Vacation Rentals & Houses in Jamaica

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TWIN PALMS RETREAT - MONTEGO BAY JAMAICA

Montego Bay townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Children's pool

1 of 3 filters match

Price per night from

$413

1 of 3 match: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$917

TEST PROPERTY

Port Royal chalet

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 3 match: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$246

Drax Hall - Coconut Walk

Ocho Rios house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Children's pool

1 of 3 filters match

Price per night from

$150

Villa by the Cove

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Children's pool, Private outdoor pool (unheated), Climbing frame

1 of 3 filters match

Price per night from

$287

Coolshade Villa - Richmond - Ocho Rios

Ocho Rios villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Children's pool

1 of 3 filters match

Price per night from

$207

Vacation Oasis 2 BR House Gated Community 4295143

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Children's pool

1 of 3 filters match

Price per night from

$104

Village Maria~ A true Jamaican villa experience Beachfront

Montego Bay house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$861

Casa Bella Villa

Rose Hall villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$803

The Havendale Vacation Haven

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Children's pool

1 of 3 filters match

Price per night from

$75

Calming Waters Riverside Villa & Yoga Retreat

Montego Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$201

Luxury Villas with Beautiful Ocean Views

Ocho Rios villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$895

3BD Villa Including Housekeeper/ Airport Transfers

St. Ann's Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Children's pool, Private outdoor pool (unheated), Climbing frame

1 of 3 filters match

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: Children's pool, Climbing frame, Private outdoor pool (unheated)

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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: Children's pool, Climbing frame, Private outdoor pool (unheated)

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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: Children's pool, Climbing frame, Private outdoor pool (unheated)

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Price per night from

$2,004

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: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$826

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: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$975

Out of the Blue Villa

Treasure Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Children's pool, Private outdoor pool (unheated), Climbing frame

1 of 3 filters match

Price per night from

$1,148

Pimento Oasis, Ocho Rios, St. Ann, Jamaica

Ocho Rios house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Children's pool, Private outdoor pool (unheated), Climbing frame

1 of 3 filters match

Price per night from

$224

Signature's 21 @ the Country Club

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“beautiful escape” My friend and I recently stayed here and we loved it. The owner bancroft is very friendly and goes out of his way to accommodate his guest. He emailed me with the latest updates about the place and had a very helpful security guard. The security guard was also helpful with giving us directions to get around Jamaica. I absolutely recommend tho place, the view is spectacular. The stairs to the place is a little steer but just be careful. I'll definitely stay here again!!!

