Watersports holiday villas and apartments Jamaica | Holiday Lettings

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382 Holiday homes

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Travellers going to Jamaica are booking March dates now. Secure your holiday home today and have the perfect trip.

26

Holiday guest house in Long Bay

Portland Parish / Long Bay

5 8 2 nights min

  • 5 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Fall asleep to the lullaby of the ocean. Go for an adventure or just lounge or relax. One minute away from a stretch of white sand beach. Dine on delicious locally grown, organic foods. Near to all major attractions such as Blue Lagoon, Reach Falls and rafting on the R  …see more

from £50 / night

£328 / week

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from £50 / night

(6) Very Good 

21

Villa rental in Negril Beach with shared pool

Negril / Negril Beach

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
******** Our $450. per week special ends December 31, 2016 ********** Located on Norman Manley Blvd, Negril hip strip, directly across the street from Negril's famous 7 miles white sand beach. Access to the beach right across the street just a few steps away. We  …see more

from £54 / night

£328 - £632 / week

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from £54 / night

(31) Very Good 

77

Holiday villa with swimming pool, golf nearby in Ocho Rios

Saint Ann Parish / Ocho Rios

3 10 1 night min

  • 3 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“Had a wonderful time in Ocho Rios. Had a great stay at the condo, quiet and comfortable” The Property is very well maintained clean and tidy and the grounds are beautiful! Very classy in and out and very modernised. The pool was always clean and we  …see more

from £150 / night

£900 / week

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from £150 / night

(6) Very Good 

27

Negril holiday villa rental

Westmoreland Parish / Negril

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to the Villa 3, your Jamaican vacation beach home. Just steps from the sea, Villa 3 sleeps and entertains groups of 2 to 10 comfortably.The villa is located in the gated Little Bay Country Club: an exquisite, brand new, beachfront community in Negril. Vi  …see more

from £560 / night

£3920 / week

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from £560 / night

(3) Average 

18

Holiday condo with shared pool in Negril

Westmoreland Parish / Negril

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Negril' absolute beachfront studios, Carib Beach Apartments, for less than the cost of a hotel room, offer swimming-pool, Jacuzzi, choice of beach styles (one is clothing optional), on to uninterrupted beach over 4 miles with atmospheric bars, carvings, cafes etc.&  …see more

from £82 / night

£410 - £738 / week

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from £82 / night

(5) Very Good 

10

St James, Montego Bay holiday condo rental

Montego Bay / St James, Montego Bay

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.6 km
  • Swimming pool
condo, apartment in montego bay , montego bay condo, one bedroom condo in jamaica<br />Guests have full access to the Palmyra Resort grounds with onsite fitness facility  …see more

from £115 / night

£804 / week

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from £115 / night

(5) Excellent 

26

Holiday villa with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Situated on Jamaica's north coast, in a gated community with twenty four hour security. Nearby attractions include: Dunn's River Falls, Dolphin Cove and Mystic Mountain. Onsite pool, gym, tennis courts, children's play area and park. Daily housekeeper  …see more

from £93 / night

£651 / week

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from £93 / night

(25) Very Good 

19

Holiday apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Ideal location!” A friend of mine goes to Jamaica every year and since I hadn’t visited for quite some time, so I decided why not. From the initial communication with Jacqueline I was put at ease. Communication was always prompt and pleasant and  …see more

from £80 / night

£560 / week

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from £80 / night

(1) Excellent 

41

Ocho Rios holiday apartment let

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
Fishermans point resort is a one Bedroom beach apartment (living room, bedroom, kitchen, bath room), beach 3 minutes walk, with ocean view, located in Ocho Rios Turtle Street Mahogany Beach. The spacious apartments sleeps 4, Cable TV. The living and dining area a  …see more

from £70 / night

£350 - £590 / week

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from £70 / night

(2) Excellent 

33

Holiday townhouse rental

Westmoreland Parish / Negril

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This newly built two bedroom, two and a half bathroom townhouse, located on the cliffs, overlooking the ocean, is the perfect home away from home for your holiday, or stay in Negril, Jamaica. It easily sleeps 6 guests. The king bedroom can be separated into 2 twin bed  …see more

