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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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Holiday villa with swimming pool in Westmoreland Parish

Little Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from £321 / night

£2,291 / week

1 / 27

Caribbean holiday b&b rental

Little Bay b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £120 / night

£734 / week

1 / 23

Caribbean holiday apartment rental

Vieux-Habitants apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £175 / night

£1,225 / week

1 / 22

Caribbean holiday apartment rental

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £65 / night

£449 / week

1 / 19

Holiday b&b in Caribbean

Cabarete b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £197 / night

£1,375 / 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

£1,084 / week

1 / 33

Holiday apartment rental

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £420 / night

£2,940 / week

1 / 8

Apartment rental in Caribbean

Santo Domingo apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

from £82 / night

£571 / week

1 / 42

Caribbean holiday apartment rental

Santo Domingo apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 3

from £87 / night

£610 / 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

Barbados holiday studio rental

St. Lawrence Gap studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £65 / night

£449 / 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 £65 / night

£449 / week

1 / 22

Holiday villa in Saint Ann Parish

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £229 / night

£1,604 / week

1 / 34

Villa rental in Barbados

Dover villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £392 / night

£2,646 / week

1 / 23

Holiday apartment in Caribbean

Santo Domingo Este apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £37 / night

£257 / week

1 / 16

Holiday apartment in St. Vincent and the Grenadines

Clifton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £83 / night

£578 / week

1 / 24

Apartment accommodation in Caribbean

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £65 / night

£326 - £582 / 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

£961 / week

1 / 21

Holiday studio with shared pool in Dominican Republic

Cabarete studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £74 / night

£459 - £596 / week

1 / 24

Holiday home in Caribbean

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £83 / night

£569 - £1,146 / 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

£635 / week

1 / 17

Kingston Parish holiday apartment rental

Kingston apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £138 / night

£963 / week

1 / 29

Holiday studio with shared pool in Caribbean

Grace Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £138 / night

£1,746 / week

1 / 17

Holiday villa in Caribbean

Kralendijk villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £173 / night

£1,208 / week

1 / 31

Holiday guest house in Caribbean

Crown Point guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £74 / night

£514 / week

1 / 31

Holiday home with shared pool in Caribbean

Ocho Rios house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £184 / night

£1,283 / week

1 / 39

Holiday home in Caribbean

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £60 / night

£417 / 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

£494 / week

1 / 5

Holiday apartment with shared pool, golf nearby in Caribbean

Punta Cana apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £274 / night

£1,650 / week

1 / 23

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

£779 - £1,100 / week

1 / 26

Holiday home in Aruba

Oranjestad house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Great vacation home!” Simply amazing house and owners!!!The house has everything u need. Mrs and Mr Odor were very helpful and made sure that we have all thad needed for our vacation! Thank you, We will be back soon!

from £87 / night

£610 - £995 / week

1 / 29

Villa rental in Trinidad and Tobago with swimming pool

Prospect villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Home away from Home” Amazing experience at Villa Nirvana. The service was impeccable. The owners called frequently to ensure the stay was going well and they are very understanding people. There was a cleaner that came in everyday and all amenities were provided. The villa has all the comforts of a house and an amazing pool which is great for after a long day at the beach. The rooms are spacious and the view from each room of the Buccoo Reef was amazing.We loved the privacy of the place and the lovely peaceful atmosphere. The location is ideal being away from all the hustle and bustle of Bon accord, however is still close to some gorgeous beaches. If there was one thing that could be worked on is the maid service daily I guess depending on the people, and if they would like the service everyday. However, for us with the maid coming everyday it was a bit much. Overall though, the entire experience was amazing and we would recommend and return to Villa Nirvana in a heartbeat!

from £193 / night

£1,192 / week

1 / 28

Apartment accommodation in Caribbean

San Juan apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £175 / night

£1,097 / week

1 / 31

Villa rental in Saint Mary Parish with swimming pool

Rio Nuevo villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £688 / night

£4,491 - £5,453 / week

1 / 67

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