Middleton Rentals

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257 Houses

Crowne Gardens Retreat

Middleton house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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$1,826

Millsborough B and B, Billy Dunn, Barbican, Liguanea, Kingston 6, Jamaica

Middleton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Great rentals within 20 miles that match your search

Modern Vacation Rental Awaits You

Portmore house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$103

Orchid View

Kingston apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$120

Cattleya's Executive Suite-Kingsway

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$92

Yard Style - Jamaica

Kingston house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$40

Coolahah Manor Portmore

Portmore house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$114

The Pentwood@Charlton

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$75

The Hugh Suite

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$80

Kozy Korner Comfy Bedroom

Kingston private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$52

Penny-wise/Pound-wise in Kingston!!

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$63

The Inn at 6

Kingston townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$457

Strathairn116

Kingston house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$96

Lovely 2 bedroom in Kingston City

Kingston apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$126

1 Bedroom Apt (Casa Pinto Guest Apartment) Kgn, JA

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 45

Responds fast! avg. 3 hours 54 minutes

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$91

Garden Oasis 3 bedroom Apt

Kingston apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$206

A spacious property awaits you!

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$80

Lofts at Lavant Apartment #7

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$114

Vacation Oasis 2 BR House Gated Community 4295143

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$103

Perfect location in New Kingston (Luxury Apartment)

Kingston apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$172

Beautiful & Convenient 1 Bedroom

Port Royal apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$75

The Havendale Vacation Haven

Kingston house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$75

Shotover Gardens Estate - cottage with pool

Port Antonio log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$57

2 Bedroom Luxury Apartment, (Casa Tianna Kingston)

Kingston apartment

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 54 minutes

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$132

1 Bedroom Luxury Apartment, (Casa Tianna Kingston)

Kingston apartment

  • 1 bedroom
  • 3 bathrooms
  • sleeps 2

“Very good” The accommodation was very good. Very Luxurious and safe.Being that it was my first time to Kingston I was naturally nervous about safety but Kevin went out of his way to make sure I felt very safe. I was picked up by a driver once I landed at the airport and taken straight to the beautiful accommodation. I will definitely be staying there every time I come to Jamaica

Responds fast! avg. 3 hours 54 minutes

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Price per night from

$79

Kensington Place Apartment @ New Kingston

Kingston apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Comfortable” Hi Had the privilege of staying 3 nights at this beautiful apartment. it felt safe, comfotable, and relaxing. not only will i be staying here in the future i will recommend it to any of my friends. also the professionalism of the staff was above and beyond. great choice

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$172

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!!!

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Price per night from

$105

Vacation rental Jamaica home away from home enjoy a quiet community

Spanish Town apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$92

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

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Price per night from

$86

Kingston Vacation Rental Call 1876-631-2910

Kingston cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“A WONDERFUL PLACE TO STAY....” MRS.Ragbeir, and family were most helpful. the place was clean and very welcoming. I will be planning many more trips here. any questions or any help getting around kingston just ask and Mrs.Ragbeir will be there to help you. The place is very quiet and very safe. I had no worries, thank you Mrs.Ragbeir for all your help... :-)

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Price per night from

$69

Kingsworth BnB

Kingston b&b

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 13

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Price per night from

$240

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.

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Price per night from

$103

1 BD / 1 BR Luxury Apartment

Kingston apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$103

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!!!

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$52

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!

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Price per night from

$343

Sea View Heights Villa Montego Bay

Rose Hall villa

  • 16 bedrooms
  • 16 bathrooms
  • sleeps 36

Responds fast! avg. 1 hour 29 minutes

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Price per night from

$286

Strathairn110

Kingston house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Sweet deal!” This vacation rental is cozy, comfortable, affordable, safe, and boasts a great location. I have stayed here on two separate occasions. Perfect place to stay!

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Price per night from

$96

Shotover Gardens Estate-Villa with Pool

Port Antonio villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Green paradise with great pool, great food, beautiful gardens.” This place was great! You're on top of a mountain so the views are breathtaking. The gardens are incredible with all kinds of edible fruits, neat birds and pretty flowers. Our family loved the pool, with a fully shaded wading pool for our little guy, plus the big pool and a hammock in the shade (only meters from the wading pool so you can relax while they splash). We were there with a big group and spent our nights in one of the smaller rooms in the villa, the luxurious master bedroom was incredible though (even has a beday!) The traditional Jamaican cuisine was fantastic! I would definitely recommend choosing the cook option because it's about a 20minute drive down a bumpy road to get to town, and it's really nice (and affordable) to just have the cooking and dishes all taken care of. The atmosphere was really relaxing. The smaller bedrooms were a little unfinished but the owner said he's going to be sprucing things up a little in the next couple months. He was great about fixing things we asked for (got a new toaster oven to replace an old one, fixed our squeaky bedroom door and got us a waste basket for our room when we asked). The snorkeling and river walk that he set up for us were fantastic. If you're looking for an authentic Jamaican experience this is the spot for you.

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Price per night from

$172

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