50 Best Jamaica Estates on Holiday Lettings - Villas

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Saint James Parish
740 properties
Saint Ann Parish
664 properties
Kingston Parish
329 properties
Westmoreland Parish
201 properties
Trelawny Parish
166 properties
Saint Mary Parish
106 properties
Portland Parish
79 properties
Saint Catherine Parish
56 properties
Hanover Parish
47 properties
Saint Elizabeth Parish
39 properties
Manchester Parish
20 properties
Saint Andrew Parish
17 properties
Cabins Blue Mountains National Park
7 properties

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2,471 Vacation rentals

31

Vacation villa in Montego Bay

Saint James Parish / Montego Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Private garden
Pleasant View is a unique and immaculate air conditioned 3 bedroom villa luxuriously furnished with modern furnishings. Including outdoor bar, barbecue, large pool & other amenities. Seven miles west of Sangsters International Airport is Pleasant View, rapturo …see more

from $325 / night

$2210 / week

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from $325 / night

(1) Excellent 

29

Villa rental in Port Antonio

Port Antonio / Williamsfield

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Two elegant 1-bedrooms studio apartments, complete with bathroom, living room and kitchen—offer hosting to a maximum of 6 persons. Several outdoor terraces invite you to dine, unwind and relax while savoring idyllic tropical views. Immerse yourself, for nature's thera …see more

from $350 / night

$2000 / week

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from $350 / night

(8) Very Good 

23

Ocho Rios Vacation condo rental

Saint Ann Parish / Ocho Rios

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ask about 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's ba …see more

from $76 / night

$519 - $715 / week

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from $76 / night

13

Vacation home with shared pool in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 13 mi
  • Swimming pool
  • Child friendly
Island Vibz is located in close proximity to Ocho Rios Center, Dunn's River Falls, Dolphin Cove, Chukka Cove, Blue Hole, Konoko Falls, Marguaritaville, Duty Free Shops and many more local attractions....... This is the ideal vacation home for couples, solo adventurers, …see more

from $120 / night

$800 / week

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from $120 / night

(10) Excellent 

Certificate of Excellence

49

Ocho Rios Vacation 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 mi
  • Swimming pool
This refreshingly bright self-contained apartment is everything you might need to relax after a wonderful day at the beach. Located in the heart of Ocho Rios and strategically positioned for you to enjoy the ideal beachfront location. The area is teeming with mouthwate …see more

Certificate of Excellence

from $98 / night

$683 - $819 / week

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from $98 / night

10

Negril Beach Vacation 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 $100 / night

$700 - $1155 / week

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from $100 / night

13

Vacation 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 of lus …see more

from $68 / night

$765 / week

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from $68 / 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
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 $145 / night

$1015 / week

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from $145 / night

(3) Very Good 

11

Vacation villa in Runaway Bay

Saint Ann Parish / Runaway Bay

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Topaz Villa is situated in the quiet residential area of Cardiff Hall in Runaway Bay, St Ann's. The Villa boasts a large private swimming pool overlooking the golf club. The bedrooms are large and airy with ensuite and fans. There is a large lounge/diner for inside din …see more

from $195 / night

$1365 / week

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from $195 / night

(31) Very Good 

19

Vacation 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
This accommodation is a fully air-conditioned two bedroom apartment situated on the 3rd floor, you may rent this apartment as a one, or two bedroom see table rates. FREE INTERNET ACCESS The Apartment is tastefully furnished to a high standard, within the …see more

from $104 / night

$729 / week

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from $104 / night

(11) Very Good 

Certificate of Excellence

42

Runaway Bay Vacation apartment rental

Saint Ann Parish / Runaway Bay

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Cozy Tropical Paradise Vacation Apt! Spend the summer vacation in paradise, or escape the cold winter at Dreamy Haven, where it is sunny all year round, and sunbathing on white sand beaches sipping margaritas in the middle of winter is the norm. Experience home away fro …see more

Certificate of Excellence

from $70 / night

$490 / week

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from $70 / night

(14) Excellent 

27

Vacation home in Port Antonio

Port Antonio / Blue Lagoon, Port Antonio

4 9 1 night min

  • 4 bedrooms
  • Sleeps 9
  • 1 night min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
Mr Barrys is nestled nicely on a hill in the heart of Fairy HIll, Boston. We welcome visitors from around the world to stay with us and to feel at home here. Mr Barry's White House is in a quiet part of the Island and the locals are very warm and welcoming, there are …see more

from $200 / night

$1050 - $1200 / week

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from $200 / night

(10) Excellent 

Certificate of Excellence

25

Vacation 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 mi
  • Swimming pool
Tamarind Apartment is one of three lovely studios sharing the grounds and swimming pool with Pimento and Cinnamon apartments together with Almond Tree Villa. Only 10 mins from Ocho Rios centre and close to some beautiful beaches. Tamarind is on the ground floor below P …see more

