Portland Holiday Rentals

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Top Holiday Rentals Destinations in Portland

Outdoor pool
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
9.0 out of 10, Wonderful, (10)
"The home is so beautiful and well kept. There were 10 of us that stayed in Spicy Hill and it still felt like plenty of space. The pool and garden is beautiful and there’s a great games room. The property is also perfectly located as you can walk to Frenchman’s Cove and the Blue Lagoon. We rented a car from Kingston which i’d recommend so we could drive the 10minutes from the house into town. What made the stay so special was the 3 wonderful caretakers who were incredibly helpful, welcoming and...
United States
Nathan A.
The price is NZ$1,742
includes taxes & fees
24 Nov - 25 Nov
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
Deluxe Studio Suite, 1 King Bed, Refrigerator & Microwave, Mountain View
Abacus Jamaica the Zana Suite
Abacus Jamaica the Zana Suite
3.0 star property
8.2 out of 10, Very good, (57)
"Very nice hostess, attentive and helpful. Loveliette is a lovely and helpful woman."
United Kingdom
Kazeem
Abacus Jamaica the Zana Suite
Terrace/patio
The Gardens
The Gardens
3.0 star property
7.4 out of 10, Good, (53)
"I really enjoyed my stay here,the property was VERY clean,the pool was VERY clean,the view from my room was excellent,omg the bed was very comfortable,this place just gave me a peace of mind,and the owner Anika I give her a huge thumbs up,she was very friendly and helpful it was a 10/10 experience for me.."
United States
Sonika
The price is NZ$178
includes taxes & fees
14 Nov - 15 Nov
The Gardens
Exterior detail
Harloe's Luxury Condominium
Harloe's Luxury Condominium
8.2 out of 10, Very good, (34)
"I iked everything about the property. It was clean, quiet, beautiful and I felt safe. The security was respectful and professional. It's a very nice place, very convenient because it is in a nice area, close to everything. I would rent it again."
Canada
eugene
Harloe's Luxury Condominium
1 bedroom, free WiFi
Reggae Legends Estate
Reggae Legends Estate
2.5 star property
9.6 out of 10, Exceptional, (5)
"After a handful of stays here, this definitely feels like a home away from home. If you're looking for a traditional hotel experience with typical hotel amenities, this may not be the spt for you (although it still may be - they have god wifi, TVs, a proper full kitchen, a pool and an onsite restaurant), but I will stay here every time I visit the Kingston area due to the good energy, friendly communication, beautiful property and location, the yummy breakfast - and the proximity to the things I...
United States
Kathleen
The price is NZ$609
includes taxes & fees
7 Nov - 8 Nov
Reggae Legends Estate
Deluxe Apartment, 1 King Bed, Terrace, Garden Area | Private kitchen
New Kingston's Deluxe Apartment
New Kingston's Deluxe Apartment
3.5 star property
8.6 out of 10, Excellent, (55)
"Great stay"
United States
Michelle
New Kingston's Deluxe Apartment
Outdoor pool
New Kingston Guest Apartments at Abbey
New Kingston Guest Apartments at Abbey
3.5 star property
8.8 out of 10, Excellent, (21)
"No one was available to check us in and no email was sent with instructions. The apartment looks ran down but on the picture it looks completely different. I was charged the rate and no yet was money refunded. Terrible service "
United States
Shereeta
New Kingston Guest Apartments at Abbey
Fridge, microwave, stovetop, electric kettle
Exquisite, recently renovated studio apartment
Exquisite, recently renovated studio apartment
9.6 out of 10, Exceptional, (20)
"The room was as expected, clean and well equipped."
United States
Brian oliver
Exquisite, recently renovated studio apartment
Superior Apartment, 1 Bedroom, Ensuite
Kingsway New Kingston Guest Apartment II
Kingsway New Kingston Guest Apartment II
3.5 star property
9.8 out of 10, Exceptional, (18)
"This was the first time I ever booked a place so I was pretty hesitant going in. But staying here has helped alleviate my fears. Awesome place"
United States
Akeem
The price is NZ$468
includes taxes & fees
14 Nov - 15 Nov
Kingsway New Kingston Guest Apartment II
Executive Apartment, 2 Bedrooms, Kitchen
New Kingston Corporate Apts at Donhead
New Kingston Corporate Apts at Donhead
3.5 star property
9.6 out of 10, Exceptional, (31)
"Wow, we rented this accommodations for Jamaica carnival and was very lucky. It was 5 minutes away from the Bob Marley Museum. 10 minutes from Devon house, the best ice-cream in Jamaica. It was very centrally located where we weren't far from anything. The unit itself is spotless and clean. It was a very well kept unit. QUICK callout to please call them 72 hours in advance to give them the heads up that you're checking in. That was the only quirky step. The unit also had a washer and dryer. "
