Vacation Rentals & Houses in Jamaica

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City Oasis

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$63

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, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

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, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$230

TWIN PALMS RETREAT - MONTEGO BAY JAMAICA

Montego Bay townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$413

Turtle Beach Towers Penthouse 3Bdr.

Ocho Rios apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$230

Perfectly Located Studio Apartment In Ocho Rios

Ocho Rios apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 59 minutes

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$75

Drax Hall - Coconut Walk

Ocho Rios house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$150

Apartment Treasure -Sandcastles Resort, Ocho Rios

Ocho Rios apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$230

Garden Oasis 3 bedroom Apt

Kingston apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$207

Beautiful Waterfront Studio

Negril studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$138

Luxury rental with pool

Duncans private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$146

Vacation Oasis 2 BR House Gated Community 4295143

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$104

The palm

Tower Isle apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$115

Villas Sur Mer (1-Bedroom)

Negril cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$474

Perfect location in New Kingston (Luxury Apartment)

Kingston apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$172

Tropical Vacation Villa, Ocho Rios

Ocho Rios house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$230

"El Gem"

Ocho Rios apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$184

Standard Room, one king bed OR two Double beds

Negril house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$65

Joy Estate 1

Falmouth house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$230

Beautiful 2 bed 2 1/2 bath vacation apartment

Ocho Rios apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$139

Shotover Gardens Estate - cottage with pool

Port Antonio log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 3 match: Climbing frame, Shared outdoor pool (unheated), Private outdoor pool (heated)

1 of 3 filters match

Price per night from

$58

3BD Villa Including Housekeeper/ Airport Transfers

St. Ann's Bay villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (heated), Climbing frame, Shared outdoor pool (unheated)

2 of 3 filters match

Price per night from

$207

Cozy Montego Bay Studio Apartment Jamaica

Montego Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Beautiful apartment - Can Not Wait to Come Back” Lovely stay! Really clean apartment great for 2. Store downstairs was so easy to get groceries to make lunch. Alyssa made it into a kingsize bed for us last minute, and she was great arranging a driver to drop us at the airport for our 9am flight. Very cool location, we woke up every morning and walked right across the street to the beach. (Theres a free local beach if you keep walking to the left, but Docs Cave was worth the 5 bucks) Best part is everything you need you can walk to. The building is old but the apartment made up for it- we saw a couple others with their doors open and we felt lucky to get an updated one. And we got beach towels provided. Cant wait to go back. Thanks alyssa

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$114

Beautiful Exotic Tropical Paradise - Townhouse in

Montego Bay villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Just wow!” Very pleasantly surprised with the modern conveniences and comfort of this home in paradise. The location was central and easy to find. This will definitely be the way to spend vacations as opposed to a resort. Very relaxing. Well taken care of grounds and pool. Highly recommend.

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$270

Out of the Blue Villa

Treasure Beach villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

2 of 3 match: Shared outdoor pool (unheated), Climbing frame, Private outdoor pool (heated)

2 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, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$207

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!!

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$332

STUNNING 2 bed 2 bath beach front condo..making your Caribbean dream a reality

Ocho Rios apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Great Condo, Great Location” First time we have rented a condo from an owner through FlipKey. Everything from reservation confirmation, payment etc was very smooth. When we arrived on site the outside of the Towers was disappointing, but very common in tropical climates. But all was overlooked when we walked into the suite. So very nice, clean, clean, clean. Lots of room for my husband and I, as well as a daughter. Close to the beach, restaurants, shopping and taxis. The suite had everything you need. Reliable internet, fully equipped kitchen, tv in living room and master bedroom. Millicent met us on arrival and showed us around the suite as well as explained beach access etc. We had a great vacation and would definitely recommend this location. I was also impressed when the owner , Kenita came to say goodbye when we left. It was a pleasure to meet her. We hope to be back one day.

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$144

“Great place to stay!” I stayed here with my boyfriend this past week and we really enjoyed Point Village and the studio Domingos rented to us! The studio itself has a working stove, fridge, tv, air conditioner, and fan (plus wifi if you ask). Point Village is great because it is at the start of the 7 mile beach and is on private property so you will not be bothered on the beach, or anywhere else. It is quieter than what I saw of the rest of 7 mile beach and certainly more secluded. You can easily walk down the beach to a number of restaurants or bars or hop in a taxi to take to the west end. Personally, I loved it because it felt more like a community and home than any of the hotels we could have stayed at. Domingos was also a very gracious host who was always available and very willing to provide help and advice, or a drink! Nevertheless, it is a used-to-be resort that went bankrupt a couple of years ago so some parts of it are not that well maintained. If you are the type of person who loves or needs to stay at an all-inclusive resort this may not be the best fit for you. Another thing to keep in mind is it is next door to hedonism (a resort for mostly middle-aged nudes) and so on some parts of the property you can hear their music playing late at night (but for the most part it is very quiet). Regardless, I would certainly stay here, or in any of the other apartments in Point Village, the next time I visit.

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$127

Bruce Seacastles Vacation Penthouse

Montego Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“awesome” arrived at seacastle with a few friends for a girls weekend. The condo was nice,clean and very spacious. Everything was ready when we got there and the owner very courteous and even helped us with an extra night when we missed our flight.the hotel next door had a great bar and we enjoyed our stay very much. I would definitely recommend seacastle for a great relaxation trip

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$194

Pimento Oasis, Ocho Rios, St. Ann, Jamaica

Ocho Rios house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (heated), Climbing frame, Shared outdoor pool (unheated)

2 of 3 filters match

Price per night from

$224

1 Bedroom Condo in Bloody Bay Negril, Jamaica

Negril apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Heaven on EARTH!!!!” After reading numerous reviews I went into this rental with a very open mind especially after such positive interactions with the owners Kevin & Lisa. They communicated effectively regarding any and all transactions, support while staying there, as well as overall feedback needed at any timeframe. Upon arrival Dale was awesome as well as security which was above and beyond and helpful. The property itself left me speechless. There are updates throughout and I never felt that I lacked anything that any resort had to offer ; in fact there were more amenities; i.e. washer/dryer, surplus of dishes, numerous satellite channels, SONY IPOD, overall comfortable home setting. The residential area was quiet, peaceful and the beach amazing. The condo was stocked with more than enough linens & towels and I have never felt so much at "home" away from "home". Cabs are plentiful and it is about a 5-10 minute to town etc. but if you truly want to relax, avoid the busy day/nightlife escape to this rental and then venture out for the above. You have my word you will NOT be disappointed. I am definitely looking into renting again and I will also post pictures as well as video on my YouTube page: C Dioume

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$132

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: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$106

Villaggio Del Sol

Ocho Rios apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$373

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: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$86

Hill Top Kingston Jamaica

Kingston b&b

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

“Awesome place” I went to Hill Top with my Family last year and it was awesome, the staff were so nice to my kids, the place was clean and nice. The view there was spectacular, especially in the nights.

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$114

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 (heated), Climbing frame, Shared outdoor pool (unheated)

2 of 3 filters match

Price per night from

$213

High View Villa

Montego Bay villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 3 match: Climbing frame, Private outdoor pool (heated), Shared outdoor pool (unheated)

1 of 3 filters match

Price per night from

$689

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