from £205 / night

£1435 - £2582 / week

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from £205 / night

(3) Excellent 

24

Holiday studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 km
  • Car not necessary
“A warm welcome in a well equiped studio apartment for a lovely stay.” We stayed for several weeks at Cinnamon studio this summer and really enjoyed our stay. Renée and Nigel who oversee the Almond Tree Villa house and apartments were very kind and hel  …see more

from £35 / night

£230 - £300 / week

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from £35 / night

(1) Excellent 

26

Ocho Rios holiday studio rental

Saint Ann Parish / Ocho Rios

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 1 km
  • Swimming pool
  • Car not necessary
Pimento is a delightful spacious studio, one of three apartments overlooking the pool at Almond Tree Villa. Quiet upscale area, one of the nicest locations in Ocho Rios. Only 3 miles from the center of town and close to postcard perfect beaches. Lovely swimming pool and  …see more

from £40 / night

£250 - £315 / week

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from £40 / night

(1) Excellent 

23

Holiday villa with swimming pool, golf nearby in Runaway Bay

Saint Ann Parish / Runaway Bay

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Whistling villa is one of the most affordable private villas with pool in Runaway Bay. Free access to public beach and shared private private beach for villa guests is just minutes away.Whistling villa is adjacentto Runaway bay's 18-hole, pga-quality golf course.  …see more

from £234 / night

£1636 / week

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from £234 / night

(6) Very Good 

34

Ocho Rios holiday condo rental

Saint Ann Parish / Ocho Rios

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Most Relaxing Holiday Ever” My son & I had never been to Jamaica before... traveled with friends that were born in Jamaica. People in Jamaica are the most genuine people on earth. They are so kind, helpful and always happy. I definitely will be goi  …see more

from £90 / night

£600 / week

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from £90 / night

22

Holiday guest house in Falmouth

Trelawny Parish / Falmouth

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
This is Charmaine's 2 Bedroom guest house. It is a spacious and beautiful private destination that is situated in the middle of Montego Bay and Ocho Rios. The house is newly built in 2015 and is a gated community. The guest house is close to all tourist attraction  …see more

from £65 / night

£455 / week

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from £65 / night

(8) Very Good 

23

Ocho Rios holiday condo let

Saint Ann Parish / Ocho Rios

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Ask owner if suitable for children
Carib Condominiums are located on a private beach on Main street, Ocho Rios.This privately owned and managed apartment is located on the top floor of this 2 storey apartment building. Here you can see magnificant views of the Caribbean Sea from your condo'  …see more

from £58 / night

£399 - £550 / week

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from £58 / night

13

Holiday studio in Negril Beach

Negril / Negril Beach

Studio 2 1 night min

  • Studio
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
The studio is located inside the beach complex The Point right on Jamaica's 7 mile beach in Negril. The suite as a beautiful ocean-view from inside the unit and balcony. There is a kitchenette with full appliances, and Queen size bed.. Located on over 14 acres o  …see more

from £56 / night

£626 / week

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from £56 / night

(8) Very Good 

37

Runaway Bay holiday apartment rental

Saint Ann Parish / Runaway Bay

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Perfect Vacation Apt!!!” This vacation apt is the best that I have stayed. It was ideally situated near all attractions, stores, day and night activities, beaches, restaurants. I could literally walk to the nearest beach and restaurant. the apt was co  …see more

from £58 / night

£402 / week

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from £58 / night

(10) Very Good 

25

Holiday studio with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Amazing” The apartment was wonderful!!! My partner and I felt comfortable inside the apartment which was fully equipped. It was definetly worth our time. Staff are also helpful and a delight to be around. You will not be disappointed upon your stay at  …see more

from £37 / night

£240 - £300 / week

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from £37 / night

(3) Excellent 

15

Holiday apartment rental

Montego Bay / St James, Montego Bay

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Child friendly
“Absolutely amazing, perfect stay no trouble no regrets” My stay at westgate hills was truly a home away from home, on arrival at the property I was greeted by the caretaker wilbert one of the nicest people you will ever meet the house is beautiful a  …see more

from £50 / night

£270 - £405 / week

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from £50 / night

(1) Excellent 

62

Villa rental in St. Ann's Bay with shared pool

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Gorgeous and affordable 3 bedroom Villa Ocho Rios St Ann Jamaica, perfect holiday getaway.  …see more

