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Jamaica Rentals with Pools

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1,324 houses in Jamaica with pools

Sunrise Supreme

Runaway Bay apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 34 minutes

Match: Swimming pool

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Price per night from

$57

Shotover Gardens Estate - cottage with pool

Port Antonio log cabin

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$58

Seadrift Villa w/ private pool, great entertainment space, easy walk to beach.

Duncans villa

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 0 minutes

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Price per night from

$312

Valhalla Villa

Boscobel villa

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$486

77 West Boutique Hotel (Cottage 1 of 5)

Treasure Beach cottage

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$151

Beach Studio with European Country Charm 15 Minute

Rose Hall apartment

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$81

Grande Haven Villa - Oracabessa, St Mary Jamaica

Oracabessa villa

4 bedrooms / 5 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$405

Riviera Villa in Mammee Bay, Jamaica - special event hosting

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 say more. The villa is spacious inviting and very clean, with air conditioning in each room. The pool is cleaned daily and is situated just of the veranda, easy to keep an eye on the young ones. It also has its own gate which can be locked to keep the younger child out if not supervised. The food which is prepared in the spacious kitchen is cooked to perfection. Some of the ingredients are taken off the property including herbs, mangos, bananas and other lustrous fruits and provisions. My party and l look forward to going to our home in the beautiful island of Jamaica. The private beach is just a short walk away where you can mingle and enjoy various cocktails and relax and enjoy the beautiful sunshine.

Match: Swimming pool

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Price per night from

$292

Island Treasure Villas

Ocho Rios house

3 bedrooms / 2 bathrooms / sleeps 8

“Great, beautiful villa with a great owner!!!!” The villa was just as beautiful as the pictures!! Also there was a miscommunication with the number of guests and the owner was very understanding and handled it promptly. He was very nice and was available when needed. I would recommend this villa 100%!!!

Responds fast! avg. 1 hour 13 minutes

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Price per night from

$128

Jamaica Luxury near the Beach

Bull Bay house

11 bedrooms / 11 bathrooms / sleeps 34

Responds fast! avg. 1 hour 50 minutes

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Price per night from

$69

Villa Gilgal - Possibilities Are Endless....

White House villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 24 minutes

Match: Swimming pool

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Price per night from

$955

Selah - Runaway Bay 4 Bedroom Beachfront

Runaway Bay house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$1,585

70 steps to the sand

Negril Beach condo

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$174

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 rented this beautiful treasure the week of my wedding to host a moderate group for our wedding rehearsal brunch and for me to have a place to relax away from the packed family home prior to the big day. The location was so breath taking that it was the ideal spot for us to film our pre-wedding video and take pictures as my bridesmaids and myself got ready for the main event. The garden was nicely manicured and looked beautiful. What I enjoyed best was sitting on the patio for breakfast enjoying the beautiful garden scenery as well as looking out at Kingston from the vantage point of this hidden treasure. At night the location took on a magical ambience as I enjoyed the lights of the city from standing on the patio and the stars in the sky while listening to music softly in the background. The neighborhood is quiet and at times you can forget that anyone else lives around you as Signature's 21 makes you feel like you are on your own island paradise. My guests who came for the rehearsal brunch all fell in love with Signature's 21. I hope to visit again soon and I am sure that a few of my guests will too. Thank you Bancroft for sharing your garden treasure with us. I wish you continued success with Signature's 21 @ the Country Club!

Responds fast! avg. 30 minutes

Match: Swimming pool

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Price per night from

$80

North Coast Escape - Drax Hall, Ocho Rios, St. Ann

Ocho Rios house

3 bedrooms / 2 bathrooms / sleeps 6

“Best time of our lives” We cannot wait to come back and visit again!!!! We came for our borthdays, we were treated very well. The house was amazing. The owner was very accomidating.

Responds fast! avg. 53 minutes

Match: Swimming pool

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Price per night from

$107

Village Maria~ A true Jamaican villa experience Beachfront

Montego Bay house

4 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 14 minutes

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Price per night from

$750

The Marley manor

Kingston apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$70

Villa @ Richmond Estate with Private Beach

Priory house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 47 minutes

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Price per night from

$231

Award-winning villa with private beach and pool

White House villa

5 bedrooms / 4 bathrooms / sleeps 10

“Wow!” We stayed as a family of 6 adults in September & had the time of our life! Andy the owner is really easy to do business with & communicates well. The location is superb with its own small private beach as well as an infinity pool. The grounds are spectacular with fruit trees, abundant flowers and many different species of birds. The housekeepers (Dion & Lilly) are superb cooks & hosts, their food was top drawer restaurant standard the whole time we were there. Karon the caretaker / gardener is an interesting guy & is really knowledgeable when it comes to the plants in the garden. Mervyn provided the night security which was discreet & appreciated. We are already saving hard to go again next year (but for longer)! Thank you andy & the team!

