Cycling holiday villas and apartments Jamaica | Holiday Lettings

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Saint James Parish
828 properties
Saint Ann Parish
670 properties
Kingston Parish
320 properties
Westmoreland Parish
214 properties
Trelawny Parish
166 properties
Saint Mary Parish
107 properties
Portland Parish
65 properties
Hanover Parish
51 properties
Saint Catherine Parish
49 properties
Saint Elizabeth Parish
33 properties
Manchester Parish
22 properties
Saint Andrew Parish
17 properties
Blue Mountains National Park
7 properties
Jamaica holidays
2,603 properties
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90 Holiday homes

Filters applied: Cycling holidays (90)

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

28

Villa Rasta/ Panoramica Ocean view bungalows - Long Bay guest house sleeps 8

Portland Parish / Long Bay

5 8 2 nights min

  • 5 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
This is Rasta Villa Guest house with 4 bungalows to choose from, all ocean views Born an Bread in Portland and I still believe its one of the most beautiful place in the world. Lush greenery, peaceful ambiance , some of the friendliest people you will ever meet. Many  …see more

from £31 / night

£185 - £308 / week

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from £31 / night

(4) Excellent 

26

Serenity Villa - Ocho Rios villa sleeps 6

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 to assist with  …see more

from £100 / night

£700 / week

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from £100 / night

(8) Excellent 

16

Hill Top Villa - Treasure Beach villa sleeps 6

Saint Elizabeth Parish / Treasure Beach

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Modern spacious fully furnished 2 double bedrooms (sleeps up to six) villa to rent in the town of Junction, St Elizabeth, in Jamaica's Countryside on the South Coast of the Island. Light bright and airy. Located on a private hill with breath taking views all aro  …see more

from £47 / night

£329 - £665 / week

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from £47 / night

(4) Very Good 

34

Luxury Vacation Home with Free WIFI - St. Ann's Bay villa sleeps 8

Saint Ann Parish / St. Ann's Bay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
With the beauty of nature as its backdrop, Island Treasure Villas offer its guests a tranquil island escape that provides all the comfort of home with the flair and amenities of a luxury hotel. A stay at this luxurious 3 bed, 2 baths villa provide guests with access to  …see more

from £112 / night

£781 / week

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from £112 / night

21

Fortlands Point - 7 Bedrooms - Private Beach - Discovery Bay villa sleeps 14

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 £1978 / night

£13847 - £23847 / week

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from £1978 / night

(2) Excellent 

17

Calypso Shores on the Beach- 4 Bedrooms - Montego Bay villa sleeps 8

Saint James Parish / Montego Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Calypso Shores, a luxurious contemporary 4-bedroom beachfront villa located on its own private beach on a calm lagoon in Montego Bay in Jamaica. Calypso Shores, located in a stunning California-style residential neighbourhood named Lagoons, is possibly one of  …see more

from £658 / night

£4604 - £10385 / week

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from £658 / night

5

Elegant 2 bedroom - Portmore house sleeps 4

Saint Catherine Parish / Portmore

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Private garden
This is a beautiful, tastefully decorated house upstairs. This apartment was recently built. Pictures do not reflect the true beauty of this place. It has 3 b/room (2 bedrooms for rent), each room has its own bathroom. You have access to kitchen, living, dining and bal  …see more

from £42 / night

£275 - £305 / week

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from £42 / night

(5) Excellent 

21

Ocean Wave Villa Negril, $400 per week special - Negril Beach villa sleeps 3

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 starts April 1, 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 are lo  …see more

from £50 / night

£308 - £620 / week

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from £50 / night

(1) Good 

7

Carib Beach Apartment 2 - Negril apartment sleeps 3

Westmoreland Parish / Negril

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Just two beachfront apartments on Negril's famous 7-mile beach, in a secure, low-density condominium setting.Your spacious balcony looks out over the Caribbean Sea across a lawn with coconut trees, oleander and bougainvillaea flowers. Don't let the low price p  …see more

from £100 / night

£647 / week

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from £100 / night

(3) Excellent 

15

Melrose place Westgate Hills - St James - Montego Bay apartment sleeps 7

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
Apartment comprises 2 double bedrooms both with double beds and one bedroom has a single additional bed. Lounge/dinning room comprise sofa and a double sofa bed. TV with dinning table and chairs. Now also with WiFi. The kitchen is fully working with cooker, fridge and M  …see more

from £50 / night

£260 - £425 / week

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from £50 / night

(1) Very Good 

20

Ocho Rios Self Contained Studio Pool Wifi Security - Ocho Rios apartment sleeps 2

