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Vacation Rentals & Houses in Jamaica

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31 houses

Shotover Gardens Estate - cottage with pool

Port Antonio log cabin

1 bedroom / 1 bathroom / sleeps 2

Match: Private outdoor pool (heated)

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Price per night from

$58

Villa Gilgal - Possibilities Are Endless....

White House villa

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 4 minutes

Travelers’ Choice award

Match: Private outdoor pool (heated)

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Price per night from

$1,089

The Biggest and Best on Jamaica's South Coast

White House villa

5 bedrooms / 7 bathrooms / sleeps 10

“Best Vacation Ever!” My family and I stayed at Point Of View Villa last Christmas. We had a fantastic time! The Villa was beautiful and the staff was extremely nice and helpful. It was wonderful to find a place away from all the tourist traps and high prices, but still be able to take short trips to see many of Jamaica's attractions. My family and I are definitely coming back! Having our own private cook was great, we all loved her cooking and professional service, it was more than we had hoped for. We have stayed other places and this was by far the best. The owner was very helpful advising us. Highly recommended!!!

Match: Private outdoor pool (heated)

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Price per night from

$491

Out of the Blue Villa

Treasure Beach villa

4 bedrooms / 5 bathrooms / sleeps 8

“Paradise!!!” The most amazing vacation we have ever had!! The house and beach were spectactular, the staff were knowledgeable, friendly and kind, and the food was incredible. The whole family loved it. We only booked for a week but will be coming back for at least 2 weeks next year.

Match: Private outdoor pool (heated)

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Price per night from

$885

DUKES Hideaway at Silver Sands Resort

Silver Sands villa

6 bedrooms / 6 bathrooms / sleeps 14

“Totally elaxing and worth it!” This was the fourth year that my family has stayed at Duke's Hideaway. We have 2 girls now ages 7 and 10 and we also bring my father who is 78. The location is very convenient to the grill, bar and store. It is also convenient to the beach. We love Judith and Paulina who help at the house and they remember us and the girls each year we have come. They cook delicious food for all of us and it is so nice not to have to eat out every day. One of the best conveniences staying at Duke's is that your laundry is done daily and when you get home, we don't have a bunch of laundry to do. We just come home and unpack our clean clothes! We feel like they are a part of our family when we are staying there. We also love staying there because it is very relaxing and it feels like a true vacation. Each year we have stayed at Duke's there has been some kind of improvement added to the house. There is a hot tub, air conditioning, televisions in each room and Wi-Fi. We have always felt very safe and welcomed at Silver Sands and at Dukes Hideaway.

Responds fast! avg. 3 hours 19 minutes

Match: Private outdoor pool (heated)

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Price per night from

$1,140

Montego Bay villa

5 bedrooms / 5 bathrooms / sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$1,379

Montego Bay Villa, View of Caribbean Sea

St. Ann's Bay apartment

1 bedroom / 7 bathrooms / sleeps 2

Match: Private outdoor pool (heated)

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Price per night from

$99

Round House at the Tryall Club

Montego Bay villa

8 bedrooms / 10 bathrooms / sleeps 16

Match: Private outdoor pool (heated)

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Price per night from

$2,297

Pineapple Cottage The Hidden Gem

Silver Sands cottage

2 bedrooms / 2 bathrooms / sleeps 5

“An incredibly relaxing vacation” This was our 6th visit to Pineapple at Silver Sands. We go instant relaxation mode as soon as we get off the plane. The staff are all incredibly friendly and helpful. The food is great, the place is lovely and clean, and the weather is fabulous.

Responds fast! avg. 3 hours 19 minutes

Match: Private outdoor pool (heated)

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Price per night from

$387

Bolt Hole Villa

Port Antonio villa

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$667

Pineapple Villa

Duncans villa

7 bedrooms / 8 bathrooms / sleeps 14

“Our annual Guilty Pleasure” If you have read my previous reviews, you know that we think that a vacation at Pineapple Villa is perfection. This year we were there for 2 whole weeks and I was worried that it might be a bit too long, well I was sooo wrong, I didn't want to go home. It's very easy to get used to a carefree life with no decisions to make except whether you want to swim in your own pool or go to the beautiful beach where there are very few people. I can sit on the patio and gaze at the ever changing colours of the sea for hours without ever getting tired of it. The Villa itself is cleaned thoroughly inside and out daily, each meal is tastier than the last and the wonderful staff are now like old friends. Every year we return to a new surprise. This year was the addition of flat screen Tv's with satellite in each bedroom. There were already Tv's in each of the 3 living rooms but I must say that it was nice to be able to keep up with our favorite shows . Since our group is getting smaller we are going to have a new experience next year staying in a brand new villa being built by the same owner. It is 31 metres from the beach and will have it's own infinity pool, great views and most importantly familiar staff! Can't wait!