from £119 / night

£779 / week

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from £119 / night

10

Villa rental in Long Bay

Portland Parish / Long Bay

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
A vacation home away from home with probably the best view in Long bay. With just steps from the beach and a short drive to Port Antonio or other nearby attractions you can enjoy a fun relaxing island vacation. There are 4 spacey bedrooms available for rent (or entire h  …see more

from £29 / night

£181 - £402 / week

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from £29 / night

(2) Very Good 

29

Holiday apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
The Resort is situated on 19 acres of lush landscaped gardens with 90 story residences surrounding a freshwater swimming pool, swim-up bar, whirlpool and bar. There are also two tennis courts and a Spa. Beach 7 minutes walk from apartment. We also have rentals at S  …see more

from £75 / night

£350 - £590 / week

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from £75 / night

26

Holiday villa accommodation

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Welcome to Fortlands Point on the Beach, one of the world's most exquisite and luxurious 7 bedroom beachfront mansions located on a private promontory with its own private beach, swimming pool extensive gardens. Set amongst stunning landscaped gardens with tropical  …see more

from £2108 / night

£14755 - £25410 / week

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from £2108 / night

20

Holiday villa with swimming pool in Mammee Bay

Saint Ann Parish / Mammee Bay

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
Fully staffed villa, set in private tropical gardens of Mammee Bay Estate. You choose, wonderful pool or Caribbean sea!. Lots of outdoor spots for relaxing. Great sea views from the spacious roof terrace with lounging area and wet bar. 5mins walk to the private beach. P  …see more

from £350 / night

£2500 / week

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from £350 / night

(1) Excellent 

15

Holiday studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Ocho Rios, Jamaica  …see more

from £73 / night

£492 / week

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from £73 / night

(5) Average 

32

Ski apartment to rent in Ocho Rios

Saint Ann Parish / Ocho Rios

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ski
FREE WIFIBeautiful beachfront apartment, villa, condo, vacation rental Ocho rios, Jamaica, cheap, affordable sea, sun, sunshine, fun, family, getaway<br />FREE WIFI, NETFLIX  …see more

from £73 / night

£511 / week

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from £73 / night

(3) Very Good 

35

Holiday apartment rental

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
Fishermans point resort is a one Bedroom beach apartment (living room, bedroom, kitchen, bath room), beach 3 minutes walk, with ocean view, located in Ocho Rios Turtle Street Mahogany Beach. The spacious apartments sleeps 4, Cable TV. The living and dining area a  …see more

from £70 / night

£350 - £520 / week

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from £70 / night

29

Holiday condo rental

Westmoreland Parish / Negril

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
This wonderful one bedroom Queen suite as a glorious sea view's and is the perfect rental for a couple or small family. Located on the second floor the suite as a galley style kitchen, full appliances with utensils and coffee maker. Bathroom with tub, living room  …see more

from £91 / night

£628 - £959 / week

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from £91 / night

(6) Excellent 

49

Ocho Rios holiday apartment rental

Saint Ann Parish / Ocho Rios

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Ms” Beautiful gem in a great location, close to shops, restaurants and entertainment. Superbly clean and modern. The listing is exactly as the description. Suzzane and Ms. Theresa are a great team. They made every effort to make my stay a pleasant and  …see more

from £75 / night

£525 - £630 / week

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from £75 / night

28

Studio rental in Negril with shared pool

Westmoreland Parish / Negril

Studio 3 1 night min

  • Studio
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Breath taking sea views and romantic sunsets are just part of what this Superior studio suite as to offer. Located on Negril's famous 7 mile suite, the sand and water is just a few steps away from your your feet. Enjoy the private beaches or venture on to the publi  …see more

from £74 / night

£480 - £726 / week

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from £74 / night

(10) Excellent 

42

Runaway Bay holiday bungalow rental

Saint Ann Parish / Runaway Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 2 km
  • Swimming pool
  • Child friendly
Contemporary stylish beach villa located along Jamaica's picturesque north coast Runaway Bay :) Villa is located in a secure upmarket gated community called Richmond. The community is quiet and safe with 24 hour security. There is also a supermarket located on th  …see more

from £82 / night

£574 / week

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from £82 / night

(5) Very Good 

34

Villa rental in St. Ann's Bay with golf nearby

Saint Ann Parish / St. Ann's Bay

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
“Perfect relaxing and accommodation villa.” We spent 3 nights with family and friends at the villa. We enjoyed our stay as every where was convenient to us by car. Villa was clean and Mr Onair was only a phone call if we needed anything. Thanks for a l  …see more

