Portland Holiday Rentals

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Top Holiday Rentals Destinations 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 NZ$327
per night
13 May - 14 May
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
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 NZ$347
per night
13 May - 14 May
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 NZ$951
per night
13 May - 14 May
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 NZ$107
per night
13 May - 14 May
Cozy Cottage In Rural Jamaica. Rich In Sunshine, Colour, Flavour, And Warmth.
Executive Apartment, 1 King Bed, Kitchen | Living area
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 NZ$265
per night
14 May - 15 May
20 South Apartment
Deluxe Apartment, 1 King Bed, Terrace, Garden Area | Private kitchen
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
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 NZ$140
per night
20 May - 21 May
Abacus Jamaica the Zana Suite
Standard Studio Suite, Non Smoking | Private kitchen
Norwood Studio
3.0 star property
8.2 out of 10, Very good, (21)
"It was ok, all considering."
The price is NZ$274
per night
24 May - 25 May
Norwood Studio
Premium Apartment, 2 Bedrooms, Ocean View, Executive Level | Private kitchen
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 NZ$310
per night
13 May - 14 May
New Kingston Guest Apartments II
Deluxe Condo, 1 King Bed, Kitchen, City View | Living room
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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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as NZ$107 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Recent reviews in Portland
Expedia verified reviews

Inn The Town

Inn The Town

5/5 Excellent
"The Inn In Town is home away from home. The amenities were beyond amazing. The staff was always there to help with any situation that arises even the guys that work on the overnight. Everyone in the family enjoyed themselves even the kids. I will definitely book again every time I come to Portland."
A verified traveller stayed at Inn The Town
Posted 3 days ago
Inn The Town