Search Holiday Rentals in Portland

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Top Holiday Rentals in Portland

Pearl Ocean Villa

3.5 star property
10.0 out of 10, Exceptional, (1)
"Cleanest the hoast was superb"
Pearl Ocean Villa

San Cove, Blue Lagoon, Port Antonio 4BR

3.0 star property
San Cove, Blue Lagoon, Port Antonio 4BR

Abacus Jamaica the Zana Suite

3.0 star property
8.2 out of 10, Very good, (55)
"My hostess Novelette was very cooperative and eager to ensure my stay went well. She was always ready to answer any questions asked to make my stay comfortable. I would certainly stay here again should the opportunity arise."
The price is ฿2,419
฿3,982 total
includes taxes & fees
5 May - 6 May
Abacus Jamaica the Zana Suite

Reggae Legends Estate

2.5 star property
9.4 out of 10, Exceptional, (3)
"Getting up on the hill was definitely a new experience but the place , view and employees were amazing. Owner himself made sure we had everything we needed , accommodated when needed even suggested places we should visit. Loved the experience and view was breath taking "
The price is ฿8,305
฿9,584 total
includes taxes & fees
7 May - 8 May
Reggae Legends Estate

The Gardens

3.0 star property
7.0 out of 10, Good, (48)
"Lovely place overall. Tricky on gps pwr how the address comes up Amazing hostess and staff! Room was quite dusty, evwn mh cups, needed trashcans, and no outlet for TV to work. Didn't matter, quick stay!"
The price is ฿3,335
฿3,702 total
includes taxes & fees
9 May - 10 May
The Gardens

CTBH at EI8HT Super Studios

3.0 star property
8.0 out of 10, Very good, (1)
"I would stay at this property again. 10 out of 10 for cleanliness. We stayed in the loft apartment and we enjoyed our stay, very modern and spacious. Property is safe and secure and close to lots of dinning options "
CTBH at EI8HT Super Studios

Cattleya's New Kingston Guest Apartment

3.5 star property
8.6 out of 10, Excellent, (55)
"Worth it"
Cattleya's New Kingston Guest Apartment

New Kingston's Deluxe Apartment

3.5 star property
8.8 out of 10, Excellent, (45)
"This property was great. I would stay there again "
New Kingston's Deluxe Apartment

The Dorchester

3.0 star property
7.2 out of 10, Good, (13)
"The property was great . I enjoyed my stay and will surely return in the future. "
The Dorchester

New Kingston Corporate Apts at Donhead

3.5 star property
9.6 out of 10, Exceptional, (30)
"Property manager force is to check out before time also never gave me my deposit money back etc also no respect "
New Kingston Corporate Apts at Donhead

Sweet Kensville

4.0 star property
10.0 out of 10, Exceptional, (2)
"Great stay"
The price is ฿4,334
฿7,359 total
includes taxes & fees
29 May - 30 May
Sweet Kensville

Casa Royale Guest Apartment

3.5 star property
9.6 out of 10, Exceptional, (67)
"Place was very clean and comfortable."
The price is ฿4,773
฿8,596 total
includes taxes & fees
2 May - 3 May
Casa Royale Guest Apartment

Apartment with roof top pool

3.0 star property
9.0 out of 10, Wonderful, (2)
"Property was very clean and within walking distance to variety of eatery. Some units had balconies. If I could change anything I would make sure I have balcony "
The price is ฿3,227
฿7,374 total
includes taxes & fees
10 May - 11 May
Apartment with roof top pool

Lovely 2-bed Apartment in the New Kingston Area

3.0 star property
10.0 out of 10, Exceptional, (1)
"I liked the area the property was clean ,my dislikes was the fact there was no elevator and the parking space there was not one assigned for that particular apartment. "
Lovely 2-bed Apartment in the New Kingston Area

The Country Club Villa I

3.5 star property
9.0 out of 10, Wonderful, (10)
"The management team was awesome, the AC didn’t work in the main room on the first night but Ms Vicki made sure that I didn’t go a second night without it."
The price is ฿4,645
฿8,442 total
includes taxes & fees
13 May - 14 May
The Country Club Villa I

Lilford Mews Suites

3.5 star property
8.0 out of 10, Very good, (11)
"Nice place, clean, great furniture, good price. Need to get better the communication"
Lilford Mews Suites

Bayfront Villas and Apt

3.0 star property
7.4 out of 10, Good, (6)
"By far the worst rental Ive ever booked. We booked for 11/6-11/12 during a trip to bury my aunt. I contacted the host to let her know that our flight would be landing at 3am Thurs morning. She asked if someone could pick up the keys. When we arrived after 4am, already exhausted, we get upstairs and the keys did not work. We had to wait almost an hour for the host to bring the correct keys. When we were finally able to get into the apartment, we were met with shock & confusion. The air...
The price is ฿3,913
฿10,385 total
includes taxes & fees
31 May - 1 Jun
Bayfront Villas and Apt

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...
The price is ฿4,548
฿9,766 total
includes taxes & fees
1 May - 2 May
Casa Alexandria Guest Apartment

Charming 1-bedroom House in St Thomas Jamaica

3.5 star property
The price is ฿1,654
฿1,654 total
includes taxes & fees
7 May - 8 May
Charming 1-bedroom House in St Thomas Jamaica

New Kingston Guest Apt at Dorchester

3.5 star property
8.4 out of 10, Very good, (5)
"It was great love it "
The price is ฿4,662
฿8,463 total
includes taxes & fees
9 May - 10 May
New Kingston Guest Apt at Dorchester
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.
Don't see what you're looking for?
See all available properties in Portland
Save an average of 15% on thousands of hotels when you're signed in