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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 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

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

Barbados holiday studio rental

St. Lawrence Gap studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £64 / night

£448 / week

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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

Holiday studio with shared pool in Dominican Republic

Cabarete studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £74 / night

£458 - £595 / week

1 / 24

Holiday home in Caribbean

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £83 / night

£567 - £1,143 / week

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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 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 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

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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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 £192 / night

£1,189 / week

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Villa rental in Saint Mary Parish with swimming pool

Rio Nuevo villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £549 / night

£4,480 - £5,440 / week

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Holiday villa with swimming pool in Barbados

Holetown villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Vida Mejor East Pool and Spa” My family and I stayed three weeks at the East Pool Villa and Spa last august whilst on holiday and had a fantastic time! We have always stayed in Holetown as it has everything you need and we like the area very much. We have previously stayed in studio apartments and hotel apartments which have too been in ideal locations, but even though the latter has been situated right on the beach, we have still felt that there has been something missing. We came across Vida Mejor Villas through their website and were very impressed... the private pool being the main selling point for us and on arrival we were not disappointed... it was fantastic! With the added bonus of the spa too made it extra special. The accommodation was superb... clean, light, airy and spacious, but homely, every need is met with the added peace of mind of the properties being very safe and secure. I cannot recommend these villas highly enough! They are in a fantastic location with all amenities; shops, bank, supermarket, beach and bus stop just a couple of minutes' walk away. We felt rest assured that if we ever needed anything that the owner Carlton would be at hand and help us with anything we needed, as too Peggy, who was also fantastic. Whilst we were on holiday it was my daughters 13th birthday and Carlton had organised for a big, beautiful birthday cake to be delivered on the day!! Which was a wonderful surprise and very thoughtful, and too which made the day that more special. Our highlight would have to be having your own home from home, in particular the computer with 24hr internet access, flat screen television etc. etc. But above all, having your own pool is amazing, and to which makes such a difference to the whole holiday experience. The property is maintained to a high standard and the exterior including pool is set within beautiful surroundings with ample sun loungers and barbeque. This is all within just a stone's throw away from all you would expect from beautiful Barbados!!

from £256 / night

£1,646 - £2,286 / week

1 / 15

Holiday villa with swimming pool in Caribbean

Holetown villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

“Barbados Reunion” We planned our family reunion (4 couples and a 3 year old) for 2 weeks in villas 3 and 4 and had the best time ever. Lots of space and very private. Peggy kept the place neat and clean and Terry made sure the pool was clear and fresh every day. Carlton made sure everything was just right and the security he has installed is the absolute best. The people in Barbados are the friendliest, nicest people we have met throughout the Caribbean. Supermarket and restaurants are within walking distance - be prepared to spend the usual island premium for imported food. We rented an 8 seater van from DriveMatic - they delivered and picked up as promised and with a smile. This allowed us to tour the island some - the roads are good and the drivers are super-polite. In our 2 weeks it rained for all of 30 seconds - we had intermittent clouds most days but these passed by quickly enough. Villas all have AC so at night if needed we could cool things down. Beach is a short walk away - it is not that big and wave action was a little high - so our 3 year old spent a lot of time in the two pools at the villas. We visited Carlisle Bay a couple of times where the beach is fantastic and the ocean shallow - great for kids. We also rode the local buses - the blue ones are run by the government and the yellow ones are privately owned competition. They both charge the same amount (B$1.50) and both are driven very fast - an experience not to be missed! For bird watchers the villas have constant visitors - humming birds, doves, bananaquits, bullfinches etc. And let's not forget the monkeys - just up the road is a plant nursery where a whole bunch of monkeys can be seen - also they come down the road every day to feed on the local trees. All in all we believe the villas were the best value around - hotel rates in Holetown are through the roof, and frankly not worth it having seen the properties - they are on the beach however so they win on that score. The villas are a great getaway-place to visit

from £256 / night

£1,646 - £2,286 / week

1 / 14

Caribbean holiday apartment rental

Carolina apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Overall terrific package” Best location, on lovely beach w/ perfect water temp. and no pebbles/shells in water. Gorgeous view. Immaculate, well laid-out unit. All kinds of restaurants nearby. East transportation to Old San Juan -a Must See. Consierge very helpful. We shall return!!

from £228 / night

£1,594 / week

1 / 16

Puerto Rico holiday villa rental

Luquillo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £87 / night

£435 / week

1 / 14

Caribbean holiday villa rental

Coral Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

“Awesome family vacation” This was our second visit to Drakes View and we again enjoyed everything the property has to offer...views, a well equpped kitchen, hot tub and ample space for our 3 generations to be together for Thanksgiving week. In spite of an abnormally rainy week, we made the best of our beach time and enjoyed the views from the villa when we were forced inside. We lovedbeing able to stay overlooking Coral Bay,our favorite side of St. Johns. We explored several new beaches and snorkeling apots. Thanks to the Roberts family and their wonderful concierge team of Dorothy and Fernando.

from £727 / night

£4,846 / week

1 / 19

Apartment rental in Puerto Rico with shared pool

Fajardo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Totally awesome” I stayed at this Condo in Fajardo, PR with my 86 year old mother, brother and his wife. My brother and I took my mom on vacation to her native Island. So, to say the least we were a bit concern on how she would acclimate and if the condo would accommodate her needs. We were totally beyond pleased with the condo's cleanliness, accessibility for her disabled needs such as wide doors, location on the 1st floor with a ramp. It was so easy for her to get around, I was impressed. The location of this condo is so ideal, I was jealous that it wasn't mine. It is located near the most beautiful beaches in PR, a skip & a hop to the Ferry and very safe with security guards at entry point of the condos. The pools were wonderful, geared towards families with children as well, as singles and couples. The fitness center was well kept and safe. I truly can't say enough about this condo. I highly recommend it and I will be staying at this location on my next vacation. It's idea for couples, family and anyone. And, of course my mom's wish was fulfill, she was very happy that she got to go to PR. Oh, I might add that there are 2 medical centers about 7-8 minutes up the street. That even made us more at ease knowing that if mom needed anything it was so close. I like to end with I wish it were mine... however, I Thank the owner for being so generous and sharing his vacation home! I rate it Outstanding!!

from £115 / night

£800 / week

1 / 59

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