United States
Kenisha
New Kingston Corporate Apts at Donhead
Exterior
Stylish Studio in Chelsea Manor
Stylish Studio in Chelsea Manor
2.0 star property
10.0 out of 10, Exceptional, (1)
"I loved that it was private and the staff was very welcoming everything was exactly what i wanted. I definitely would book agsin everything was so clean and neat"
United States
DONNA
The price is NZ$368
includes taxes & fees
7 Nov - 8 Nov
Stylish Studio in Chelsea Manor
Outdoor pool
Tapioca Village Retreat
Tapioca Village Retreat
3.0 star property
6.0 out of 10, (2)
"Was so turned off by the cockroaches and the pool extremely dirty that I couldn’t eat the breakfast provided. Place is not yet finished. Bad experience "
United States
Lavern
The price is NZ$164
includes taxes & fees
13 Nov - 14 Nov
Tapioca Village Retreat
Apartment | Interior
Loft - Sleeps 4 - Parking - Balcony
Loft - Sleeps 4 - Parking - Balcony
3.0 star property
7.4 out of 10, Good, (6)
"Excellent location,easy access to food, entertainment and airport. Apartment was clean and cozy. The only thing we missed was having hot water ."
United States
Tiania
Loft - Sleeps 4 - Parking - Balcony
Property entrance
CTBH at EI8HT Super Studios
CTBH at EI8HT Super Studios
3.0 star property
8.0 out of 10, Very good, (2)
"Great Location, accessible to everything, clean, safe, environment. Close to restaurants, shopping and attractions. Excellent communication with property manager. Sweet delicious mangos from the trees on site. "
United States
Beverley
CTBH at EI8HT Super Studios
Exterior
The Artist Place @ Kensington New Kingston
The Artist Place @ Kensington New Kingston
9.0 out of 10, Wonderful, (8)
"It was a great stay. I am usuall a major hotel chain user and ventured into this time of accommodations for the first time and it was a success. Thanks to the owner for all the help and support she providing in making my stay great..."
United States
Emanuel G.
The Artist Place @ Kensington New Kingston
Front of property
Casa Alexandria Guest Apartment
Casa Alexandria Guest Apartment
3.5 star property
9.6 out of 10, Exceptional, (56)
"Booked this room a few hours before we came. Called the number to confirm our arrival. No one answered the phone. Texted and called on their regular phone as well as WhatsApp - no replies. It’s showing left on read. No response. Drove to the address - the neighborhood is a scary and absolutely not safe. Kept on calling them and knocking on a locked gate - no luck. Waited there for an hour. No one showed up or answered the phone. Tried getting a refund - they said “the policy is that you have to...
United States
Aleksandr
The price is NZ$442
includes taxes & fees
8 Nov - 9 Nov
Casa Alexandria Guest Apartment
Exterior
New Kingston Serenity at The Oxford
New Kingston Serenity at The Oxford
8.8 out of 10, Excellent, (15)
"It was clean and the location was accessible "
United States
Damian
New Kingston Serenity at The Oxford
50-inch LED TV with cable channels, Netflix, streaming services
Sweet Kensville
Sweet Kensville
4.0 star property
9.4 out of 10, Exceptional, (3)
"Great stay"
United States
Steve
The price is NZ$418
includes taxes & fees
7 Nov - 8 Nov
Sweet Kensville
Exterior detail
COMFORTABLE APARTMENT WITH BEDROOM, LIVING ROOM, KITCHEN
COMFORTABLE APARTMENT WITH BEDROOM, LIVING ROOM, KITCHEN
7.6 out of 10, Good, (7)
"It’s like being home away from home. I would book to stay here again. "
United States
Everol
The price is NZ$141
includes taxes & fees
15 Nov - 16 Nov
COMFORTABLE APARTMENT WITH BEDROOM, LIVING ROOM, KITCHEN
Outdoor pool
New Kingston Guest Apartments at Seymour
New Kingston Guest Apartments at Seymour
3.5 star property
8.8 out of 10, Excellent, (6)
"Enjoyed my stay here at this apartment, it was perfect for my little trip. Sheldon is a great property manager. Thanks again for everything."
United States
Anonymous traveller
The price is NZ$396
includes taxes & fees
9 Nov - 10 Nov
New Kingston Guest Apartments at Seymour
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.
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Top Portland Hotel Reviews

S Hotel Kingston

S Hotel Kingston

10/10 Excellent
"Spotless room and courteous staff"
GEORGE 2-night trip
Posted 21 hours ago
S Hotel Kingston

Find out more about Portland

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$141 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.