Certificate of Excellence

from $49 / night

$312 - $390 / week

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from $49 / 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 mi
  • 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 are …see more

from $65 / night

$400 - $505 / week

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from $65 / night

(2) Good 

17

Portmore Vacation home rental

Saint Catherine Parish / Portmore

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This listing is a private, spacious, beautiful one bedroom within a two bedroom house. It is located in the sunshine community of Portmore, which is just a stone throw away from Kingston. NB. 2 or 3 bedroom is also available for rent, just ask. Between both houses I …see more

from $39 / night

$260 - $579 / week

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from $39 / night

7

Home rental in Old Harbour

Saint Catherine Parish / Old Harbour

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
2 Bedrooms, 1 Bathroom, Sleeps 4 This Beautiful Two Bedroom House Is Nestled In The Foothills Of New Harbour, St. Catherine. The House Is Located 25 Minutes from Kingston,45 minutes from Norman Manley Airport, 20 mins to Hellshire Beach, 25 mins to Caymanas Race Track …see more

from $52 / night

$338 - $475 / week

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from $52 / night

(4) Very Good 

Certificate of Excellence

20

Vacation apartment in Ocho Rios

Saint Ann Parish / Ocho Rios

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Child friendly
  • Private garden
Imagine a villa which has fabulous views, in a quiet location, with a spacious indoor Jacuzzi. This is a superb 3 bedroom holiday villa, in a quiet location yet minutes away from the fun and activities which the Ocho Rios scene can offer, such as Reggae Beach, Jet Ski r …see more

Certificate of Excellence

from $112 / night

$676 / week

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from $112 / night

13

Apartment rental in Old Harbour

Saint Catherine Parish / Old Harbour

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
Whole top floor home with one bedroom but can sleep 4; open plan kitchen, lounge, and dinging. Access to three balconies - two private and private pool with sheltered, sunny and shaded areas to relax. Rural location but easy access to old harbour with numerous bars, res …see more

from $38 / night

$260 / week

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from $38 / night

(1) Excellent 

29

Mammee Bay Vacation apartment rental

Saint Ann Parish / Mammee Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Beautiful North Coast Jamaican villa with private swimming pool, BBQ pit also spa retreat.   Only 5 minutes walk away from the most fabulous beach. This is in my opinion. the best location on the island Location, quality and the price for what you receiving for your …see more

from $104 / night

$650 / week

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from $104 / night

17

Westmoreland Parish Vacation guest house rental

Jamaica / Westmoreland Parish

4 16 1 night min

  • 4 bedrooms
  • Sleeps 16
  • 1 night min
  • Suitable for children age 5+
  • Car not necessary
Blue Paradise Farms is an Embryonic Permaculture Resort (eco-farm) set in 18.5 acres of lush Jamaican countryside, yet just 10 minutes away from Savanna-la-Mar, the parish capital and close to the main road from Savanna-la-Mar to Montego Bay. The accent here is on sust …see more

from $36 / night

$246 / week

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from $36 / night

(8) Excellent 

36

Vacation townhouse rental

Westmoreland Parish / Negril

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
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 $199 / night

$1750 - $3571 / week

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from $199 / night

32

Vacation apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • 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. The accommodations at Mystic Ridge feature large private balcony with views o …see more

from $130 / night

$767 / week

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from $130 / night

(2) Very Good 

35

Vacation 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 mi
  • 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 $104 / night

$507 - $729 / week

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from $104 / night

(1)  

9

Duncans Vacation cottage rental

Trelawny Parish / Duncans

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This is a 4 bedroom-bedroom fully Furnished house offering spacious living for 10. Children are welcome.Each bedroom has a large double bed and own bathroom.with the master bedroom features a Jacuzzi tub and shower.Some of the bedrooms are air condition with all …see more

from $150 / night

$900 / week

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from $150 / night

(1)  

26

Vacation 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
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 $60 / night

$400 / week

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from $60 / night

18

Long Bay Vacation home rental

Portland Parish / Long Bay

3 4 2 nights min

  • 3 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Private garden
OCEAN GARDEN HOUSE newly built house, located in a quiet, green and fresh area, consisting of fruit trees 100 meters from the beach. The rooms are protected by mosquito nets. The house consists of: 1 bedroom with bathroom and shower. 1 large bedroom with private bathroo …see more

from $100 / night

$700 / week

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from $100 / night

(4) Excellent 

Certificate of Excellence

32

Vacation studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Car not necessary
Cinnamon Apartment is one of three lovely studios sharing the grounds and swimming pool with Tamarind and Pimento apartments together with Almond Tree Villa. Cinnamon is built at the rear of the villa and looks out over the swimming pool terrace. The apartment is design …see more