Responds fast! avg. 3 hours 19 minutes

Match: Private outdoor pool (heated)

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Price per night from

$1,134

Fairway Manor

Montego Bay villa

7 bedrooms / 9 bathrooms / sleeps 16

Match: Private outdoor pool (heated)

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Price per night from

$1,576

Sea Salt at the Tryall Club

Montego Bay villa

5 bedrooms / 6 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$1,671

Birdie ‘ill Villa

Port Antonio villa

4 bedrooms / 3 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$788

Sunset on the Beach at the Tryall Club

Montego Bay villa

5 bedrooms / 5 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$1,746

Roaring Pavilion - Ultimate Luxury Beachfront Villa

Ocho Rios villa

5 bedrooms / 5 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$3,191

Sea Glass Villa

Hopewell villa

6 bedrooms / 8 bathrooms / sleeps 14

Match: Private outdoor pool (heated)

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Price per night from

$2,392

VILLA DORA MAE

Mammee Bay villa

6 bedrooms / 6 bathrooms / sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$1,136

Rose Cottage at the Tryall Club

Montego Bay villa

6 bedrooms / 8 bathrooms / sleeps 14

Match: Private outdoor pool (heated)

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Price per night from

$2,089

Serenity on the Beach

Montego Bay villa

4 bedrooms / 4 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$1,044

Island Breeze Villa

Montego Bay villa

3 bedrooms / 1 bathroom / sleeps 6

Match: Private outdoor pool (heated)

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Price per night from

$351

Willows villa

St. Ann's Bay villa

2 bedrooms / 2 bathrooms / sleeps 4

Match: Private outdoor pool (heated)

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Price per night from

$301

*PLEASE ENQUIRE FOR SPECIAL RATES* Luxury 5 Bed Fully Staffed Beachfront Villa

Discovery Bay house

5 bedrooms / 6 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$1,259

Serenity on the Beach - 4 Bedroom Villa at Montego Bay - Book Now

Hopewell villa

4 bedrooms / 4 bathrooms / sleeps 8

Match: Private outdoor pool (heated)

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Price per night from

$1,259

*PLEASE ENQUIRE FOR SPECIAL RATES* Luxury 5 Bed Fully Staffed OceanFront Villa

Montego Bay villa

5 bedrooms / 5 bathrooms / sleeps 10

Match: Private outdoor pool (heated)

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Price per night from

$1,121

*PLEASE ENQUIRE FOR SPECIAL RATES* 5 Bedroom Fully Staffed Villa with Ocean View

St James, Montego Bay villa

5 bedrooms / 4 bathrooms / sleeps 12

Match: Private outdoor pool (heated)

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Price per night from

$1,288

Match: Private outdoor pool (heated)

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Price per night from

$1,087

rose village

Rose Hall villa

5 bedrooms / 6 bathrooms / sleeps 11

Match: Private outdoor pool (heated)

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Price per night from

$1,940

Flower Hill

Rose Hall villa

7 bedrooms / 7 bathrooms / sleeps 14

Match: Private outdoor pool (heated)

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Price per night from

$3,586

Anticipation Villa at The Tryall Club

Sandy Bay villa

6 bedrooms / 7 bathrooms / sleeps 14

Match: Private outdoor pool (heated)

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Price per night from

$2,896

6 ACRES, 6 BEDROOMS, TENNIS COURTS, HUGE POOL!

Montego Bay villa

6 bedrooms / 6 bathrooms / sleeps 12

“So great I already booked next year” Sorry guys the 14-21 of May is ours.I encourage anyone whose reading this to snag one of the other weeks. Absolutely the only way to travel. I work long hours in a hectic industry, I take any free time with my family very serious. Our party was my mother, my sister, her son, my wife our two children and myself . Everybody had a wonderful vacation. The property is magnificent. The grounds are impeccable. The house is decorated masterfully. Every bathroom is unique and awe inspiring, and showering outside under the stars is the perfect way to end the night. But the thing that words really can't describe is the staff. The professionalism and attention to detail was absolutely remarkable, but the warmness and caring was what makes the difference. If my two year old would get cranky, there'd be Dalton with ice cream cone for him and a red stripe for dad. Juanita had everything in order at all times and everything tended to immediately. Brenda's cooking was amazing. The groundskeepers kept the grounds perfect and the pool clean and would even chill coconuts, right from the property, for our enjoyment. Every afternoon our clothes were dropped off cleaned, pressed and folded and the house was always immaculate. I recommend getting the driver and the van for the week. Lloyd was both professional and informative. Truly a great time for three generations of family. As I said at the opening we already booked next year, that should speak for itself. Grady Bergen County New Jersey

Responds fast! avg. 3 hours 45 minutes

Match: Private outdoor pool (heated)

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Price per night from

$1,424

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