Vacation Rentals & Houses in Jamaica

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Caribbean Sea Dreams, 2 bdroom with housekeeper/cook

Montego Bay townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 2 hours 0 minutes

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Cot available

1 of 3 filters match

Price per night from

$230

1 of 3 match: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$917

Fiwi Endz (Glenroys Guest Apt)

Ocho Rios apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Cot available

1 of 3 filters match

Price per night from

$63

TEST PROPERTY

Port Royal chalet

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 3 match: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$246

Villa by the Cove

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Cot available, Private outdoor pool (unheated), Climbing frame

1 of 3 filters match

Price per night from

$287

Village Maria~ A true Jamaican villa experience Beachfront

Montego Bay house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Cot available, 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: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$803

Calming Waters Riverside Villa & Yoga Retreat

Montego Bay villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Cot available, 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: Cot available, 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: Cot available, 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: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

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: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$230

Where the Cliffs and the Beaches Meet

Negril house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

“Home away From Home” This was a family trip. It was four adult women and 3 adult men. We stayed September 14-17 and had a wonderful time at Llantrissant. Ms. Anne, Ms. Paulette, Danny, Benjie, Charma and Barry were all very professional and very accommodating, by the time we left they felt like family. Ms. Anne and Ms. Paulette prepared excellent meals. The house was homey and we all felt right at home. It's an older house but very well kept along with the landscape and beach area. The veranda (which is were we spent most of our time while we were at the house) provided for an excellent view. We loved having the private beach area. Charma (and Barry) walked the yard at night and made us feel very safe. I was a little nervous because you really don't know what to expect when you're communicating through email and over the phone. But Craig and afua were patient with me and answered all of my questions and as soon as we got to Llantrissant the staff put us all at ease. They welcomed us with open arms. We look forward to returning in the future!!

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Cot available

1 of 3 filters match

Price per night from

$643

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: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

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: Cot available, 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: Cot available, 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: Cot available, 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

2 of 3 match: Private outdoor pool (unheated), Cot available, Climbing frame

2 of 3 filters match

Price per night from

$224

Sol Mar Villa

Silver Sands villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$505

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

Montego Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 3 match: Cot available, Private outdoor pool (unheated), Climbing frame

1 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: Cot available, Private outdoor pool (unheated), Climbing frame

1 of 3 filters match

Price per night from

$87

Private 2 bed Hill Top Villa to rent rural Jamaica

Santa Cruz villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Cot available

1 of 3 filters match

Price per night from

$65

Beautiful Yellowbird Villa

Silver Sands villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 3 match: Cot available, 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: Cot available, 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: Cot available, 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: Cot available, 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: Cot available, 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: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$1,718

Linga-Awile - Discovery Bay 3 Bedrooms

Discovery Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$616

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.

2 of 3 match: Climbing frame, Cot available, Private outdoor pool (unheated)

2 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: Cot available, 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: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$172

Sun & Sand Beach Condo with Wifi ( Sleeps 4 )

Ocho Rios apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Location yes! housekeeping staff no...” Hello, we just came back from a week in Ocho Rios and had a fantastic time. The condo we rented was not in the tower shown in the picture but in the adjacent hotel, which was good too. And yes, location in great. Right next to a nice beach with a pool in the complex. So, as I mentioned, location was great. However, housekeeping left to be desired. We were told that the condo would be cleaned every 2 days, but after 3 days, no one had come to bring fresh towels or toilet paper! We had to call and call to get some service. Also, when we asked for some dishwashing soap, we were told to use either hand soap or soap for clothes. So aside from the little hickups with the housekeeping staff, I would recommend this rental.

1 of 3 match: Cot available, Private outdoor pool (unheated), Climbing frame

1 of 3 filters match

Price per night from

$114

Lhorizon A Jewel in the Caribbean

Ocho Rios villa

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 22

“You Promised...You Delivered!” Our group of 18 (13 adults and 5 children) stayed at L’Horizon for a week in January 2015. The entire experience, from booking to the time of the stay, was amazing. The owner, Barrington, was more than helpful and very responsive during the planning phase. And then we arrived! We were greeted by the Manager and staff with smiles, “welcomes”, and rum punch. The house was immaculate and the rooms were very spacious and more than sufficient for our large group. The staff kept the house spotless the entire stay even with 5 young kids doing what they do best (making a mess). The first day, we were provided a cell phone to reach the Manager (Kelly) if there were any issues that needed to be addressed. The cell phone also gave us the opportunity to make local calls which came in handy. We had pre-arranged a formal family dinner (details worked out with Barrington) for the day after our arrival which turned out to be a huge success! The food was amazing and included everything we requested. Each night thereafter we had delicious dinners prepared by the cook (thank you Miss Rose!). We did not purchase the all-inclusive package so we had to purchase our own food which was a bit inconvenient. This was a lesson learned (not the owners fault) and we all agreed that next time, all-inclusive would be the way to go. Regardless, breakfast and dinners were tastily prepared to order. We mostly went out for lunch or brought lunch back to the house. This gave us a chance to go out and see what the area had to offer and try some local foods. We even tried the local KFC which we were told was much different from those in the US. We proved that was true . While we didn’t get an all-inclusive package, inclusive in our package was a personal driver who took us wherever we wanted to go locally. We had the opportunity to go shopping, eat at local seafood and jerk spots (yummy), visit the Dunn’s River Falls (a must-do), and our “party group” even got driven to local dance clubs and picked up at 2:30 and 3:30 in the morning! On the nights we stayed in, we hung out at the Jam Eng Bar on the property by the pool, danced, and sang! The bartender was amazing and tons of fun! As for the younger kids, they lived in the pool and had an amazing time. When they were not in the pool, the private beach was only a quick 5-minute walk away. But let’s not forget the older crowd. My mom, aunt, and mother-in-law spent their days relaxing poolside and around the house (so many places to relax) chatting it up with the staff that were all so very friendly. The entire family agreed that this was one of their best vacations ever! We’ve even talked about the next time we’ll vacation at L’Horizon. A special thank you to Barrington and his wonderful staff at L’Horizon for making this vacation one of the best my family has ever had! For us, you more than delivered on your promises!!

1 of 3 match: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$1,622

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!!!

1 of 3 match: Private outdoor pool (unheated), Climbing frame, Cot available

1 of 3 filters match

Price per night from

$459

Serendipity - Spring Farm, Montego Bay 6 Bedrooms

Montego Bay house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 1

1 of 3 match: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$1,583

Idleawile - Rio Bueno 6 Bedrooms - ask about our 3, 4 and 5 Bdrm rates

Discovery Bay house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

1 of 3 match: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$1,002

Malatai - Ocho Rios 6 Bedroom Beachfront - Ask about 4 & 8 bedroom Rates

Ocho Rios house

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 16

1 of 3 match: Cot available, Climbing frame, Private outdoor pool (unheated)

1 of 3 filters match

Price per night from

$4,294

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