Portland Vacation Rentals from ￥15,361: Search Short-Term Rentals

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Our top choices for Portland vacation rentals

Windbreak Villa

Buff Bay

￥19,106 total

includes taxes & fees

May 27 - May 28

Perfect View - Entire House

Drapers

￥16,268 total

includes taxes & fees

May 30 - May 31

1 bedroom, iron/ironing board, free WiFi, bed sheets

Kai's Place @ Tim Pappies 3rd Floor luxury villa

Port Antonio

rohan k r.

￥19,690 total

includes taxes & fees

May 26 - May 27

Eco-Rustic Museum House & Art Stage between two beaches

Port Antonio

Andrew

￥12,336 total

includes taxes & fees

May 26 - May 27

Entire Luxury Apartment with contemporary decor

Port Antonio

￥41,227 total

includes taxes & fees

May 26 - May 27

Charming new 2 BR, 2 BR ocean view villa in Snow District, AC, private/secure

Snow District

￥45,805 total

includes taxes & fees

May 26 - May 27

Hope Bay-Peaceful getaway w/ pool and steps to natural beach

Hope Bay

Fiona L.

￥23,731 total

includes taxes & fees

May 26 - May 27

Port Antonio East Side Villa

Port Antonio

￥23,081 total

includes taxes & fees

May 26 - May 27

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Top Portland Hotel Reviews

ROK Hotel Kingston, Tapestry Collection by Hilton

10/10 Excellent

"One of the staff at the front desk was rude ..and at breakfast one attendant was rude thought we where there for brunch.. when ask for more fruits and a boil egg she told us none was left ..r she have to ask the chef.."

Frenchman's Cove Resort

8/10 Good

"The grounds were exceptional!! Beautiful, lush, vegetation and majestic mature trees. We enjoyed the bird songs in the morning. It is an easy walk to the pristine river/cove where the fresh water from the river meets the salt water of the ocean. The setting is serene. It allows you to be with your thoughts and could be a good place to write a book. The rooms, though spacious and habitable are in dire need of renovations. With renovations, Frenchman's Cove could be more than a Five Star hotel!"

S Hotel Kingston

10/10 Excellent

"I love how I was greeted by the staff at the reception area. The gentleman who offered me a drink was very polite and helpful in getting my luggage’s. I got my room upgraded as requested and I also got my bed restructured to my comfort level without any hassle from housekeeping. The supervisor (housekeeping) is a great asset in her dept, I think her name is Stacy omg she goes above and beyond to ensure that I was completely comfortable and satisfied. I enjoyed the breakfast and the different variety daily. All the staff are polite and amazing! I enjoyed my stay and will return in the future."

Great Huts

10/10 Excellent

"My family and I spent one night over our 4 day adventure in Portland. Our first time experiencing an eco-tourism type of accommodation. It was amazing. We stayed in the Fig Tree hut and all I can say is it is the best room of the house. They are undergoing some renovation but no disruption to our stay. The front desk staff, Tania was pleasant and accommodating with a late checkout. She even took it upon herself to verify if we wanted to place a dinner order to the kitchen prior to closure. We would visit again."

Jamaica Palace Hotel

8/10 Good

"I have stay here before and was very happy they could accommodate my family and I.. We booked another accommodation which was not as advertised… Breakfast is on point and with a wide choice. Room was clean and smells clean too… Great location to pop into town or to Boston beach… I will be back.. "

Find out more about Portland

Vacation Apartments in Portland

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All accommodation types in Portland

RV Parks in Portland

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Portland vacation rentals

Windbreak Villa

Perfect View - Entire House

Kai's Place @ Tim Pappies 3rd Floor luxury villa

Eco-Rustic Museum House & Art Stage between two beaches

Entire Luxury Apartment with contemporary decor

Charming new 2 BR, 2 BR ocean view villa in Snow District, AC, private/secure

Hope Bay-Peaceful getaway w/ pool and steps to natural beach

Port Antonio East Side Villa

Jamaica House - The Blue Mountain Wilderness Retreat

Ahh! (Pool/Ocean View Room w/ Private Bath)

Large home in Portland Parrish

The villa with ocean view

Teejay's rustic retreat

Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC

Ocean View Suite with Rooftop Lounge – Portland, Jamaica

The Ocean View Villa

Upstairs Room with Terrace at RobinHood guesthouse

Jeff's Downstairs Room at Robin Hood guesthouse

Blue Balcony Room at Robin Hood guest house

Downstairs Bedroom at Robin Hood guesthouse

Find vacation rentals that suit your style

Top Portland Hotel Reviews

ROK Hotel Kingston, Tapestry Collection by Hilton

Sea Cliff Resort

R Hotel Kingston

Frenchman's Cove Resort

S Hotel Kingston

Inn The Town

Great Huts

AC Hotel by Marriott Kingston, Jamaica

Jamaica Palace Hotel

Find out more about Portland

Vacation Apartments in Portland

Explore a world of travel with Expedia

Vacation Rentals in Portland

Change your mind

Treat yourself

Be picky

Our top choices for Portland vacation rentals

Windbreak Villa

Perfect View - Entire House

Kai's Place @ Tim Pappies 3rd Floor luxury villa

Eco-Rustic Museum House & Art Stage between two beaches

Entire Luxury Apartment with contemporary decor

Charming new 2 BR, 2 BR ocean view villa in Snow District, AC, private/secure

Hope Bay-Peaceful getaway w/ pool and steps to natural beach

Port Antonio East Side Villa

Jamaica House - The Blue Mountain Wilderness Retreat

Ahh! (Pool/Ocean View Room w/ Private Bath)

Large home in Portland Parrish

The villa with ocean view

Teejay's rustic retreat

Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC

Ocean View Suite with Rooftop Lounge – Portland, Jamaica

The Ocean View Villa

Upstairs Room with Terrace at RobinHood guesthouse

Jeff's Downstairs Room at Robin Hood guesthouse

Blue Balcony Room at Robin Hood guest house

Downstairs Bedroom at Robin Hood guesthouse

Find vacation rentals that suit your style

Top Portland Hotel Reviews

ROK Hotel Kingston, Tapestry Collection by Hilton

Find out more about Portland

Vacation Apartments in Portland

Explore a world of travel with Expedia