Vacation Rentals in Portland

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Top Cities in Portland

Winnifred Beach which includes general coastal views as well as a small group of people
Vacation RentalsVacation Rentals

Port Antonio

Port Antonio

Top Vacation Rentals 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.
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
Deluxe Studio Suite, 1 King Bed, Refrigerator & Microwave, Mountain View | 1 bedroom, premium bedding, in-room safe, individually decorated
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
$95 nightly
The price is $96
Nov 19 - Nov 20
Total with taxes and fees
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
$269 nightly
The price is $310
Nov 19 - Nov 20
Total with taxes and fees
Reggae Legends Estate
Deluxe Apartment, 1 King Bed, Terrace, Garden Area | Private kitchen | Full-size fridge, microwave, oven, stovetop
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)
"We had a great stay. Apartment was clean and comfortable.."
United States
Barbara C.
Exquisite, recently renovated studio apartment
Superior Apartment, 1 Bedroom, Ensuite | 1 bedroom, Egyptian cotton sheets, in-room safe, individually decorated
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
$175 nightly
The price is $272
Nov 14 - Nov 15
Total with taxes and fees
Kingsway New Kingston Guest Apartment II
Executive Apartment, 2 Bedrooms, Kitchen | 2 bedrooms, Egyptian cotton sheets, in-room safe, individually decorated
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
$65 nightly
The price is $208
Nov 19 - Nov 20
Total with taxes and fees
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
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
$136 nightly
The price is $268
Nov 19 - Nov 20
Total with taxes and fees
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
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
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 traveler
$124 nightly
The price is $224
Nov 6 - Nov 7
Total with taxes and fees
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

R Hotel Kingston

R Hotel Kingston

10/10 Excellent
"The staff are exceptionally helpful, accommodating and friendly. "
RENAE L 3-night trip
Posted 3 days ago
R Hotel Kingston

Find out more about Portland

Discover your perfect Portland vacation rental with Expedia

How many vacation rentals are available in Portland?


Expedia has plenty of vacation rentals to choose from in and around  Portland, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Portland?


The selection of Portland vacation rentals we have selected for you start as low as $96 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Portland?


Vacation rentals in Portland come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Portland vacation rentals to suit everyone. 


Why should I choose a vacation rental in Portland?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Portland vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Portland?


Find vacation rentals in Portland by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Portland.  


What amenities are available in a vacation rental in Portland?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Portland vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Portland?   


Everytime is a great time to head to Portland! Staying in a Portland vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Portland. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Portland vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Portland, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Portland vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.