50 Best Jamaica Estates on Holiday Lettings - Villas

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Saint Ann Parish
639 properties
Saint James Parish
610 properties
Kingston Parish
338 properties
Westmoreland Parish
189 properties
Trelawny Parish
169 properties
Saint Mary Parish
102 properties
Portland Parish
78 properties
Saint Catherine Parish
62 properties
Hanover Parish
48 properties
Saint Elizabeth Parish
40 properties
Manchester Parish
16 properties
Saint Andrew Parish
15 properties
Cabins Blue Mountains National Park
9 properties

Jamaica

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2,351 Vacation rentals

(5) Excellent 

37

Vacation apartment with shared pool in Port Royal

Kingston / Port Royal

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
My place is close to family-friendly activities, nightlife, public transport, the airport, and the beach. You’ll love my place because of the views, the location,, the people, the cosiness, the high ceilings. My place is good for couples, solo adventurers, business trav …see more

from $100 / night

$700 / week

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avg. 47 minutes

from $100 / 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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Responds fast!
avg. 2 hours 43 minutes

from $100 / night

30

Vacation home in Bull Bay

Saint Andrew Parish / Bull Bay

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
Beautiful home in Bull Bay, on the S/E coast of JA, 10 minutes from Kingston 10 miles East of Kingston. Minutes from beaches and town. Feel true culture. Large gated property, XXLarge bedrooms and bathrooms. High ceiling and huge windows for the most tropical breeze i …see more

from $30 / night

$211 / week

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from $30 / 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 - $506 / week

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from $65 / night

7

Villa accommodation in Buff Bay

Portland Parish / Buff Bay

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets
Windbreak villa is situated in the coastal parish of Portland, within the beautiful, popular housing scheme of Woodstock in the town of buff bay. Windbreak villa is the perfect setting for a family vacation or secluded, quit, romantic getaway. come visit us at windbreak …see more

from $200 / night

$1400 / week

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from $200 / 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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avg. 3 hours 13 minutes

from $100 / night

(3) Good 

18

Vacation condo with shared pool in Negril

Westmoreland Parish / Negril

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 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 oleander and bougainvillaea flowers. Don't let the low price put you off; this is a …see more

from $80 / night

$480 - $900 / week

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from $80 / night

(3) Excellent 

7

Vacation apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Beautiful newly decorated one bedroom Suite. This is your home away from home. You can walk easily to the town for restaurants and entertainment. But, you really have no need as there is restaurant and pool onsite. The beaches are a short drive or walk away and many …see more

from $92 / night

$590 / week

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from $92 / 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

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 $328 / night

$2227 / week

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avg. 2 hours 28 minutes

from $328 / 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 $40 / night

$262 - $583 / week

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from $40 / 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 $734 / night

$5136 / week

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from $734 / night

(10) 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 $200 / night

$1750 - $3570 / week

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avg. 2 hours 6 minutes

from $200 / 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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avg. 3 hours 4 minutes

from $120 / night

(9) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from $76 / night

$523 - $758 / week

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avg. 1 hour 51 minutes

from $76 / 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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Responds fast!
avg. 3 hours 26 minutes

from $200 / night

(4) Excellent 

12

Vacation villa with shared pool, golf nearby in Jamaica

Montego Bay / Rose Hall

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Surround yourself with timeless elegance. Mahogany House is surrounded by lush, green, tropical gardens and unbeatable breathtaking views. Features overly spacious bedrooms that open out to balcony, pool deck and living areas. Relax and soak up the sun by the pool with …see more

from $276 / night

$1926 / week

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avg. 1 hour 26 minutes

from $276 / night

(13) Excellent 

40

Runaway Bay Vacation bungalow rental

Saint Ann Parish / Runaway Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 2 mi
  • 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 the com …see more

from $125 / night

$875 / week

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avg. 2 hours 4 minutes

from $125 / night

(1) Excellent 

44

Ocho Rios Vacation 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 mi
  • 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 $92 / night

$511 - $826 / week

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from $92 / 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 $105 / night

