50 Best Jamaica Estates on Holiday Lettings - Villas

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Saint James Parish
821 properties
Saint Ann Parish
669 properties
Kingston Parish
316 properties
Westmoreland Parish
211 properties
Trelawny Parish
167 properties
Saint Mary Parish
108 properties
Portland Parish
68 properties
Hanover Parish
48 properties
Saint Catherine Parish
46 properties
Saint Elizabeth Parish
37 properties
Manchester Parish
20 properties
Saint Andrew Parish
16 properties
Cabins Blue Mountains National Park
7 properties

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2,568 Vacation rentals

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(26) 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 ACCESSThe Apartment is tastefully furnished to a high standard, within the  …see more

from $100 / night

$700 / week

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from $100 / 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, rap  …see more

from $313 / night

$2125 / week

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from $313 / 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  …see more

from $100 / night

$625 / week

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from $100 / night

(1) Excellent 

23

Vacation 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 only 20 minutes from the legendary Dunn's Rivers Falls, and only 25 minutes to Jimmy Buffet's Margueritaville Restaurant and Beach Bar,and The Hard Rock Cafe in Ocho Rios.There are four large air-conditioned bedrooms, each with its own bat  …see more

from $285 / night

$1995 / week

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from $285 / 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 $35 / night

$220 - $490 / week

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from $35 / night

(3) Good 

18

Vacation 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
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;  …see more

from $100 / night

$500 - $900 / week

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from $100 / 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'  …see more

from $73 / night

$499 - $688 / week

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from $73 / night

(10) Very Good 

37

Runaway Bay Vacation 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 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

from $70 / night

$490 / week

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from $70 / night

(3) Very Good 

15

Vacation apartment in Ocho Rios

Saint Ann Parish / Ocho Rios

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
Imagine an apartment a which has fabulous views, in a quiet location. This is a superb 2 bedroom holiday apartment in a quiet location yet minutes away from the fun and activities which the Ocho Rios scene can offer! 'Reggae Beach', Jet Ski rentals, mountain,  …see more

from $49 / night

$325 / week

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from $49 / 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

(5) Excellent 

23

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 0.2 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  …see more

from $100 / night

$600 / week

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from $100 / night

(1) Good 

7

Negril Vacation apartment rental

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 pri  …see more

from $130 / night

$840 / week

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from $130 / 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  …see more

from $65 / night

$400 - $770 / week

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from $65 / night

(2) Excellent 

33

Tower Isle Vacation apartment rental

Saint Mary Parish / Tower Isle

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Sea Palms E3 is a delightful holiday apartment in the gated holiday complex of Seas Palms along the coastline between the town of Ocho Rios and Tower Isle. Free Wi-Fi broadband internet is included. The 1st floor (American 2nd floor) apartment offers three bedrooms, two  …see more

from $188 / night

$1125 / week

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from $188 / night

(31) Very Good 

77

Vacation 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 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 This villa is located in the prestigious Mammee Bay Estate  …see more

from $188 / night

$1125 / week

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from $188 / night

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

(3) Excellent 

24

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
  • 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

from $47 / night

$300 - $375 / week

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from $47 / night

(1) Excellent 

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

(9) Excellent 

22

Vacation villa in Treasure Beach

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 $59 / night

$412 - $832 / week

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from $59 / night

(1) Excellent 

15

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 Miss Iris, assistant Sandra, Curtis gardener and Johnny our experien  …see more

from $160 / night

$1120 / week

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from $160 / night

(1) Very Good 

20

Ocho Rios Vacation apartment rental

Saint Ann Parish / Ocho Rios

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Ask about 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), you  …see more

from $57 / night

$375 / week

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from $57 / night

(2) Very Good 

24

Vacation villa in Mammee Bay

Saint Ann Parish / Mammee Bay

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Morning Glory Villas occupies 1.5 acres of beautifully manicured tropical garden is just a stroll (2 minute) from the beautiful private Mammee Bay beach with its powdery soft sands and beach club. This large property "Over the Moon" and "Sanora&qu  …see more

from $132 / night

$919 / week

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from $132 / night

24

Villa rental in Jamaica with swimming pool, golf nearby

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  …see more

from $1734 / night

$12138 - $15897 / week

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from $1734 / 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 insid  …see more

from $188 / night

$1313 / week

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from $188 / night

(8) Excellent 

27

Vacation apartment with golf nearby in Kingston

Kingston Parish / Kingston

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Air conditioning
The Pentwood is a newly renovated apartment with everything brand spanking new!!!!. It's decorated in a modern ultra chic style, with beautiful lighting, wooden blinds, wooden floors, air conditioning, modern kitchen appliances, a classy modern bathroom, and a comf  …see more

from $82 / night

$490 / week

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from $82 / night

(6) Excellent 

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

from $94 / night

$657 - $788 / week

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from $94 / night

(10) Very Good 

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

from $47 / night

$300 - $375 / week

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from $47 / night

(3) Very Good 

20

Vacation apartment with shared pool, golf nearby in Runaway Bay

Saint Ann Parish / Runaway Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Club Caribbean Court Apartment is ideally located in a great location in Runaway Bay Jamaica.Located steps from the Royal Decameron,the apartment has all amenities for self catering.There is a separate bedroom with ensuite bathroom,kitchen and living area.The b  …see more

from $65 / night

$455 / week

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from $65 / 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 $63 / night

$338 - $507 / week

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from $63 / night

(11) 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 th  …see more

from $79 / night

$553 / week

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from $79 / night

(7) Very Good 

26

Vacation 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 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  …see more

from $117 / night

$814 / week

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from $117 / night

(2) Very Good 

29

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 $94 / night

$438 - $738 / week

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from $94 / night

(1) Excellent 

24

Vacation villa rental

Saint James Parish / Montego Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Scotch on the Rocks a stunning 5 bedroom ocean front villa with wonderful views of the Caribbean Sea, just minutes from lively Ocho Rios.Scotch on the Rocks is a charming 5 bedroom villa overlooking the Caribbean Sea. Its ideal location is a privately  …see more

from $934 / night

$6535 - $10035 / week

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from $934 / night

(2) 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 $82 / night

$488 - $563 / week

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from $82 / 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 $700 / night

$4900 / week

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from $700 / night

(1) Very Good 

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

from $50 / night

$313 - $394 / week

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from $50 / 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  …see more

from $75 / night

$488 - $610 / week

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from $75 / night

(2) Excellent 

13

B&b rental in Negril

Westmoreland Parish / Negril

7 12 2 nights min

  • 7 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
Private elegant set in a lush tropical garden in a quiet residential area off Negril's west end, Nelsons Retreat is close to Negril town Centre and its gorgeous seven-miles stretch of palm fringed beach. it is also far away enough to give you a perfect feeling of  …see more

from $500 / night

$3200 / week

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from $500 / night

(4) Excellent 

33

Vacation 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 $199 / night

$1750 - $3570 / week

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from $199 / night

(5) Very Good 

59

Vacation studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Jamaica is one of the best kept secrets in In the Caribbean. Sandcastles Ocho Rios Resort is the Ultimate vacation destinaion uncovered at your fingertips. This spacious studio apartment comes with FREE Wifi for internet access, kettle microwave and fridgefreezer to c  …see more

from $100 / night

$700 - $1120 / week

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from $100 / 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.