Vacation Rentals in Portland

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Top Vacation Rentals in Portland

Property grounds
A place in paradise - family villa on a peninsula directly by the sea
10.0 out of 10, Exceptional, (48)
"We stayed at the Villa for our wedding in Port Antonio. Centrally located to the town centre. Very secluded and quiet with plenty of space so unlike a hotel you do not feel enclosed."
A place in paradise - family villa on a peninsula directly by the sea
Property grounds
Heaven Villa - We are not on the water, we are above!
10.0 out of 10, Exceptional, (7)
"Heaven Villa lived up to its name, with one of the best ocean views on the island from the infinity pool and the entire back of the place. We enjoyed ourselves to the fullest at Heaven, including spectacular authentic Jamaican meals prepared by the chef for breakfast and dinner, which we enjoyed as a group. The entire staff were topnotch, especially Marjorie who managed the operation and accommodated our every request. We all love her and will forever appreciate her lovely personality and...
Heaven Villa - We are not on the water, we are above!
Free WiFi
Reggae Legends Estate
2.5 star property
10.0 out of 10, Exceptional, (1)
The price is ¥26,498
per night
May 15 - May 16
Reggae Legends Estate
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Exterior
5 Star Fresh And Clean Condo In New Kingston
3.0 star property
10.0 out of 10, Exceptional, (4)
"I absolutely loved staying here,7 I will definitely be staying here the next time that I am visiting Kingston "
5 Star Fresh And Clean Condo In New Kingston
Private kitchen
NewKgn Gem
9.8 out of 10, Exceptional, (18)
"Clean spacious and met our needs. Reasonable priced and close proximity to business district and restaurants. Awesome stay!"
NewKgn Gem
Pool
Beautiful House, Sea and mountain View property less than 1 mile from shopping
9.6 out of 10, Exceptional, (5)
"First I must say this house is even more beautiful than the pictures. My Family and I loved , did I say loved this place. It deserves more than a 5 star ratings, it has everything I needed felt like I was at my own house. The property was CLEAN and exactly as described. The neighborhood was quiet and I felt safe. Everything I needed was in close proximity our host Mr. Anthony is amazing very understanding, readily available and accommodating. I am really looking forward to staying at this...
Beautiful House, Sea and mountain View property less than 1 mile from shopping
2 bedrooms, Egyptian cotton sheets, premium bedding, in-room safe
Casa Royale Guest Apartment
3.5 star property
9.6 out of 10, Exceptional, (67)
"Place was very clean and comfortable."
Casa Royale Guest Apartment
Outdoor pool
The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed
9.6 out of 10, Exceptional, (15)
"The house was very spacious and comfortable. The best view overlooking the mountains and ocean! The star of the entire stay was Chef Shane! Unbelievably the best variety and robust flavors in all he cooked for us! We all were so impressed with his presentation of food. He clearly cooks from his heart because you can taste the goodness in every spoonful! If it was not for Shane, Melissa and Antoinette this trip would not have been so memorable! I want to personally Thanks all 3."
The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed
View from property
Cozy Cabin in the Sky-Wood Thorpe Villa-Ocean View
9.2 out of 10, Wonderful, (10)
"We enjoyed our stay at Donnaa house very much. The view as well as the house is incredible. The kitchen offers all you need and the rooms are spacous and airy. My friend was ill but Donna helped us quick and was always here when we needed something. The only hard thing was the last bit of the road which is very steep. We had a little 4x2 car and made it up bit next time we would defenitely follow Donnas advice and rent a 4x4. However, we where very happy and if you want to stay in one of the...
Cozy Cabin in the Sky-Wood Thorpe Villa-Ocean View
Pool | Outdoor pool
Gated Luxury New Kingston 1 Bdrm Condo Pool & Gym
9.2 out of 10, Wonderful, (5)
"Safe complex and great location for lots of activities and good restaurants"
