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Jamaica Holidays & City Breaks - Holiday Lettings

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281 properties suitable for city breaks and holidays

Holiday condo with shared pool, golf nearby in Rose Hall

Rose Hall condo

2 bedrooms • 2 bathrooms • sleeps 6

1 review

from £124 / night

£991 / week

1 / 14

Holiday condo with shared pool in Ocho Rios

Ocho Rios condo

1 bedroom • 1 bathroom • sleeps 2

2 reviews

from £51 / night

£352 / week

1 / 34

Ocho Rios holiday apartment let

Ocho Rios apartment

1 bedroom • 1 bathroom • sleeps 3

2 reviews

from £77 / night

£527 / week

1 / 18

Holiday villa accommodation

Discovery Bay villa

7 bedrooms • 7 bathrooms • sleeps 14

2 reviews

from £2,494 / night

£17,451 - £29,084 / week

1 / 26

Runaway Bay holiday guest house rental

Runaway Bay guest house

2 bedrooms • 1 bathroom • sleeps 6

2 reviews

from £126 / night

£962 - £3,527 / week

1 / 19

Holiday guest house in Long Bay

Long Bay guest house

5 bedrooms • 5 bathrooms • sleeps 8

3 reviews

from £57 / night

£377 / week

1 / 27

Kingston holiday apartment rental

Kingston apartment

1 bedroom • 1 bathroom • sleeps 2

1 review

from £58 / night

£401 / week

1 / 13

Holiday condo with shared pool in Ocho Rios

Ocho Rios condo

1 bedroom • 1 bathroom • sleeps 3

“NOT a Club Med experience: exactly what I wanted” I was born and grew up in Kingston, so when my adult daughters wanted to holiday like a local, I looked for a Columbus Heights condominium. Only disadvantage is the long walk to Turtle Beach for which you have to pay a small entrance fee, but I rented a car so we wouldn't have to walk uphill to go "home." I like the architecture and the Jamaican landscaping, the view, the breeze, and being high above the bay. My daughters suffered from the mosquitoes but I think the stinging insects are far worse closer to the beach. Being close to the pool was great to relieve the humid heat without an overdose of tropical sun. I was able to engage a cook for dinners and we went food shopping together in the supermarket and the open air market on day one. Ms Brown is a lovely person and very flexible. Only the bedroom is air-conditioned which ensures a cool restful sleep. Even with the ceiling fans, you may not be comfortable inside the rest of the condo unless a breeze is blowing. The hexagonal open verandah is great except when it rains. So we really felt the vagaries of the weather and were Internet-free for a week, which is what I wanted. Driving on Main Street is a harrowing experience and not recommended for non-Jamaicans. If you walk around and stay out of hotels and hotel restaurants as we did, you will notice the poverty and the grime and you will be stared at and invited to buy many things you may not want. I admit I used my broadest Jamaican accent but even without, you will get better prices if you exchange money and ask to pay in Jamaican dollars. My US-born and bred adult daughters enjoyed the visit and the many conversations with local merchants and service workers, and we all loved the "home-cooked" Jamaican food: escoveitched red snapper, curry goat, roasted breadfruit, stewed oxtail, green bananas, ackee, festival, bammy and more. Guineps were in season and sold on street corners. If you want my kind of holiday and have a sense of humor and an appreciation of natural beauty, this rental will work for you. Janet was very responsive, helpful and a pleasure to deal with.