Saint Ann Parish / Ocho Rios

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Ask owner if suitable for children
HURRY RESERVE NOW BEFORE SOMEONE ELSE GETS YOUR REQUIRED DATES!.*Automatic discounted rates for reservations 7 nights and above.*Massive automatic discounts on monthly rates.Purpose built self-contained apartment (you are not sharing in any way), your own front door and  …see more

from £40 / night

£260 / week

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from £40 / night

24

Sunset on the Beach - 3 bedrooms - Montego Bay villa sleeps 6

Saint James Parish / Montego Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Sunset on the Beach, a charming 3 bedroom private beach front villa located at the exclusively renowned Tryall Club in Montego Bay. The stunning turquoise blue all-day view is topped off by a unique sunset sky and a spectacular nighttime view of the sparkling  …see more

from £1484 / night

£10385 - £21539 / week

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from £1484 / night

24

Villa Sunrise at Round Hill - 2 bedrooms - Montego Bay villa sleeps 4

Saint James Parish / Montego Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Villa Sunrise, a luxurious 2 bedroom private villa located in the exclusive world renowned Round Hill in the stunning Montego Bay area. Villa Sunrise was very recently renovated yet it has retained the original style of classy Round Hill. This pretty cottage  …see more

from £1334 / night

£9337 - £12229 / week

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from £1334 / night

24

Valencia Villa Jamaica - Ocho Rios villa sleeps 6

Saint Ann Parish / Ocho Rios

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
**Our rates do not include cost of transportation,food & beverages,Chef service,staff gratuities, use of outdoor Jacuzzi Hot Tub. ** Valencia is a family owned and operated private Luxury villa. We are located in the beautiful St Ann parish, in the gated community of M  …see more

from £275 / night

£1924 / week

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from £275 / night

(5) Excellent 

16

The Village Rose Hall - Rose Hall house sleeps 4

Montego Bay / Rose Hall

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Bright two bed room Villa located in Rose Hall Montego Bay. beach, bars, and restaurants, all within 10 minutes drive to the beach The Space Ocean view Condo' Great 2 bedroom Villa in Montego Bay, centrally located Rose Hall opposite the Hilton HotelSpend th  …see more

from £50 / night

£400 - £610 / week

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from £50 / night

5

Villa by the Sea - Little Bay villa sleeps 6

Westmoreland Parish / Little Bay

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
In addition to Sandys by the Sea we now offer another option for your holiday on the island of Jamaica!We have a brand new Villa!Coral stone showers, complete kitchen for your cooking needs and it's located just a three minute walk from here and the beach.Lovely, p  …see more

from £231 / night

£1616 / week

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from £231 / night

25

Eden Sands Beach - Ocho Rios villa sleeps 5

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
Eden Sands, Ocho Rios is a privately owned villa ideally located in the centre of town. Eden Sands boasts its own private white sand beach next to Neptune Vila. Eden Sands is perfect for week-long vacations, weekend getaways, writer's retreats, house-hunting visi  …see more

from £290 / night

£1900 / week

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from £290 / night

(2) Excellent 

22

Agapantha Cottage - Blue Mountains National Park b&b sleeps 6

Jamaica / Blue Mountains National Park

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Private garden
Agapantha Cottage is a quiet country retreat where you can get away for a relaxing weekend or longer to enjoy the serenity and pleasant climate of Mandeville. Located on the outskirts of the town centre we are also a great alternative to a hotel for the visitor doing b  …see more

from £58 / night

£324 / week

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from £58 / night

(13) Excellent 

21

Turtle Towers - Ocho Rios apartment sleeps 4

Saint Ann Parish / Ocho Rios

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
One bedroom with king size bed . Being on the ground floor it is verysafe for children who like to climb on the balcony. Also easy access for wheelchair users. Very quiet and peaceful at night.Fully equipped with air conditioning telephone, microwave, cooker, full siz  …see more

from £60 / night

£420 / week

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from £60 / night

15

Blue Mountain Villa, St Elizabeth - Blue Mountains National Park villa sleeps 12

Jamaica / Blue Mountains National Park

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Blue Mountain Villa is located in the heart of the St Elizabeth countryside and has breathtaking views overlooking the Carribean Ocean and the Blue Mountain Range as a spectacular backdrop. A luxurious destination retreat for families and friends, reunions, romantic get  …see more

from £314 / night

£2200 / week

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from £314 / night

(1) Very Good 

27

DOMINIQUE'S GETAWAY,ST. CATHERINE-JA- NEAR GO - Portmore apartment sleeps 5

Saint Catherine Parish / Portmore

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Car not necessary
  • Private garden
ARE YOU VISITNG JAMAICA FROM OVERSEAS? ATTENDING A CRICKET MATCH AT THE FAMOUS SABINA PARK? ON A BUDGET? ADVENTUROUS? INTO HISTORICAL RESEARCH? WANT SOMEPLACE OFF THE BEATEN PATH & AWAY FROM IT ALL? WANT TO ENJOY THE REAL JAMAICA? Don't waste your $$ mo  …see more

from £108 / night

£754 / week

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from £108 / night

13

Villa Barbary - Villa with a View! - Ocho Rios villa sleeps 10

Saint Ann Parish / Ocho Rios

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool
Set on 2.5 acres of private Jamaican hillside overlooking Ocho Rios, Barbary provides you with the seclusion of a private estate within just minutes drive of the sights and attractions of Ocho Rios and Jamaica's north shore.• 4 Bedrooms for 2+ people in each!•  …see more

