Vacation Rentals & Houses in Jamaica

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1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$47

Scenic/Spacious two Bedrooms Apartment Rental

Priory apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$64

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: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$373

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: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$230

Honeycomb Villa, Silver Sands

Silver Sands villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$614

Villa Paola Jamaica

Port Antonio villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$86

Villa by the Cove

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Staffed property, Shared indoor pool, Climbing frame

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Price per night from

$287

Covenant Stay Guesthouse near Montego Bay & Ochi

Falmouth house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$92

Beautiful Waterfront Studio

Negril studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$138

Beautiful home for nature friends

Negril villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$184

cosy farm house

Duncans private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$127

Casa Bella Villa

Rose Hall villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$804

Standard Room, one king bed OR two Double beds

Negril house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$65

Nickel's Garden Villas

Montego Bay house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$117

Luxury Villas with Beautiful Ocean Views

Ocho Rios villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$896

3BD Villa Including Housekeeper/ Airport Transfers

St. Ann's Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Shared indoor pool, Climbing frame, Staffed property

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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: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$689

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: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$643

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: Climbing frame, Shared indoor pool, Staffed property

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: Climbing frame, Shared indoor pool, Staffed property

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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: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$976

Out of the Blue Villa

Treasure Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 3 match: Staffed property, Shared indoor pool, Climbing frame

1 of 3 filters match

Price per night from

$1,148

Chaudhry at Holiday House Montego Bay

Ironshore apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

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Price per night from

$207

Private Home on 2 Fruited Acres w/ Beautiful Views

Negril house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$92

Pimento Oasis, Ocho Rios, St. Ann, Jamaica

Ocho Rios house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Shared indoor pool, Climbing frame, Staffed property

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: Climbing frame, Shared indoor pool, Staffed property

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

2 of 3 match: Shared indoor pool, Climbing frame, Staffed property

2 of 3 filters match

Price per night from

$213

Responds fast! avg. 54 minutes

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$689

carib apartments mahogany beach ocho rios

Ocho Rios apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Staffed property, Shared indoor pool, Climbing frame

1 of 3 filters match

Price per night from

$87

Kingsworth BnB

Kingston b&b

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$241

3 BD VILLA INCLUDES HOUSEKEEPER/AIRPORT TRANSFERS

Priory villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Shared indoor pool, Climbing frame, Staffed property

2 of 3 filters match

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: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$104

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: Staffed property, Shared indoor pool, Climbing frame

1 of 3 filters match

Price per night from

$138

Secrets and Dreams Studio Suite at Strawberry Fields Together!, Jamaica

Robin's Bay cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$322

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: Climbing frame, Shared indoor pool, Staffed property

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: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$345

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: Staffed property, Shared indoor pool, Climbing frame

1 of 3 filters match

Price per night from

$114

Zimbali Culinary Retreats

Negril b&b

  • 7 bedrooms
  • 10 bathrooms
  • sleeps 16

1 of 3 match: Climbing frame, Shared indoor pool, Staffed property

1 of 3 filters match

Price per night from

$143

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