20 reviews

from £46 / night

£321 / week

1 / 21

Spanish Town holiday home rental

Spanish Town house

3 bedrooms • 1 bathroom • sleeps 4

from £95 / night

£659 / week

1 / 13

Little Bay holiday villa rental

Little Bay villa

3 bedrooms • 2 bathrooms • sleeps 6

from £282 / night

£1,973 / week

1 / 5

Holiday villa in Ocho Rios

Ocho Rios villa

2 bedrooms • 2 bathrooms • sleeps 4

9 reviews

from £377 / night

£2,636 / week

1 / 30

Holiday studio in Ocho Rios

Ocho Rios studio

Studio • 1 bathroom • sleeps 2

6 reviews

from £92 / night

£642 / week

1 / 15

Ocho Rios holiday villa rental

Ocho Rios villa

4 bedrooms • 5 bathrooms • sleeps 10

6 reviews

from £405 / night

£2,830 / week

1 / 29

Holiday apartment in Ocho Rios

Ocho Rios apartment

3 bedrooms • 3 bathrooms • sleeps 8

11 reviews

from £126 / night

£916 / week

1 / 62

Ocho Rios holiday villa rental

Ocho Rios villa

4 bedrooms • 4 bathrooms • sleeps 8

5 reviews

from £292 / night

£2,040 / week

1 / 46

Portmore holiday home rental

Portmore house

1 bedroom • 2 bathrooms • sleeps 6

4 reviews

from £69 / night

£470 / week

1 / 20

St James, Montego Bay holiday villa rental

St James, Montego Bay villa

3 bedrooms • 5 bathrooms • sleeps 6

1 review

from £283 / night

£1,789 - £2,250 / week

1 / 36

Holiday villa in Ocho Rios

Ocho Rios villa

3 bedrooms • 3 bathrooms • sleeps 6

from £151 / night

£1,053 / week

1 / 19

Holiday guest house in Falmouth

Falmouth guest house

2 bedrooms • 2 bathrooms • sleeps 4

5 reviews

from £46 / night

£305 - £465 / week

1 / 26

Portmore holiday home rental

Portmore house

3 bedrooms • 2 bathrooms • sleeps 6

from £142 / night

£753 / week

1 / 15

Apartment rental in Kingston

Kingston apartment

1 bedroom • 1 bathroom • sleeps 2

from £46 / night

£321 / week

1 / 13

Apartment rental in Ocho Rios with shared pool

Ocho Rios apartment

1 bedroom • 1 bathroom • sleeps 4

1 review

from £83 / night

£577 / week

1 / 26

Ocho Rios holiday condo rental

Ocho Rios condo

2 bedrooms • 2 bathrooms • sleeps 4

from £64 / night

£421 / week

1 / 7

Holiday apartment in Kingston

Kingston apartment

1 bedroom • 1 bathroom • sleeps 2

from £31 / night

£212 / week

1 / 9

Holiday villa in Negril

Negril villa

11 bedrooms • 13 bathrooms • sleeps 24

from £189 / night

£1,318 / week

1 / 22

Home rental in Discovery Bay

Discovery Bay house

3 bedrooms • 2 bathrooms • sleeps 5

from £72 / night

£502 / week

1 / 15

Jamaica holiday home rental

St James, Montego Bay house

2 bedrooms • 1 bathroom • sleeps 3

from £76 / night

£527 / week

1 / 4

Villa rental in Jamaica with swimming pool, golf nearby

Montego Bay villa

4 bedrooms • 4 bathrooms • sleeps 8

2 reviews

from £691 / night

£4,836 - £9,925 / week

1 / 29

Holiday studio letting

Ocho Rios studio

Studio • 2 bathrooms • sleeps 2

from £94 / night

£518 / week

1 / 12

Holiday guest house in Kingston

Kingston guest house

3 bedrooms • 2 bathrooms • sleeps 8

1 review

from £201 / night

£1,203 / week

1 / 12

Holiday apartment rental

Kingston apartment

1 bedroom • 1 bathroom • sleeps 3

“Cozy, Clean and Secure” I had a lovely stay - the apartment was clean, cozy and well-equipped. The air conditioning worked beautifully, and there were lots of cable channels. I particularly enjoyed the lovely little garden - it was the perfect spot to enjoy a cup of coffee or a glass of wine. Security was very tight, so I always felt safe. There was a minor hiccup with the wifi, but Bancroft worked very hard to resolve it and once that was sorted out, there were no other issues. I would definitely stay here again.

31 reviews

from £70 / night

£356 - £472 / week

1 / 35

Villa rental in Oracabessa with swimming pool

Oracabessa villa

4 bedrooms • 5 bathrooms • sleeps 6

9 reviews

from £292 / night

£2,040 / week

1 / 35

Holiday villa in Ocho Rios

Ocho Rios villa

2 bedrooms • 2 bathrooms • sleeps 4

“The best Ochi has to offer...” My wife and I travelled to Ocho Rios from Washington DC for a 10 day stay at Eden Sands. The Villa met and exceeded our expectations. From the delicious meals prepared by Barbara to the pristine beach right at your doorstep, if you want to stay as close to "the heart of Ochi" as you can while maintaining the comfort and relaxed atmosphere that any ideal Caribbean vacation requires this is the place for you! I highly doubt you'll ever find a need to leave the Villa (everything is provided for you) but if you should, dinning, nightlife, restaurants, and tourist attractions-including Dunn's River Falls and Mystic Mountain-are a short walk or taxi ride away. The Villa itself is perfect for a couples get away or a small nuclear family. My wife and I brought the in-laws, and they too enjoyed their stay immensely. In fact, other than his morning walk my father in-law did not leave the Villa once on our 10 day vacation. The food is also worth mentioning. As the spouse of a Jamaican national I'm no stranger to ackee and saltish, escovitch fish, curry goat, green banana, plantains, stew chicken, or the Jamaican treasure that is jerk pork. What you'll have at the Villa is as spectacular as you can get on the island, all that's required is a timely and polite request to your wonderful host Barbara and before long you and those that you choose to share this treasure of a rental property with will be dining on the scenic Caribbean sea. If you're looking for an authentic Caribbean getaway, this is the place for you!

40 reviews

from £412 / night

£2,880 / week

1 / 19

Holiday home in Manchioneal

Manchioneal house

4 bedrooms • 7 bathrooms • sleeps 10

from £207 / night

£1,448 / week

1 / 49

Kingston holiday apartment rental

Kingston apartment

1 bedroom • 1 bathroom • sleeps 2

2 reviews

from £66 / night

£462 / week

1 / 19

St. Ann's Bay holiday bungalow rental

St. Ann's Bay bungalow

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from £96 / night

£670 / week

1 / 16

Montego Bay holiday b&b rental

Montego Bay b&b

4 bedrooms • 4 bathrooms • sleeps 16

3 reviews

from £29 / night

£170 - £2,712 / week

1 / 34

Holiday guest house in Kingston

Kingston guest house

1 bedroom • 1 bathroom • sleeps 1

from £29 / night

£198 / week

1 / 12

Holiday home in Kingston

Kingston house

3 bedrooms • 4 bathrooms • sleeps 8

5 reviews

from £107 / night

£710 / week

1 / 29

Holiday apartment with golf nearby in Kingston

Kingston apartment

1 bedroom • 1 bathroom • sleeps 2

4 reviews

from £57 / night

£336 / week

1 / 4

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