The price is ¥17,759
per night
May 19 - May 20
Gated Luxury New Kingston 1 Bdrm Condo Pool & Gym
Property grounds
Affordable Way to Wake Up to a Magical Sunrise from our Beach Front Villa
9.0 out of 10, Wonderful, (12)
"What a wonderful place! The people, the view, the food, all of it! You will not be disappointed!"
The price is ¥66,674
per night
May 14 - May 15
Affordable Way to Wake Up to a Magical Sunrise from our Beach Front Villa
Private kitchen
Harloe's Luxury Condominium
9.0 out of 10, Wonderful, (20)
"This property is in a great location great access to new Kingston and half way tree. I highly recommend this property it is well maintained nice and clean. If you have a clean and comfortable home then you can call this property a home away from home."
Harloe's Luxury Condominium
Beach nearby
Cozy Cottage In Rural Jamaica. Rich In Sunshine, Colour, Flavour, And Warmth.
9.0 out of 10, Wonderful, (11)
"It was a hidden gem staying at Tony’s! Norval offers very fair rates and Gary is always there to ensure that you’re well taken care of. Have to mention the ital sip from Gary is delicious!!"
The price is ¥5,241
per night
May 14 - May 15
Cozy Cottage In Rural Jamaica. Rich In Sunshine, Colour, Flavour, And Warmth.
Executive Apartment, 1 King Bed, Kitchen | Living area | Flat-screen TV
Cattleya's New Kingston Guest Apartment
3.5 star property
9.0 out of 10, Wonderful, (42)
"My only problem with this property is the parking situation! If you have a car make sure they guarantee you a parking spot before you book! I was given a number but they had a car in that spot the whole time I was there, this make my stay very inconvenient. I was woke up in the night by security to move my car because the owner park in spot am supposed to use or whoever that let use the parking space. Don’t advertise parking if you can’t accommodate it "
Cattleya's New Kingston Guest Apartment
Property grounds
20 South Apartment
3.5 star property
8.8 out of 10, Excellent, (5)
"It's was walkable, secure but the dish wasn't clean and the toilet seat was screwed down and filty "
The price is ¥17,561
per night
May 14 - May 15
20 South Apartment
Deluxe Apartment, 1 King Bed, Terrace, Garden Area | Private kitchen | Full-size fridge, microwave, oven, stovetop
New Kingston's Deluxe Apartment
3.5 star property
8.6 out of 10, Excellent, (32)
"I had a great experience here, very quiet I’m peaceful space to be in. "
New Kingston's Deluxe Apartment
Deluxe Studio Suite, 1 King Bed, Refrigerator & Microwave, Mountain View | 1 bedroom, premium bedding, in-room safe, individually decorated
Abacus Jamaica the Zana Suite
3.0 star property
8.2 out of 10, Very Good, (48)
"Always a safe and reliable spot to stay while in Kgn"
The price is ¥11,297
per night
May 20 - May 21
Abacus Jamaica the Zana Suite
Standard Studio Suite, Non Smoking | Private kitchen | Fridge, microwave, oven, stovetop
Norwood Studio
3.0 star property
8.2 out of 10, Very Good, (21)
"It was ok, all considering."
The price is ¥10,305
per night
May 24 - May 25
Norwood Studio
Premium Apartment, 2 Bedrooms, Ocean View, Executive Level | Private kitchen | Full-size fridge, microwave, oven, stovetop
New Kingston Guest Apartments II
3.5 star property
8.2 out of 10, Very Good, (22)
"I arrived an hour early for check-in. The front desk attendant informed me that they had never received my reservation from expedia. The attendant then called the apartment owner. The owner called me and also said that he had never received expedia reservation, but somehow he had my information; name check-in/out date etc. He informed me that he did not have a room on this property for me. He then wanted to move me to a property across town. I didn't want to be across town, because i had chosen...
The price is ¥23,942
per night
May 14 - May 15
New Kingston Guest Apartments II
Deluxe Condo, 1 King Bed, Kitchen, City View | Living room | Flat-screen TV
Kingston Luxury Condo Apartment
3.5 star property
8.0 out of 10, Very Good, (26)
"Very pleasant stay"
Kingston Luxury Condo Apartment
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Vacation Apartments in Portland

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