribbean

Le Moule studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £49 / night

£343 / week

1 / 6

Holiday villa in Caribbean

Negril villa

  • 11 bedrooms
  • 13 bathrooms
  • sleeps 24

from £64 / night

£448 / week

1 / 22

Holiday villa in Saint Ann Parish

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £229 / night

£1,600 / week

1 / 34

Villa rental in Barbados

Dover villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £392 / night

£2,645 / week

1 / 23

Holiday apartment in Caribbean

Santo Domingo Este apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £37 / night

£256 / week

1 / 16

Holiday apartment in St. Vincent and the Grenadines

Clifton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £83 / night

£576 / week

1 / 24

Apartment accommodation in Caribbean

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £64 / night

£325 - £581 / week

1 / 34

Holiday apartment in Caribbean

Fort-de-France apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £133 / night

£926 / week

1 / 22

Holiday apartment in Caribbean

Fort-de-France apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £138 / night

£960 / week

1 / 21

Caribbean holiday apartment rental

Aguadilla apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £91 / night

£634 / week

1 / 33

Holiday studio with shared pool in Dominican Republic

Cabarete studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £74 / night

£458 - £595 / week

1 / 24

Holiday villa with swimming pool, golf nearby in Guadeloupe

Saint Francois villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £377 / night

£2,455 - £2,811 / week

1 / 19

Holiday home in Caribbean

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £83 / night

£567 - £1,143 / week

1 / 25

Caribbean holiday apartment rental

Les Abymes apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £21 / night

£144 / week

1 / 6

Holiday home in Dominican Republic

Puerto Plata house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £91 / night

£634 / week

1 / 17

Kingston Parish holiday apartment rental

Kingston apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £138 / night

£960 / week

1 / 29

Holiday studio with shared pool in Dominican Republic

Cabarete studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £51 / night

£197 / week

1 / 24

Holiday studio with shared pool in Caribbean

Grace Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £138 / night

£1,742 / week

1 / 17

Holiday villa in Caribbean

Kralendijk villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £173 / night

£1,207 / week

1 / 31

Holiday home in Saint Catherine Parish

Portmore house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £37 / night

£256 / week

1 / 39

Holiday guest house in Caribbean

Crown Point guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £74 / night

£512 / week

1 / 31

Holiday home with shared pool in Caribbean

Ocho Rios house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £183 / night

£1,280 / week

1 / 39

Holiday home in Caribbean

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £60 / night

£416 / week

1 / 119

Holiday home with golf nearby in Jamaica

Montego Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £93 / night

£652 / week

1 / 33

Holiday villa in Caribbean

Five Islands Village villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £71 / night

£493 / week

1 / 5

Holiday apartment with shared pool, golf nearby in Caribbean

Punta Cana apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £274 / night

£1,646 / week

1 / 23

Holiday apartment rental

Kingston apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £101 / night

£704 / week

1 / 25

Dominica holiday cottage rental

La Plaine cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Sev glorious weeks in a comfortable house, in the pure nature, c” Strongly recommended! In the Mango Stone Cottage I have spent seven wonderful weeks. It is the house that satisfies me as an architect too. It is very well positioned in the surrounding; you are alone, however you feel, that people are not far. The figure of the house is completing the beautiful environment. The concrete structure, stonewalls, open rafters, all made on high level. The interior is a large room and separated bathroom; kitchen is part of the terrace, looking on the river. Large doors opened on the terrace are connecting two spaces and you feel it as your living space. For me comfort ... On the terrace I live: I cook, I eat, read, relax ... from the terrace it is 15 meters into the river, from the same terrace it is about twelve comfortable minutes to the atlantic coast - Bout Sable Beach. And about one minute to the Riverside Café - I love this place with good food, good drink, and good people. I would like to share my best experience. It's authentic text, written directly on the terrace of Mango Stone Cottage, sent from the Riverside Cafe via email to a friend: "I get up at dawn, about half past six. I am not going to the bathroom, flirting with the Taberi River. People are not in sight, so I strip naked, and enters into Taberi River. It is not the hottest, but very OK. It lasts half an hour: adjust the pool on a comfortable lying, and water massages me. After a further slight modification, it works as a countercurrent flow to swim. The head is cleaned from sediments of sleep, the body encouraged. Out from the river, and is clear to me, that one cannot wipe, the goose flesh disappears. With a towel around hips and a banana in hand, I wonder what's next. Come on to take a coffe in the Riverside Cafe, and after to take a bath in warm atlantic waves. But there is a numerous possibilities what to do, I don't know, how to realize it in seven weeks.”

from £133 / night

£778 - £1,098 / week

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