$734 / week

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avg. 2 hours 52 minutes

from $105 / 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

(1) Very Good 

8

Vacation home in Boscobel

Saint Mary Parish / Boscobel

3 10 2 nights min

  • 3 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
  • Car not necessary
Modern Large cool onsuite rooms with a through lounge which includes a relaxing lounge dining room and modern fitted kitchen. you have a view of the sea from the front of house and lush green hills from the back. its 10 minutes from the famous James bond beach with man …see more

from $27 / night

$197 - $1009 / week

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from $27 / night

(3) Good 

36

Ocho Rios Vacation apartment rental

Saint Ann Parish / Ocho Rios

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Hotel Features. This 2bed Penthouse apartment in a resort, features a pool attached to a swim-up bar and an eight-person jetted tub. Beach 7 minutes away.One king bed, two-person jetted Jacuz tub, vanity sink in master bedroom located in loft with peaked wood ceili …see more

from $131 / night

$773 - $904 / week

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from $131 / 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

$315 - $393 / week

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avg. 2 hours 24 minutes

from $49 / 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 mi
  • 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 $40 / night

$280 - $490 / week

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from $40 / 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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avg. 3 hours 13 minutes

from $68 / night

(1) Very Good 

19

Vacation apartment rental

Saint Mary Parish / Tower Isle

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
The flat is in a 24 hour Gated community. It is a clean 1 Bed / 1 Dinning Room / Kitchen and Bathroom apartment and the use of a self catering kitchen. Rio Nuevo Battle Site, Spring Valley is set in a beautiful quite area. The property is suitable for 2 person, couples, …see more

from $46 / night

$321 / week

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from $46 / night

14

Vacation apartment in Ocho Rios

Saint Ann Parish / Ocho Rios

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 1 mi
  • Swimming pool
  • Car not necessary
Comfortable one bedroom apartment. Fully air conditioned and overlooking the warm waters of the aquamarine Caribbean Sea. Direct access to the beach or if you prefer ,a large swimming pool. Other amenities include water sports,Golf courses.boating and fishing. Within …see more

from $53 / night

$210 / week

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avg. 35 minutes

from $53 / night

(3) Very 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 $728 / night

$5096 - $6664 / week

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from $728 / 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 $122 / night

$853 / week

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Responds fast!
avg. 1 hour 7 minutes

from $122 / 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 $105 / night

$511 - $734 / week

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from $105 / night

37

Ocho Rios Vacation condo rental

Saint Ann Parish / Ocho Rios

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Ocho Rios is fast becoming the Tourist capital of Jamaica, once a small fishing village..it now has thousands of tourists from all over the world who come to experience what this unique Caribbean resort has to offer.. It has the World renowned Dunns River Falls on its d …see more

from $118 / night

$734 - $798 / week

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avg. 3 hours 35 minutes

from $118 / night

(1) Very Good 

14

Cottage rental in Negril Beach

Negril / Negril Beach

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Firefly is located on the famous seven miles beach in Negril Jamaica the only small Negril Hotel for couples, children and singles •Our friendly family and staff are here to invite you to be a part of our wonderful atmosphere. Step out of your cottage, apar …see more

from $120 / night

$945 / week

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from $120 / night

14

Vacation bungalow rental

Saint Ann Parish / Runaway Bay

3 4 3 nights min

  • 3 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Householder with special breakfast service in a secure and clean accommodation. It is for very favourable cost and a central start point for many activities. Support from natives will be offered. Beach is 10 minutes walking away so as shops and bus stop. Diving school a …see more

from $29 / night

$203 - $812 / week

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from $29 / night

(15) Very Good 

15

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 $46 / night

$321 / week

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from $46 / night

(1) Very Good 

Certificate of Excellence

26

Ocho Rios Vacation studio rental

Saint Ann Parish / Ocho Rios

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 1 mi
  • 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

Certificate of Excellence

from $53 / night

$328 - $413 / week

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Responds fast!
avg. 2 hours 24 minutes

from $53 / night

(3) Very Good 

24

Vacation condo 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
  • Swimming pool
  • Child friendly
Location Location Location...If you would like to stay at the best location in Ocho Rios..this is the condo to visit, this condo is so well located no need to spend money on taxi's everything is in walking distance, the golden beach is through the back entrance of the …see more

from $79 / night

$511 - $640 / week

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from $79 / 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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avg. 3 hours 13 minutes

from $100 / night

(3) Excellent 

15

Vacation 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 mi
  • 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 $66 / night

$361 - $531 / week

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avg. 1 hour 34 minutes

from $66 / night

(6) Very Good 

15

Vacation studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
This is a very romantic quiet peaceful resort, it's only ten minutes walk away from the shops, restaurants and tourist attractions. Beautiful self catering condo, with stunning sea and mountains view overlooking the bay of Ocho Rios. This property is set in 14 acres …see more

from $100 / night

$600 / week

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from $100 / night