from £354 / night

£2231 - £2539 / week

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from £354 / night

(1) Excellent 

35

Studio Apartment - Ocho Rios studio sleeps 4

Saint Ann Parish / Ocho Rios

Studio 4 1 night min

  • Studio
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
This property is located on one of the most prestigious locations in Jamaica Villa Patiently Waiting is set in one and half acres of landscaped gardens with lots of indigenous plants, flowers and fruit bearing tress. This beautiful Jamaican studio is in the prestigious  …see more

from £60 / night

£350 / week

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from £60 / night

(1) Good 

13

Hellshire Holiday Villas - Hellshire house sleeps 6

Portmore / Hellshire

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Holiday Villas Hellshire is located in the Secure Gated Community of Cavehill Estate, Hellshire, St Catherine, Portmore Jamaica. We offer holiday villas for the perfect holiday getaway. We are located just 5 minutes walk from the world famous Fisherman's Beach at  …see more

from £30 / night

£210 - £280 / week

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from £30 / night

7

Pearl Ocean Villa - Port Antonio guest house sleeps 6

Portland Parish / Port Antonio

6 6 2 nights min

  • 6 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
The villa consist of 6 double bedrooms and 1 twin bedroom room, 2 bedroom, self-catering apartment. From the dining room and living room areas you will immediately capture the lovely breath taking panoramic view of the ocean and steep lush and fruitful hills. The pr  …see more

from £50 / night

£385 / week

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from £50 / night

(1) Good 

17

JSH LETTINGS - Runaway Bay guest house sleeps 6

Saint Ann Parish / Runaway Bay

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Richmond Estate Is Located On A Northern Coastal Property near the Resort Town Of St Anns Bay. It Is nestled between Runaway Bay and Priory, With A Breathtaking View Of The Caribbean Sea. Richmond St. Ann is an easy 50-minute drive from the Sangster International Airpor  …see more

from £80 / night

£595 / week

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from £80 / night

(13) Excellent 

24

Saint James Parish / Montego Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

 …see more

from £138 / night

£964 / week

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from £138 / night

(1) Terrible 

12

Rafjam Kingston Hostel - Kingston guest house sleeps 8

Kingston Parish / Kingston

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Child friendly
"Rafjam Kingston Hostel" is the newest addition to the "Rafjam" family. Located in a neighborhood of quietude and privacy, this property is perfect for unwinding after a long flight. Rafjam aims to please. The tag line being; "service beyond e  …see more

from £175 / night

£1050 / week

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from £175 / night

(1) Very Good 

14

Westmoreland Parish / Negril

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £143 / night

£997 - £2262 / week

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from £143 / night

19

Saint Ann Parish / Ocho Rios

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool

 …see more

from £347 / night

£2231 - £2770 / week

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from £347 / night

43

Saint Thomas Parish / Morant Bay

20 42 1 night min

  • 20 bedrooms
  • Sleeps 42
  • 1 night min
  • Nearest beach 0.5 km
  • Child friendly
  • Car not necessary

 …see more

from £39 / night

£216 / week

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from £39 / night

(2) Very Good 

20

Montego Bay / St James, Montego Bay

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ski

 …see more

from £81 / night

£585 - £1662 / week

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from £81 / night

38

Treasure Beach / Parish of St. Elizabeth

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

 …see more

from £200 / night

£1231 / week

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from £200 / night

(5) Excellent 

38

Trelawny Parish / Falmouth

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 4 km
  • Child friendly
  • Air conditioning

 …see more

from £35 / night

£234 / week

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from £35 / night

(10) Excellent 

31

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 13 km
  • Swimming pool

 …see more

from £84 / night

£631 - £954 / week

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from £84 / night

12

Negril / Negril Beach

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from £193 / night

£1347 - £2289 / week

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from £193 / night

(3) Very Good 

43

Saint Ann Parish / Ocho Rios

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool

 …see more

from £104 / night

£693 / week

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from £104 / night

(1) Excellent 

20

Hanover Parish / Lucea

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £154 / night

£1077 / week

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from £154 / night

10

Negril / Negril Beach

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from £177 / night

£1239 - £2020 / week

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from £177 / night

11

Kingston Parish / Kingston

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Suitable for children age 5+

 …see more

from £93 / night

£593 / week

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from £93 / night

Top Destination reviews

Tamarind Studio Apartment - Pool, Wi-Fi, Ocho Rios
wish you was there with me

make shore you dont have a lot off running around to do and you have lots off refreshment and snacks to enjoy whilst you relax in the pool. Bring your laptop with you it saved me a lot off trouble contacting people around the world it also helps yo … see more
Island Treasure Villas
TRULY ANIsland 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
Tamarind Studio Apartment with Swimming Pool and minutes from Ocho Rios
wish you was there with me

make shore you dont have a lot off running around to do and you have lots off refreshment and snacks to enjoy whilst you relax in the pool. Bring your laptop with you it saved me a lot off trouble contacting people around the world it also helps yo … 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
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

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