Vacation Rentals & Houses in Jamaica

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Penthouse In Paradise, 3 bdrm incl. housekeeper

Montego Bay apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 0 minutes

1 of 3 match: Shared outdoor pool (heated), Private pool, Swing set or jungle gym

1 of 3 filters match

Price per night from

$373

Honeycomb Villa, Silver Sands

Silver Sands villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$614

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$917

TEST PROPERTY

Port Royal chalet

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$246

Villa by the Cove

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Shared outdoor pool (heated), Private pool, Swing set or jungle gym

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Price per night from

$287

Coolshade Villa - Richmond - Ocho Rios

Ocho Rios villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Shared outdoor pool (heated), Private pool, Swing set or jungle gym

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Price per night from

$207

Village Maria~ A true Jamaican villa experience Beachfront

Montego Bay house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$861

Villas Sur Mer (1-Bedroom)

Negril cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Private pool, Swing set or jungle gym, Shared outdoor pool (heated)

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Price per night from

$474

Casa Bella Villa

Rose Hall villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$804

The Havendale Vacation Haven

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Shared outdoor pool (heated), Private pool, Swing set or jungle gym

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Price per night from

$75

Nickel's Garden Villas

Montego Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 3 match: Shared outdoor pool (heated), Private pool, Swing set or jungle gym

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Price per night from

$117

Calming Waters Riverside Villa & Yoga Retreat

Montego Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$201

Luxury Villas with Beautiful Ocean Views

Ocho Rios villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$896

Shotover Gardens Estate - cottage with pool

Port Antonio log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$58

Shotover Gardens Estate - cabin with pool

Port Antonio log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Private pool, Swing set or jungle gym, Shared outdoor pool (heated)

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Price per night from

$35

3BD Villa Including Housekeeper/ Airport Transfers

St. Ann's Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Shared outdoor pool (heated), Private pool, Swing set or jungle gym

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Price per night from

$207

Zyani Boutique Resort Voted #1 Seaside Villa in Ocho Rios Jamaica

Rio Nuevo villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$689

Whistling Villa-Most Affordable Private Villa with pool In Runaway Bay Jamaica

Runaway Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Affordable, spacious and near luxurious.” Visited Whistling Villa May 16th - 23rd with 4 friends. I chose this villa primarily because of proximity to attractions in Ocho Rios and Runaway Bay. Osburn always responded to my emails within minutes of sending them, which was comforting. I stayed at another property owned by him, and therefore trusted him. General: The villa was almost too large for 5 friends, but we each had our own space. The layout of the villa maximized the space so that the living area was extremely large. It was clean and well decorated but not so much so that you are aware that you're on an island villa; it had a really cozy feeling. Housekeeper: We had a cook!! We begged her to come home with us. Dorothy made everything we asked for and on the days we asked her to surprise us, we had heavenly meals! Breakfast was always prompt and we had breakfast in the outdoor dining area near to the pool. Pool: At the deepest end, the pool was 8ft deep. It was large and with 5 of us in the pool at the same time, we were not crowded. Bedrooms: The bedrooms were large with en suite bathrooms, a small television with cable TV, closet, air condition and dresser. It was clean and cozy. The bed sheets were outdated, but who goes to Jamaica to stay in bed right? Groundskeeper: Chris, who's the grounds man, kept the property clean and most mornings when he woke up to rake the grass, I interrupted him for some chit chat. He's soft spoken and extremely helpful, always asking if we needed anything. Amenities: We celebrated one birthday while there, and needed some music, but the reception on the radio was a bit poor and had static, so walk with many CDs. Wifi was strong in most areas, but weakest in the bedrooms. Appliances were as expected for an island villa.

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$230

Scotch on the Rocks Villa, Ocho Rios, Jamaica

Ocho Rios villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

“Great Family Vacation” Excellent facilities, wonderful staff with extraordinary cook, food exceeded expectations as well as accommodating children's requests. Pool, kayaks and snorkeling gear provided, we took kids fins and goggles. Would not hesitate to return.

