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Jamaica Rentals with Pools

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909 houses in Jamaica with pools

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.

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Price per night from

$313

The Marley manor

Kingston apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$125

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

$77

Shotover Gardens Estate - cottage with pool

Port Antonio log cabin

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$62

Sol Mar Villa

Silver Sands villa

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$413

Charming Villa with Swimming Pool & Beach Access

Runaway Bay house

5 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$390

Beach Studio with European Country Charm 15 Minute

Rose Hall apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$91

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

$169

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 16 minutes

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Price per night from

$344

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

$556

Sunrise Supreme

Runaway Bay apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 48 minutes

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Price per night from

$63

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!!!

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Price per night from

$518

Villa Gilgal - Possibilities Are Endless....

White House villa

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 31 minutes

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Price per night from

$1,144

Pleasant View Villa

Hopewell house

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$326

Grande Haven Villa - Oracabessa, St Mary Jamaica

Oracabessa villa

4 bedrooms / 5 bathrooms / sleeps 6

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Price per night from

$401

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!

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Price per night from

$96

Valhalla Villa

Boscobel villa

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$481

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

$258

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. 51 minutes

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Price per night from

$126

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

Rose Hall house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 49 minutes

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Price per night from

$988

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.

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Price per night from

$860

70 steps to the sand

Negril Beach condo

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$195

Serendipity Villa - Spectacular views of the Caribbean Sea

Treasure Beach villa

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$121

Luxury Ocean Front Villa 1 at Chukka Cove - The Perfect Tropical escape

Runaway Bay villa

3 bedrooms / 4 bathrooms / sleeps 7

Responds fast! avg. 2 hours 19 minutes

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Price per night from

$687

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

$625

Shotover Gardens Estate - cabin with pool

Port Antonio log cabin

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$37

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

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Price per night from

$327

Oceanfront 2 Bedroom 2 Bathrooms, Chef, Housekeeping, Pool

Ocho Rios apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$292

Gorgeous Oceanview Condo Montego Bay Jamaica

Montego Bay apartment

2 bedrooms / 3 bathrooms / sleeps 4

“A great place to stay!” We spent three wonderful days at alyssa's Condo in the heart of Montego Bay. It is in a quiet, gated community, with a 1 minute walk to Doctor's Cave beach. What more could you ask for? The condo is clean, and everything stated in her description is accurate. Alyssa is easily contacted and has a very pleasant demeanor. When we left her condo to continue the rest of our vacation in another parish, an iphone was left behind. Alyssa immediately contacted her cleaning lady and the iphone was left with the reception. We picked up the iphone 4 days later. Thank you alyssa for being so accommodating and we would definitely like to stay with you again on our next visit. Highly recommended!!

Match: Swimming pool

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Price per night from

$375

TNC Executive Villa at Richmond Estate Jamaica

Priory villa

3 bedrooms / 2 bathrooms / sleeps 6

“great location best holliday ever very clean well kept” we were blown away by the view mountains one side ocean the other pool and gym were great we rented a car to get around easy just a good thing for us as we stayed for 6 weeks wow ya man trevor was great and his rep on site was most helpful cant wait to go back

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$151

The Caymanas Villa

Portmore house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 37 minutes

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Price per night from

$93

Selah - Runaway Bay 4 Bedroom Beachfront

Runaway Bay house

4 bedrooms / 4 bathrooms / sleeps 8

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Price per night from

$1,698

Village Maria~ A true Jamaican villa experience Beachfront

Montego Bay house

4 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 20 minutes

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Price per night from

$973

Pelican Three Bedroom Villa

Treasure Beach villa

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$553

Tranquility Villa with Private Beach

Ocho Rios house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 10 minutes

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Price per night from

$138

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

Ocho Rios house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 37 minutes

Match: Swimming pool

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Price per night from

$116

Garden Oasis 3 bedroom Apt

Kingston apartment

3 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$218

Jim's Place - Garden Suite - Whitehouse,Westmoreland.

Bluefields apartment

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$69

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