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Vacation Rentals & Houses in Jamaica

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690 houses

Anticipation Villa at The Tryall Club

Sandy Bay villa

6 bedrooms / 7 bathrooms / sleeps 14

Match: Private outdoor pool (heated) Sea view Staffed property Golf course on site or within 15 min walk

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Price per night from

$2,831

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Sea Glass Villa

Hopewell villa

6 bedrooms / 8 bathrooms / sleeps 14

3 of 4 match: Sea view, Golf course on site or within 15 min walk, Private outdoor pool (heated), Staffed property

3 of 4 filters match

Price per night from

$2,339

Gated Apartment

Kingston apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 51 minutes

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$96

The Hillman Hideaway

Kingston apartment

1 bedroom / 1 bathroom / sleeps 4

2 of 4 match: Sea view, Private outdoor pool (heated), Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$117

Visit Glistening waters stay in Gated community

Falmouth villa

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 4 minutes

2 of 4 match: Private outdoor pool (heated), Staffed property, Golf course on site or within 15 min walk, Sea view

2 of 4 filters match

Price per night from

$59

Jamaica Villa Nutmeg, Montego Bay, Jamaica

Montego Bay villa

6 bedrooms / 6 bathrooms / sleeps 15

“Incredible view & fantastic staff” My family and I (7 adults & 1 child) just returned from Nutmeg Villa and we had a wonderful time!! Upon entering the Villa, there is a breathtaking view of the pool, the gardens and the sea which can't be beat. The rooms were spacious and suited our group well, especially the downstairs bedroom with the pool table and the games. We all agreed that the best aspects of our vacation were having a private pool and the staff at Nutmeg. The staff went above and beyond to make sure we were enjoying ourselves to the fullest and we did! On behalf of my family we would like to send a heartfelt thank you to Chef Morgan, Carlington, Ms. Ann, Ms. Cathy, Garrett, Wayne, Dave and Donovan (the security guard) for making our vacation unforgettable.

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$1,355

JAMAICA HILLTOP PARADISE (YOUR CASTLE AWAITS YOU)

Runaway Bay house

7 bedrooms / 6 bathrooms / sleeps 14

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$1,302

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$511

Beautiful Waterfront Studio

Negril studio

Studio / 1 bathroom / sleeps 2

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$144

Seven Palms Villa - Large open design, fresh water swimming pool, close to beach

Runaway Bay villa

4 bedrooms / 4 bathrooms / sleeps 10

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$600

Breathless Manor

Falmouth house

3 bedrooms / 3 bathrooms / sleeps 7

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$73

Pegasus

Runaway Bay villa

4 bedrooms / 4 bathrooms / sleeps 8

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$234

Cool shades gated estate

St. Ann's Bay house

3 bedrooms / 2 bathrooms / sleeps 6

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$126

Stunning 5 Star Ultra Luxe Jewel Grande Mobay Gold

Rose Hall condo

1 bedroom / 2 bathrooms / sleeps 4

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$239

Plantation Village 354 - Near Ocho Rios

Priory house

3 bedrooms / 4 bathrooms / sleeps 7

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$240

Rose Hall villa

4 bedrooms / 5 bathrooms / sleeps 8

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$840

Tennsville

Ironshore villa

4 bedrooms / 4 bathrooms / sleeps 8

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$323

Beautiful Luxury 1 BDRM Condo

St James, Montego Bay condo

1 bedroom / 1 bathroom / sleeps 3

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$172

Villa Turrasann

Runaway Bay villa

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 41 minutes

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$570

The Big White Villa Garden Suite[1bdr studio appt]

Tower Isle studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 26 minutes

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$84

Unit 105

Ocho Rios villa

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 46 minutes

2 of 4 match: Sea view, Private outdoor pool (heated), Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$648

Villa Sweet Villa, Montego Bay - 3 Spacious Ensuite Bedrooms

Ironshore villa

3 bedrooms / 4 bathrooms / sleeps 6

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$1,320

Happy Villa – The Splendor of Fairy Hill

Boston Bay house

2 bedrooms / 3 bathrooms / sleeps 4

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$76

Jetaway Montego Bay (Entire Villa)

Ironshore villa

11 bedrooms / 11 bathrooms / sleeps 25

Responds fast! avg. 2 hours 0 minutes

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$2,560

Cool's 1 Bedroom, Villa B6, On the Beach, Garden View, WiFi, Ground Floor

Ocho Rios apartment

1 bedroom / 1 bathroom / sleeps 4

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$123

SplashRock Ocean View Villa ( New Upgrades)