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Price per night from

$632

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: Swimming pool

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Price per night from

$463

The Caymanas Villa

Portmore house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 11 minutes

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Price per night from

$93

Nautical Homes Miramar

Montego Bay house

3 bedrooms / 3 bathrooms / sleeps 6

“Holiday Home” My daughter and I rented this really beautiful villa. Angie collected us from the airport and kindly took us shopping to get some food to tide us over until we picked up our rented car. The house smelled fresh as we walked in. The lounge is spacious with three and two seater settees, coffee table and a large smart TV on the wall. The villa has air-conditioning in the lounge and both bedrooms that was much appreciated as it was sometimes 35 degrees outside. Bedrooms have TVs on the wall. There is a large round thick glass dining table with 4 chairs. The kitchen has a fridge-freezer, gas cooker, microwave, kettle, coffee maker, toaster and a washing machine that my daughter thought wonderful as she used it often. Everything is as described in respect of this villa. We had a wonderful stay and will definitely return when next in Jamaica. Another thing we thought wonderful is the automatic gates - no getting out and opening the gate - just press the remote control, drive in and park! The security company checked the house and left a note to say they have been round. We felt very safe at the villa. If you do not rent a car, Bouge taxis can be found who will take you where you want to go or ask Angie. There is a very smart car for rental should you need it at the villa. We did not hire this car as we had previously booked a 4 x 4 to take us cross country to St. Catherine and other areas that had rough terrain. We were not bothered by anyone - complete freedom. Well done Vinroy. Best wishes Dorothy and Adella.My Response Thank you very much for that wonderful review! Looking forward to having you and your daughter again. Thanks much

Responds fast! avg. 19 minutes

Match: Swimming pool

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Price per night from

$339

Ocean Front Villa 1 at Chukka Cove

Runaway Bay villa

2 bedrooms / 3 bathrooms / sleeps 5

Responds fast! avg. 2 hours 0 minutes

Match: Swimming pool

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Price per night from

$238

Home Away from Home 15 mins fr Ochi Rios

Boscobel house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$85

Sol Mar Villa

Silver Sands villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 43 minutes

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Price per night from

$348

Hummingbird Hill Villa, Full Staff Included

Runaway Bay villa

5 bedrooms / 5 bathrooms / sleeps 12

Match: Swimming pool

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Price per night from

$457

TNC Executive Villa at Richmond Estate Jamaica

Priory villa

3 bedrooms / 2 bathrooms / sleeps 6

“Simply Amazing” Excellent is an understatement. My stay at TNC Executive Villa was Amazing. Management was superb. Jhoval thanks for the great hospitality. See you soon.

Responds fast! avg. 10 minutes

Match: Swimming pool

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Price per night from

$124

Oceanfront 2 Bedroom 2 Bathrooms, Chef, Housekeeping, Pool

Ocho Rios apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$261

Shotover Gardens Estate - cabin with pool

Port Antonio log cabin

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$35

Tranquility Villa with Private Beach

Ocho Rios house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 8 minutes

Match: Swimming pool

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Price per night from

$139

Paradise Plum - 4BD,Pool, Ocean views, full staff

Rose Hall house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 14 minutes

Match: Swimming pool

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Price per night from

$868

Pelican Three Bedroom Villa

Treasure Beach villa

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$572

2-br watervu apt-Seawind onthe Bay,Montego Bay,Jam

Montego Bay apartment

2 bedrooms / 2 bathrooms / sleeps 5

Match: Swimming pool

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Price per night from

$203

Shakti Home-The villa you've been dreaming about

Treasure Beach villa

3 bedrooms / 3 bathrooms / sleeps 6

“The best the best the best” We traveled with our 4 children and my mother in law to Treasure Beach for the week. It was absolutely Phenomenal. It is perfectly situated On the beach with two magnificent beach coves 20 steps from the door. Our kids were able to run in and out easily all day. Absolutely highlight however is audrey's fantastic cooking. We made a menu with her for the week and every night after a heavenly day at the beach we were greeted with a traditional, home cooked Jamaica Feast. Book early because this house books up far in advance.

Match: Swimming pool

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Price per night from

$562

Beautiful Staffed Villa with Spectacular North Shore Ocean Views

Ocho Rios villa

3 bedrooms / 4 bathrooms / sleeps 12

“Perfect Vacation Spot” Spectacular views. House is wonderful. Staff is awesome. Could not have been more accommodating. Sharon's meals were awesome. Cutty, our driver is an invaluable resource of information. Will definitely go back

Responds fast! avg. 2 hours 53 minutes

Match: Swimming pool

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Price per night from

$330

Villa BiancaJel, 8 mins from Ocho Rios, a/c, pool, mountain view

Ocho Rios house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 38 minutes

Match: Swimming pool

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Price per night from

$116

Serendipity Villa - Spectacular views of the Caribbean Sea

Treasure Beach villa

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 16 minutes

Match: Swimming pool

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Price per night from

$116

Pleasant View Villa

Hopewell house

3 bedrooms / 4 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$322

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