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$2,005

Jamaica Villa Nutmeg, Montego Bay, Jamaica

Montego Bay villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

“Being in Paradise” The Villa was more than I could have Dreamed!! My friends and I decided to take a trip and then experience was breathe taking. The staff made us feel like Kings and Queens and it was AMAZING. I highly recommend if travel with a large group!

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

1 of 3 filters match

Price per night from

$1,607

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.

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$827

Luxurious Ocho Rios Waterfront Villa: Private Pool, BBQ, Chef, Nr. Attractions

Tower Isle villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 16

“My stay here was heaven on earth.” My stay on this villa was great. Everything I could imagine and more Food was delicious and authentic; not process or frozen. The master suit where I stayed was immaculate. The power shower to the huge jacuzzi bath. The king size bed made my night rest wonderful. It's felt like I was sleeping on clouds. This villa was hard for me to leave, from pool, xbox, board games and a fantastic pool why must I go outside.(lol). When I decided to go outside it was also a great and wonderful experience. I visited duns river falls, when to the hot spot night club margarita ville, oceans 11, and amnesia. We sang karaoke had great Jamaica drinks and watch the beautiful scenery. All these great attraction only 12mins tops from the villa. However my highlight of the stay is the private beach, only 2min walk from the villa. Great vacation I'm booking another stay for January andirons can't wait...

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$976

Out of the Blue Villa

Treasure Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

1 of 3 filters match

Price per night from

$1,148

Sol Mar Villa

Silver Sands villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$505

Responds fast! avg. 54 minutes

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

1 of 3 filters match

Price per night from

$689

Beautiful Yellowbird Villa

Silver Sands villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

1 of 3 filters match

Price per night from

$482

3 BD VILLA INCLUDES HOUSEKEEPER/AIRPORT TRANSFERS

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Shared outdoor pool (heated), Private pool, Swing set or jungle gym

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Price per night from

$276

KINGSTON COTTAGE - Tropical Serenity - B&B

Kingston cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Exceptional service and amenities” Natalee and Barbara provided warm genuine hospitality during our stay. Breakfast was on time and exquisite every morning, a little Jamaican food, a little continental fare, your wish is their command. The facilities were clean, comfortable and the internet access fast. It was as if you were staying in a luxury resort. The hidden secret is the flora, if you like flowers, if you like orchids, you will be delighted in your stay. There are orchids of every color and type in the gardens which are a botanists dream.

1 of 3 match: Shared outdoor pool (heated), Private pool, Swing set or jungle gym

1 of 3 filters match

Price per night from

$104

Edgewater Beach Villa - Ocho Rios - Oceanfront Villa

Ocho Rios villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

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Price per night from

$1,125

2 Bedroom Apt, 6 Minutes away from Airport Montego Bay

Montego Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Looks exactly like the pics.” I would stay here every trip to Mo Bay!!! The owner met me at the airport on time, was friendly and offered a ride. Since I already had a ride we followed him to the property. If I was not with a local I would of got lost for it was several twist and turns before entering the locked gates of the property. Close drive to everything. The neighbors were friendly. As I entered the 3rd floor apartment it felt like home. Every room looks like the pictures posted. We were provided pots, utensils, plates, drinks (liquor), wifi, cable, stereo system, telephone, linens, basically everything as if you were home except for food. Ac is only in the master bedroom however there was a breeze during the day (please note I traveled in October when it is much cooler in Jamaica). The first day I took a cold shower but the rest of the days I had hot water. I like nice views and I could see the ocean from the living room. Thanks Ian!!!

Responds fast! avg. 3 hours 53 minutes

1 of 3 match: Shared outdoor pool (heated), Private pool, Swing set or jungle gym

1 of 3 filters match

Price per night from

$80

Tropical Dreams: Sunny, picturesque, Large and Beautiful Frontroom

Kingston private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful place to be!” We were looking for more of a cultural experience and this was a wonderful place to start! Vivienne and Lloyd are amazing and we so enjoyed the time we had with them. We are already planning another vacation and will definitely be staying here again when in Kingston!! Our new home away from home!! Thanks again Viv and Lloyd for such great hospitality!!!