Negril villa

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 20 minutes

Travelers’ Choice award

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$72

Unit 103

Ocho Rios villa

3 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 1 hour 46 minutes

2 of 4 match: Sea view, Private outdoor pool (heated), Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$432

Unit 106

Ocho Rios villa

8 bedrooms / 9 bathrooms / sleeps 29

Responds fast! avg. 1 hour 46 minutes

2 of 4 match: Sea view, Private outdoor pool (heated), Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$1,566

Unit 102

Ocho Rios villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 46 minutes

2 of 4 match: Sea view, Private outdoor pool (heated), Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$324

Topaz Villa

Runaway Bay villa

4 bedrooms / 3 bathrooms / sleeps 6

2 of 4 match: Private outdoor pool (heated), Staffed property, Golf course on site or within 15 min walk, Sea view

2 of 4 filters match

Price per night from

$59

Blue sky villa,Seaside Resort

Negril house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 1 hour 6 minutes

Travelers’ Choice award

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$471

Serendipity Jamaica - You won't want to leave!

Rose Hall villa

6 bedrooms / 8 bathrooms / sleeps 12

“A vacation like no other” We were greeted at the airport by Norman, the most professional driver ever, he made our transition smooth and for a group of 12 adults, that is tough! He had thought of everything - including bringing a second van for our luggage! The staff at the villa greeted us at the door with warm smiles and cool towels, they made sure all our luggage was safely delivered to our rooms and then the fun began! We all stopped and stared at the huge view of the Caribbean Sea spread out in front of us, the breeze, the way the rooms are laid out and the villa itself takes total advantage of that view. We quickly changed, and began the most perfect seven days of nothing but relaxing, laughing and eating punctuated by an occasional sightseeing trip. Derek, the butler completely made the trip, he was attentive, but quiet, helpful but never intrusive - he made us feel so special. Ruby, the cook gave us gormet meals three times a day. We discussed our likes and dislikes the first day and she made it all happen. We did not need to go out to dinner and the one night we went to a lovely restaurant in town, we all agreed that we could have stayed home and eaten at Restaurant Ruby for an even better meal. It is tough to please 12 distinct people, but the staff and managment at Serendipity did just that, from organizing the most incredible massage at the villa, to driving us to out of the way Mayfield Falls, they never stopped working. All the rooms were large and private, we never felt on top of one another, we ate meals in different places, by the pool, in the dining room, on the deck, where ever we felt inspired to eat that day, Derek made it happen. I do not have one bad thing to say - I loved every minute, and would recommend Serendipity to a group like us, a large family, or just a few people that want to get away - It was truly a vacation to remember.

Travelers’ Choice award

3 of 4 match: Private outdoor pool (heated), Golf course on site or within 15 min walk, Sea view, Staffed property

3 of 4 filters match

Price per night from

$817

Heartease Suites 1

Kingston apartment

1 bedroom / 1 bathroom / sleeps 2

2 of 4 match: Sea view, Private outdoor pool (heated), Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$72

Luxury Life Villa

Priory villa

3 bedrooms / 2 bathrooms / sleeps 6

2 of 4 match: Private outdoor pool (heated), Staffed property, Golf course on site or within 15 min walk, Sea view

2 of 4 filters match

Price per night from

$288

Unwind at Richmond (near Ocho Rios)

Priory house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 58 minutes

2 of 4 match: Private outdoor pool (heated), Staffed property, Golf course on site or within 15 min walk, Sea view

2 of 4 filters match

Price per night from

$139

The Hugh Suite

Kingston apartment

1 bedroom / 1 bathroom / sleeps 2

2 of 4 match: Sea view, Private outdoor pool (heated), Golf course on site or within 15 min walk, Staffed property

2 of 4 filters match

Price per night from

$84

rose village

Rose Hall villa

5 bedrooms / 6 bathrooms / sleeps 11

3 of 4 match: Golf course on site or within 15 min walk, Private outdoor pool (heated), Sea view, Staffed property

3 of 4 filters match

Price per night from

$1,896

Flower Hill

Rose Hall villa

7 bedrooms / 7 bathrooms / sleeps 14

3 of 4 match: Golf course on site or within 15 min walk, Private outdoor pool (heated), Sea view, Staffed property

3 of 4 filters match

Price per night from

$3,505

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