50 Best Jamaica Estates on Holiday Lettings - Villas

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Saint James Parish
784 properties
Saint Ann Parish
650 properties
Kingston Parish
309 properties
Westmoreland Parish
207 properties
Trelawny Parish
165 properties
Saint Mary Parish
103 properties
Portland Parish
73 properties
Hanover Parish
49 properties
Saint Catherine Parish
47 properties
Saint Elizabeth Parish
37 properties
Manchester Parish
21 properties
Saint Andrew Parish
16 properties
Cabins Blue Mountains National Park
7 properties

Jamaica

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2,495 Vacation rentals

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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

$401 / week

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from $60 / night

(1) Excellent 

41

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 $87 / night

$434 - $732 / week

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from $87 / 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

$401 - $771 / week

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from $65 / night

12

Negril Vacation apartment rental

Westmoreland Parish / Negril

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
lovely clean apartment with all amenities. suitable for couples, quiet area close to city and beach. beautiful views.  …see more

from $34 / night

$235 / week

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from $34 / night

(1) Excellent 

16

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 $734 / night

$5138 - $6719 / week

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from $734 / night

20

Vacation villa with swimming pool in Mammee Bay

Saint Ann Parish / Mammee Bay

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Important Message. We love this place and are happy to leave it empty rather offer it to the wrong guests. Have a read of the information below and ask us some questions before you book. Sheer Folly is a fully staffed family owned luxury villa sitting an acre of lus  …see more

from $434 / night

$3100 / week

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from $434 / 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 $93 / night

$434 - $732 / week

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from $93 / night

(1) Good 

23

Vacation studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 1 night min

  • Studio
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
This fully furnished, ground floor, studio apartment, with wheelchair access and ensuite bathroom is located in a complex right on the beach, in the heart of Ocho Rios. This apartment has a king size bed, which has the flexibilty of being used as two singles. Sleep 2/3  …see more

from $51 / night

$348 / week

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from $51 / 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 o  …see more

from $69 / night

$770 - $772 / week

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from $69 / 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 $101 / night

$706 / week

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from $101 / night

(1) Excellent 

29

Villa rental in Port Antonio

Port Antonio / Williamsfield

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • 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&#  …see more

from $200 / night

$1400 / week

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from $200 / night

(2) 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

$459 / week

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from $75 / 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 $38 / night

$261 / week

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from $38 / 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 $76 / night

$484 / week

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from $76 / night

(2) Excellent 

13

Treasure Beach Vacation home rental

Saint Elizabeth Parish / Treasure Beach

5 8 2 nights min

  • 5 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly
The White House is located in Rose Hall St. Elizabeth, Jamaica. This holiday home is set 5km from Junction/Southfield. Lovers leap is 6km and 11km from Treasure beach. Be sure to check out the exclusive Pelican Bar and YS Falls as well as The Black River Safari Tours. T  …see more

from $186 / night

$651 / week

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from $186 / 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

$310 - $391 / week

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from $50 / night

(25) 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

$695 / 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 $72 / night

$495 - $682 / week

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from $72 / 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 $93 / night

$651 - $782 / week

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from $93 / night

(5) Excellent 

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 $116 / night

$808 / week

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from $116 / night

21

Villa rental in Silver Sands with swimming pool

Trelawny Parish / Silver Sands

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A spacious comfortable villa on the Silver Sands private, gated, villa estate. It is just 5 minutes walk from the beautiful white sand beach - considered one of the finest in Jamaica and is for the sole use of villa owners and guests. The villa has a private pool with  …see more

from $404 / night

$2521 / week

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from $404 / 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 $27 / night

$188 - $749 / week

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from $27 / 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

$501 - $900 / week

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from $100 / night

(3) Very Good 

35

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 $87 / night

$434 - $645 / week

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from $87 / night

(1) Good 

13

Kingston Vacation apartment rental

Kingston Parish / Kingston

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 9 mi
Planning a break in Jamaica? Experience the real Jamaica by choosing to be based in the heart of the islands' capital city, Kingston, in a really central location, near Devon House, Bon Marleys Museum and situated adjacent to the Canadian Embassy which is so easy  …see more

from $62 / night

$434 / week

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from $62 / 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 $56 / night

$372 / week

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from $56 / night

(1) Excellent 

20

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 $162 / night

$1130 / week

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from $162 / 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

(6) Very Good 

34

Ocho Rios Vacation condo rental

Saint Ann Parish / Ocho Rios

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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 $112 / night

$744 / week

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from $112 / night

(8) 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 $71 / night

$491 / week

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from $71 / night

20

Vacation apartment with shared pool in Tower Isle

Saint Mary Parish / Tower Isle

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Criss is a beautiful studio apartment, Apartment #3 at Chrisanns Beach Resort. Perfect for a relaxing getaway – a home away from home. Planning a Jamaican wedding and honeymoon? No Problem, mon! Everything can be done right here on property!! Chr  …see more

from $98 / night

$686 / week

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from $98 / night

(5) Very Good 

59

Vacation studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • 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

$695 - $1112 / week

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from $100 / 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 $147 / night

$958 / week

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from $147 / 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

$620 / week

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from $100 / night

(1) Excellent 

19

Home rental in Ocho Rios with shared pool

Saint Ann Parish / Ocho Rios

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
My place is close to family-friendly activities, public transport, 10 minutes drive to the beach and nightlife. You'll love my place because of its coziness, home away from home experience, the tranquility and well kept surrounding. My place is good for couples, so  …see more

from $81 / night

$565 / week

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from $81 / night

5

Vacation private room in Runaway Bay

Saint Ann Parish / Runaway Bay

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about children
  • Private garden
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 $27 / night

$188 - $375 / week

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from $27 / night

(1) Excellent 

46

Ocho Rios Vacation villa rental

Saint Ann Parish / Ocho Rios

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
If you've ever dreamed of paradise then Grande Haven Gibraltar is simply your ultimate dream come true. This modern and magnificently designed villa is nestled amidst a lush, tropically landscaped, palm tree-lined driveway, with dazzling ocean views of the famous J  …see more

from $505 / night

$3529 / week

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from $505 / night

(5) Very Good 

10

St James, Montego Bay Vacation condo rental

Montego Bay / St James, Montego Bay

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Swimming pool
WELL APPOINTED LUXURY 1BEDROOM APARTMENT ON JAMAICA'S GOLD COAST, ROSE HALL IS WITHIN 5 MINUTES FROM MONTEGO BAY AIRPORT. AMENITES INCL GRANITE COUNTER TOPS IN KITCHEN & BATHROOMS, BREATHTAKING VIEW FROM BALCONIES OF THE CARIBBEAN SEA/POOL AREA, OTHER ON PROPER  …see more

from $140 / night

$980 / week

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from $140 / night

(2) 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 $253 / night

$1765 - $3176 / week

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from $253 / 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 $36 / night

$222 - $494 / week

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from $36 / night