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Jamaica Rentals with Pools

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Jamaica Rentals with Pools

1,271 vacation rentals

Pavilion Villa

Saint James Parish villa

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,214

1 / 15

Sunrise Supreme

Runaway Bay apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$52

1 / 13

Spanish Cove

Saint Ann Parish villa

4 bedrooms / 4 bathrooms / sleeps 7

Price per night from

$880

1 / 37

Cozy Cove - 5 Bdrm Villa w/Pool, Gated Community

Montego Bay villa

5 bedrooms / 5 bathrooms / sleeps 10

“Jamaican Paradise!” Cannot truly express how fabulous this trip has been, Jaime from the very beginning has been gracious, warm and very accommodating. Her rental has been nothing but spectacular! It is exactly and more than what the pictures convey.

Price per night from

$892

1 / 33

Seven Seas

Saint Ann Parish villa

4 bedrooms / 4 bathrooms / sleeps 9

“Fantastic!” What a fantastic time we all just had at Seven Seas! Our whole family enjoyed the trip from young to old. Not only was the estate gorgeous, but activities abounded on the property. The snorkeling we were able to enjoy in our own backyard w

Price per night from

$1,000

1 / 34

Sun Kissed - Rio Bueno 4 Bedroom Beachfront

Discovery Bay house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$779

1 / 19

Beach Studio with European Country Charm 15 Minute

Rose Hall apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$70

1 / 14

Grande Haven Villa - Oracabessa, St Mary Jamaica

Oracabessa villa

4 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 2 hours 10 minutes

Price per night from

$397

1 / 35

The Marley manor

Kingston apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$109

1 / 13

Riviera Wellness Retreat, Mammee Bay villa, JM

Mammee Bay villa

3 bedrooms / 4 bathrooms / sleeps 6

“Riviera Villa is like living in paradise with beautiful people.” My party and I have been visiting our holiday home as we like to call it for the last 13 years. In recent years we have gone twice. The staff have become apart of our own family. Need l

Price per night from

$251

1 / 14

Bolt House

Saint Mary Parish villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$2,400

1 / 34

Signature's 21 @ the Country Club

Kingston apartment

1 bedroom / 1 bathroom / sleeps 3

“Signature's 21 @ the Country Club was the icing on the cake for my Simply Elegant Wedding Celebration.” The owner and caretaker of Signature's 21 @ the Country Club were both patient, kind and accommodating to our needs from booking to departure. I r

Responds fast! avg. 1 hour 21 minutes

Price per night from

$69

1 / 35

Jamaica Luxury near the Beach

Bull Bay house

11 bedrooms / 11 bathrooms / sleeps 34

Price per night from

$85

1 / 14

Goat Hill

Hopewell villa

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$1,000

1 / 73

Sugar Bay - Jamaica

Discovery Bay villa

5 bedrooms / 6 bathrooms / sleeps 10

“Sugar Bay” I have been to Sugar Bay twice with my all girls tennis and bridge group. Sugar Bay is a gorgeous, upscale villa where you feel right at home! Reds, the wonderful houseman, is a delight and makes sure you have everything you need. The cook

Price per night from

$2,032

1 / 22

Contemporay Central Spacious 2bdrm/2bth/Pool/Toni Comfort Suites

Kingston apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 6 minutes

Price per night from

$140

1 / 42

Siesta

Runaway Bay villa

5 bedrooms / 5 bathrooms / sleeps 12

“"No problems..Irie!"” A large group of friends and myself have stayed here at Siesta several times. Although I have not been back since the late 80's, others of our group continue to go there just about every year. What I can say is that my time spent

Price per night from

$829

1 / 17

Anticipation - Tryall Club

Hopewell villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$2,241

1 / 22

Tangerine Villa, Exclusive With Full Staff, Members Beach, Fabulous Ocean Views

Runaway Bay villa

7 bedrooms / 7 bathrooms / sleeps 16

Price per night from

$996

1 / 27

Karma Bay - Tryall Club

Hopewell villa

6 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$2,214

1 / 14

4 Bedroom Villa Across from Beach in Bluefields.

Bluefields house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$70

1 / 19

Seaesta Villa

Boscobel house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$322

1 / 67

Chilling on the Estate

Kingston house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$80

1 / 17

70 steps to the sand

Negril Beach condo

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$150

1 / 9

Infinity - Tryall Club

Hopewell villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$2,091

1 / 17

Hummingbird Hill Villa

Runaway Bay villa

5 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 3 hours 4 minutes

Price per night from

$496

1 / 26

A Summer Place

Discovery Bay villa

7 bedrooms / 9 bathrooms / sleeps 14

Price per night from

$1,714

1 / 33

Pelican Three Bedroom Villa

Treasure Beach villa

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$493

1 / 8

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

Price per night from

$397

1 / 32

77 West Boutique Hotel (Cottage 1 of 5)

Treasure Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$130

1 / 10

4 bedroom cottage w/pool in Whitehouse, Jamaica

White House house

4 bedrooms / 4 bathrooms / sleeps 9

“From start to finish, we felt like we were indulging all our sen” La Vista is the perfect vacation spot if you are looking for a get away and wish to experience true Jamaican lifestyle away from the hustle of more touristy locations. It is situated o

Price per night from

$674

1 / 23

Villa @ Richmond Estate with Private Beach

Priory house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 5 minutes

Price per night from

$98

1 / 20

Valhalla Villa

Boscobel villa

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$395

1 / 15

Cary Island

Tower Isle villa

7 bedrooms / 7 bathrooms / sleeps 14

Price per night from

$1,210

1 / 17

Pleasant View Villa

Hopewell house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 43 minutes

Price per night from

$276

1 / 20

Private Beach Condo, Pool, Jacuzzi, Private Chef and Housekeeping

Ocho Rios apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$150

1 / 33

Island Treasure Villas

Ocho Rios house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 31 minutes

Price per night from

$110

1 / 68

Seagrapes - Jamaica

Discovery Bay villa

6 bedrooms / 6 bathrooms / sleeps 10

“Dream Vacation” We had a marvelous, fun-filled, and restful vacation in at Sea Grapes Everyone in our party was a little bit heartbroken when we had to go home I think! The accomadations were all that we had hoped for and the property and views were b

Price per night from

$1,086

1 / 25
Viewing 38 of 1,271
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