from £119 / night

£832 / week

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from £119 / night

45

Holiday villa in Port Antonio

Portland Parish / Port Antonio

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
Deja Vu villa belongs to the list of villas at the Blue Lagoon that have been the most photographed houses in the whole of the Caribbean.  …see more

from £1230 / night

£6558 / week

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from £1230 / night

37

Holiday apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
This rental is in the fruited grounds off Villa Patiently Waiting, in the presitgious Mamme Bay Estate with 24 hours security. Located in Villa Patiently Waiting an established holiday rental This property consists of one large room with 2 double beds, TV, sound syste  …see more

from £54 / night

£328 - £386 / week

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from £54 / night

4

Jamaica holiday home rental

Montego Bay / St James, Montego Bay

2 3 2 nights min

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Stay with the locals instead of an hotel. Located near to Chukka Adventure Tours, Pier 1, Margaritaville, Sumfest, etc.  …see more

from £246 / night

£1656 / week

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from £246 / night

10

Negril Beach holiday condo rental

Negril / Negril Beach

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Beautifully decorated one bedroom ocean view suite on the beach. Just a few steps away from the water, with the sound of the waves and the cool breeze flowing in its a great relaxation spot to be lazy and unwind. The suite sleeps up to four people comfortably, with a Qu  …see more

from £85 / night

£591 - £947 / week

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from £85 / night

(1) Excellent 

25

Holiday villa in Ocho Rios

Saint Ann Parish / Ocho Rios

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
BeachfrontSnorkelingDeep Sea FishingPrivate Beach  …see more

from £290 / night

£1900 / week

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from £290 / night

17

Holiday condo in Negril Beach

Negril / Negril Beach

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
This beautifully decorated one bedroom suite sleeps a maximum of 4 people. The suite as a Kind bed in the main bedroom and two twin size sofa beds in the living room for extra sleeping space. There is relaxing bathtub with shower, a galley style kitchen complete with fu  …see more

from £90 / night

£603 - £947 / week

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from £90 / night

(4) Excellent 

20

Holiday villa with swimming pool, golf nearby in Runaway Bay

Saint Ann Parish / Runaway Bay

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Great alternative to All Inclusives” Roger and the Pegasus staff are wonderful to deal with. Our stay was an awesome way to really be in Jamaica. Taxis and busses easy to get around into Ochos and Montego Bay and very reasonable. Lot of fun going i  …see more

from £160 / night

£880 / week

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from £160 / night

Top Destination reviews

Beautiful Waterfront Apt across from Beach Club
Beautiful place - couldn't ask for any better

Central location, beautiful apartment and excellent views. The flat was very clean, quiet, secure and private. I enjoyed watching the cruise ships docking across the bay and also enjoyed using the beach at the nearby Sea Wind on the Bay (5 mins walk … see more
Garden Villa Ocho Rios St.Ann
Saying good bye is never easy

Our stay at Gradens Villa was wonderfull to say the least. Mr Barns was very accommodating as well as the house keeper that took care of all our needs. I love this place so much that we are booked for the first week of August. Clarke's family.. … see more
Island Treasure Villas
TRULY AN……Island Treasure Villla

Our stay at Island Treasure Villas was beyond what was expected! From the moment of booking to the end of our stay at this wonderful villa the professionalism of the owner and staff was truly top notch. We decided to stay based on the amazing pho … see more
JamRest Villas
Excellent holiday

Had a wonderful time in Jamaica. Really glad we stayed at Jamrest. It is as beautiful as the photos and we were thankful to have met Suzie; such a lovely person and excellent housekeeper, who maintains the house to a high standard. Suzie was so frien … see more
A Newly Renovated Oceanfront Studio in Negril with Breathtaking Views!!!!!!!!!!!
Point village negril

Beautiful setting fantastic apartment with lots of good food places to eat both Jamaican and European food within a short taxi drive. Apartment had everything you could need and located very close to the beach at point village for sborkling and swim … see more
Sunshine Reggae Villa
Great Resort Style Living

I saw many similar properties at Cool Shades/ Richmond advertised on online. I selected Sunshine Reggae Villa largely based on the reviews. On my arrival I was happy to find that even after reading the reviews, the property exceeded my expectations.. … see more