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Children's pool

1 of 3 filters match

Price per night from

$106

Chill on the hill..free wi fi

Ocho Rios apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

“LOOK NO FURTHER” Do not look any further! This is the place to be! The Biggs brothers will take really good care of you, and make sure every single need is met. The condo is gigantic, has two floors, 2 1/2 bathrooms, a gazebo patio off the living room, and a HUGE open terrace, on the 2nd floor. Both ensuite bedrooms are on that second level. The upper deck, has a clear view of the Caribbean sea, table and chairs, and pads to sit on. Please bring them inside when you are done, so they stay nice, for others. Its a massive condo, and has a very well stocked kitchen. We cooked dinner twice, but we sure enjoyed our morning Blue mountain coffee, every morning, taking in these VIEWS! WI-FI worked perfectly, there is cable TV for evenings in, and even better, the sound system tunes into IRIE-FM or any station you choose. Harry came to fix a lock and bring us s brand new coffee pot, and he did it immediately! They will not "drag their feet, like other renters. Phillip & Harry were both there to greet us, and help carry in our bags and groceries. The tour was efficient and thorough. The bureau's for your clothes is gorgeous cedar as is the headboard on the bed. There is ample closet space in both bathroom areas, to hang dresses or clothes you do not want wrinkled. Yes, they have an ironing board too, in case that happens. The view is fantastic, and one day, a cruise ship came in, and we had front row seats. June has less cruise ships, so that is the time, to experience DUNNS RIVER FALLS, and enjoy it with 20 people, as opposed to hundreds of people. Traveling "off season", has its perks! There are (5) pools around this rambling complex, of gardens and steps. We used the one closest to the condo, a few times. If you have any issue with the pool, call the number on the sheet they leave, and literally, in (5) minutes, someone will be there. Our son, age 20 was traveling with my husband and I. Trip Advisor does not have a "drop-down", to click traveling with FAMILY. The stairs could be a challenge for wheel chairs, but other than that, the walk is doable. We are NEVER going to rent from anyone else, and neither should you. Harry came back (2) days before we left, to return our security deposit, so there is no issue with that. We are very neat and clean, so we swept and mopped, and took out the garbage, put every dish away. Its called RESPECT, and since we got it from these brothers, we returned the vibe. We also made sure to "pay it forward", and leave toilet paper, and garbage bags, for the next LUCKY RENTER! I am telling you, LOOK NO FURTHER. Even if you read negative reviews in other condos in this complex, you will NOT have any issues, with APARTMENT 2-A in PHASE 4. We rented a car, so we covered the entire North Coast, and visited many beaches. If you have a vehicle, I am going to recommend that you have to go to SUGAR POT BEACH. Its a secret place, down a dirt road, behind Rio Nuevo gas station. "off the beaten path", is where you find the best places. This is one of them. When you follow this dirt road to the sea, the beach is spectacular, private, has shady parking, and the bar area, is made of stone and drift wood. The restaurant is adorable and they have many choices of island delights! The food is to die for. I ate curry conch two days in a row, and it was the best I ever had! I have eaten it in every parish on this island, over 29 years. The curry goat was also fresh and very seasoned. I want to take this time to thank Phillip, Clayton & Harry Biggs. They were the nicest, most responsible, caring renters, we have ever come upon. We loved their vibes, and honest to God, you will too! They work together, and call the condo phone, to make sure, everything is going well. They REALLY want your trip to leave you feeling IRIE. Best 16 days in JAMAICA, ever! THANK YOU FROM THE BOTTOM OF OUR IRIE HEARTS, and see you next time, for sure!

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Children's pool

1 of 3 filters match

Price per night from

$114

Sol Mar Villa

Silver Sands villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$505

Morgan's Retreat 2 BR House Gated Community near KGN and Portmore

Portmore house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 19 minutes

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Children's pool

1 of 3 filters match

Price per night from

$86

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

Montego Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Private outdoor pool (unheated), Children's pool, Climbing frame

2 of 3 filters match

Price per night from

$213

carib apartments mahogany beach ocho rios

Ocho Rios apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Children's pool, Private outdoor pool (unheated), Climbing frame

1 of 3 filters match

Price per night from

$87

Beautiful Yellowbird Villa

Silver Sands villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 3 match: Children's pool, Climbing frame, Private outdoor pool (unheated)

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: Children's pool, Private outdoor pool (unheated), Climbing frame

1 of 3 filters match

Price per night from

$276

Edgewater Beach Villa - Ocho Rios - Oceanfront Villa

Ocho Rios villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$1,125

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

1 of 3 match: Children's pool, Private outdoor pool (unheated), Climbing frame

1 of 3 filters match

Price per night from

$138

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: Children's pool, Climbing frame, Private outdoor pool (unheated)

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: Children's pool, Climbing frame, Private outdoor pool (unheated)

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: Children's pool, Climbing frame, Private outdoor pool (unheated)

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: Children's pool, Climbing frame, Private outdoor pool (unheated)

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 outdoor pool (unheated), Climbing frame, Children's pool

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: Children's pool, Climbing frame, Private outdoor pool (unheated)

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: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$345

Bogue Villa

Montego Bay villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“R & R at it's Finest!” I have stayed at this Villa three years in a row and am planning on going again for 2 weeks in February 2015! It is relaxing, comfortable and spacious and the staff are amazing as Sophia is the best and will make your stay incredible. I can't wait to return for my 4th visit!

Responds fast! avg. 3 hours 54 minutes

1 of 3 match: Children's pool, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$172

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