Certificate of Excellence

from $49 / night

$312 - $390 / week

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from $49 / night

(3) Excellent 

56

Vacation apartment with golf nearby in Kingston

Kingston Parish / Kingston

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
  • Air conditioning
Lovely upscale spacious 2 bedroom apartment. This apartment is fully furnished and ready for holiday rental. Both rooms are fully air condition. Close proximity to spots such as Devon House, Halfway Tree, New Kingston and Sovereign Centre. It also have all the amenitie …see more

from $100 / night

$700 / week

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from $100 / night

(10) Excellent 

Certificate of Excellence

26

Vacation villa with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • 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

Certificate of Excellence

from $121 / night

$847 / week

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from $121 / night

(2) Good 

21

Vacation villa in Ironshore

Montego Bay / Ironshore

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Chateau Gloria Luxury Villa, your home away from home. Looking for place to relax? To enjoy the Jamaican spirit? Then this villa is perfect for you. The property offers its guests a private outdoor pool with bar, ocean view and is surrounded by a tropical g …see more

from $729 / night

$5096 - $6664 / week

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from $729 / night

38

Vacation home in Mandeville

Manchester Parish / Mandeville

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Nearest beach 24 mi
  • Child friendly
  • Private garden
A rustic space for you to unwind & rejuvenate in total tranquility & privacy. To quiet your mind, open your heart, and allow your body temple to return to a more relaxed state. Reconnect with the natural rhythms of nature and allow yourself this space to transform, a …see more

from $33 / night

$156 / week

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from $33 / night

(2) Excellent 

24

Villa rental in Jamaica with swimming pool, golf nearby

Saint James Parish / Montego Bay

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Sunset on the Beach, a charming 5 bedroom(beach house + cottage) private beach front villa located at the exclusively renowned Tryall Club in Montego Bay. Sunset on the Beach underwent a significant upgrade during the summer of 2016 (reopening in November 20 …see more

from $1949 / night

$13641 - $28000 / week

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from $1949 / night

(6) Very Good 

27

Negril Vacation 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 $729 / night

$5097 / week

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from $729 / night

17

Vacation 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 $100 / night

$700 - $1155 / week

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from $100 / night

4

Jamaica Vacation home rental

Montego Bay / St James, Montego Bay

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
We are a family living close to the airport and a big shopping plaza (a type of mall). We will treat you as another member of our family. We know it's nice to have a family when you're traveling and we want to treat our guest as such. We do offer picked up services for …see more

from $300 / night

$2020 / week

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from $300 / night

(18) Very Good 

Certificate of Excellence

25

Vacation villa with swimming pool in Ocho Rios

Saint Ann Parish / Ocho Rios

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
If you are looking for high standard, self-catering accommodation in Jamaica at a budget price you have just found the perfect holiday retreat. We offer everything you might possibly need for that perfect Jamaican vacation and please just compare our prices to what else …see more

Certificate of Excellence

from $104 / night

$650 - $1165 / week

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from $104 / night

(2) Excellent 

22

Vacation b&b in Jamaica

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 $195 / night

$1229 / week

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from $195 / night

(2) Excellent 

18

Duncans Vacation villa rental

Trelawny Parish / Duncans

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Location: The Yellow Canary Villa is a few steps to white sandy beach and is located half way between Montego Bay and Ochio Rios, off the north coast. The villa comes with our gourmet cook/housekeeper Joan and Sandra, Curtis gardener and Johnny our experienced driver. …see more

from $150 / night

$1000 - $1100 / week

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from $150 / 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
An awesome view of the beautiful Caribbean Sea from sitting on the porch in addition to all the comfort of a tastefully decorated home at a lower cost than most hotels in Ocho Rios, Jamaica. Available for your comfort is a master bedroom that has a king size bed with …see more

from $145 / night

$950 / week

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from $145 / night

(15) Very Good 

16

Vacation condo with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
A romantic peaceful setting but only ten minutes walk away from shops, restaurants and tourist attractions. Beautiful self catering condo, with stunning sea views overlooking the bay of Ocho Rios. Set in 14 acres of scenic landscaped gardens. This property is suitable f …see more

from $59 / night

$390 / week

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from $59 / night

With its own unique historical mix, Jamaica is a unique experience from the beaches of Negril to bustling Montego Bay, the people are warm and friendly and Jamaican music is famous the world over. With both the rich mixture of Kingston and idyllic resorts such Runaway Bay, Port Antonio and Discovery Bay, Jamaica has something for everyone.
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