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 dining
Rose Hill Villa with sea view

Rose Hill Villa with sea view

Port Antonio
Rose Hill Villa with sea view
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
Constant Spring
8.2 out of 10, Very Good, (59)
"Great spot for a quiet stay, staff was extremely helpful."
United States
Hopeton
$95 nightly
The price is $106
Nov 13 - Nov 14
Total with taxes and fees
Abacus Jamaica the Zana Suite
Terrace/patio
The Gardens

The Gardens

3.0 star property
Barbican
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 13 - Nov 14
Total with taxes and fees
The Gardens
1 bedroom, free WiFi
Reggae Legends Estate

Reggae Legends Estate

2.5 star property
Jack's Hill
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 15 - Nov 16
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
Half Way Tree
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
New Kingston
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
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
Half Way Tree
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
$275 nightly
The price is $293
Nov 20 - Nov 21
Total with taxes and fees
Kingsway New Kingston Guest Apartment II
Exterior
Stylish Studio in Chelsea Manor

Stylish Studio in Chelsea Manor

2.0 star property
New Kingston
8.0 out of 10, Very Good, (2)
"The staff greeted me warmly and were incredibly friendly throughout my stay. While the amenities were limited and the decor a bit outdated, I appreciated how clean and presentable the apartment was during my short visit. With a few modern updates and some repairs, this place could truly shine and provide an even more enjoyable experience. "
United States
Ritania
$202 nightly
The price is $233
Nov 16 - Nov 17
Total with taxes and fees
Stylish Studio in Chelsea Manor
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
New Kingston
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
The Artist Place @ Kensington New Kingston

The Artist Place @ Kensington New Kingston

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
Outdoor pool
Tapioca Village Retreat

Tapioca Village Retreat

3.0 star property
Castleton
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
$80 nightly
The price is $93
Nov 13 - Nov 14
Total with taxes and fees
Tapioca Village Retreat
Superior Apartment, 2 Bedrooms, Terrace, Courtyard View | Terrace/patio
Skyview Manor Guest Apartments

Skyview Manor Guest Apartments

3.5 star property
Jack's Hill
8.4 out of 10, Very Good, (16)
"Property needed 72 hour notice to book. Expedia didn't honor that rule. They booked me the same day so i wasnbable to stay. I was stranded from 6pm-11pm. Ended up cancelling the whole trip and returning home!"
United States
Shirlene
Skyview Manor Guest Apartments
Apartment | Interior
Loft - Sleeps 4 - Parking - Balcony

Loft - Sleeps 4 - Parking - Balcony

3.0 star property
New Kingston
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
Half Way Tree
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
Front of property
Casa Alexandria Guest Apartment

Casa Alexandria Guest Apartment

3.5 star property
Constant Spring
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
$258 nightly
The price is $278
Nov 20 - Nov 21
Total with taxes and fees
Casa Alexandria Guest Apartment
Exterior
New Kingston Serenity at The Oxford

New Kingston Serenity at The Oxford

New Kingston
8.8 out of 10, Excellent, (15)
"It was clean and the location was accessible "
United States
Damian
New Kingston Serenity at The Oxford
Outdoor pool
New Kingston Guest Apartments at Seymour

New Kingston Guest Apartments at Seymour

3.5 star property
New Kingston
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
$235 nightly
The price is $249
Nov 13 - Nov 14
Total with taxes and fees
New Kingston Guest Apartments at Seymour
Luxury Apartment, 2 Bedrooms, 2 Bathrooms | Bathroom | Combined shower/tub, free toiletries, hair dryer, towels
The Halifax Guest Apartment

The Halifax Guest Apartment

3.5 star property
Kingston
9.6 out of 10, Exceptional, (4)
"Is not an ideal place for a business trip since it is an apartment with no restaurants at walking distance. Be prepare for an additional charge of US$110 cash for cleaning and management charge. You need to call to arrange someone to meet you at the place as you arrive and as you leave (is not a hotel). The place is nice but is not a hotel."
United States
Nestor
$263 nightly
The price is $280
Nov 13 - Nov 14
Total with taxes and fees
The Halifax Guest Apartment
Premium Apartment, 2 Bedrooms, Ocean View, Executive Level | Private kitchen | Full-size fridge, microwave, oven, stovetop
New Kingston Guest Apartments II

New Kingston Guest Apartments II

3.5 star property
New Kingston
8.0 out of 10, Very Good, (24)
"Overall stay was great! could use a deep clean but it was ok."
United States
Shadaie
$275 nightly
The price is $293
Nov 13 - Nov 14
Total with taxes and fees
New Kingston Guest Apartments II
Exterior
Finest Accommodation Renfrew Place

Finest Accommodation Renfrew Place

3.0 star property
New Kingston
7.0 out of 10, Good, (2)
"The property was double booked the first two days leaving us without a place to stay. The property manager said he booked another place when we got there that was also not available. We spent several hours late in the evening until we were finally able to get a temporary booking. Communication was extremely poor overall it was hard initially to get a hold of the property owner although we had paid in advance our accommodations was not available first two days. "
United States
cornel
$170 nightly
The price is $186
Nov 13 - Nov 14
Total with taxes and fees
Finest Accommodation Renfrew Place
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

AC Hotel by Marriott Kingston, Jamaica

AC Hotel by Marriott Kingston, Jamaica

10/10 Excellent
"The accommodations were great. The staff was kind professional and attentive."
Jason 2-night trip
Posted 4 days ago
AC Hotel by Marriott Kingston, Jamaica

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 $93 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.