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

1 of 3 filters match

Price per night from

$52

Allamanda - Montego Bay 5 Bedrooms

Montego Bay house

  • 5 bathrooms
  • sleeps 2

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

1 of 3 filters match

Price per night from

$1,718

Chill-in-Negril (NEGRILCONDO)

Negril apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 1 minutes

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

1 of 3 filters match

Price per night from

$98

Linga-Awile - Discovery Bay 3 Bedrooms

Discovery Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

1 of 3 filters match

Price per night from

$616

Luxurious 1 BdRm Ocean Front Condo in Montego Bay

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“WONDERFUL TIME!” Property is beautiful....This is my second stay at the Palmyra and once again we had a wonderful time. This is a condo that is built on the most beautiful beach there is in Montego Bay, between the former Ritz Carlton and Hilton Rosehall hotels. We had views of both beach and mountains. I can still feel the tradewinds. Sharon, the owner is most gracious and the staff there was very attentive and accomodating. Thank you all, So, Sharon Im ready to book my vacation for Feb, 2015. This time NO KIDS. Looking forward til Feb. Denise

Responds fast! avg. 3 hours 48 minutes

1 of 3 match: Private pool, Swing set or jungle gym, Shared outdoor pool (heated)

1 of 3 filters match

Price per night from

$224

Doubloon Villa, large pool and sandy beach at heart of Treasure Beach

Treasure Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Most amazing vacation and service I've ever had” There are so many wonderful things to say about this vacation its hard to consolidate it down :) The house is absolutely amazing. Each bedroom is special and unique and the outdoor living space is more than we could dream of. Hio and Nadine were our chefs and housekeepers and I couldn't say anything better about those two - they made the most delicious food, helped us with any favors or questions we had, and probably made too many trips to the grocery store (and liquor store!) than usual for us! Robert was awesome as the groundskeeper - as soon as it started raining (which probably lasted 5 minutes the entire trip) he would appear out of thin air to get the outdoor seat cushions out of the rain. We had such a great time and it was my husband and mine's first time bringing our friends - its a different kind of vacation, much more authentic and cultural than most are used to so we were a little nervous about how they would like it but everyone agreed - this vacation was amazing. I would highly recommend it to anyone looking for a more relaxing, private, and less touristy vacation spot.

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

1 of 3 filters match

Price per night from

$729

Tranquility Villa - Port Antonio & Blue Mountains

Port Antonio villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Fabulous, relaxing, beautiful, private...” This was my second time staying at Tranquility, (15th trip to Jamaica), My stays at Tranquility, were by far the best! Each stay gets better and better! I love the home, it's beautiful, spacious, clean, private, and the view is priceless! It's far enough away from everything, that you have the privacy you desire, but it's close enough to experience everything Jamaica has to offer. The food the cook made was fabulous, it was wonderful to have exactly what we wanted for our meals. (Helpful if your'e vegetarian, or have special dietary needs- one of us is vegetarian and the other, not). Can't pinpoint what I like most. Meals outside with a beautiful view and flower decorations on the table, lots of sun on both sides of the house, the food, swimming pool...? I loved, loved, loved everything! All of my vacation needs were met, and then some! Can't wait to get back!

1 of 3 match: Shared outdoor pool (heated), Swing set or jungle gym, Private pool

1 of 3 filters match

Price per night from

$345

Sea View Heights Villa Montego Bay

Rose Hall villa

  • 16 bedrooms
  • 16 bathrooms
  • sleeps 36

Responds fast! avg. 1 hour 29 minutes

1 of 3 match: Private pool, Swing set or jungle gym, Shared outdoor pool (heated)

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Price per night from

$287

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