Portland holiday rentals

Search hundreds of travel sites at once for holiday home deals in Portland

Here is why travellers choose KAYAK

Free to useThere are no hidden charges or fees

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Useful Info
Recommended by KAYAK

Best Portland holiday rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

R361 - R19 764R19 764 - R39 184R39 184 - R58 586R58 586 - R77 989R77 989+ per night

Property Types

ApartmentCottageHomestayHouse

Search by freebies

Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Portland

Show all
Nature in portland - Port Antonio
Nature in portland
Port Antonio, Jamaica
6.1Okay(10)
Free Wi-Fi
R482+
Check availability
Port Antonio Residence - Port Antonio
Port Antonio Residence
Port Antonio, Jamaica
9.6Wonderful(47)
Free Wi-Fi
R602+
Check availability
Centrally Located Room - 5 - Port Antonio
Centrally Located Room - 5
Port Antonio, Jamaica
9.7Wonderful(79)
Parking
Free Wi-Fi
Air conditioning
R826+
Check availability
Fairy Hill Palms - Port Antonio
Fairy Hill Palms
Port Antonio, Jamaica
8.8Very Good(108)
Parking
Free Wi-Fi
R860+
Check availability
Tha Lagoon Spot - Port Antonio
Tha Lagoon Spot
Port Antonio, Jamaica
6.7Okay(71)
Parking
Free Wi-Fi
Pool
Pet-friendly
R946+
Check availability
Secluded self contained cabin close to Blue lagoon - Port Antonio - Beach
Secluded self contained cabin close to Blue lagoon
Port Antonio, Jamaica
9.0Wonderful(10)
Parking
Free Wi-Fi
R1 032+
Check availability
Tha Lagoon Spots Cool Vybz - Port Antonio
Tha Lagoon Spots Cool Vybz
Port Antonio, Jamaica
6.7Okay(21)
Free Wi-Fi
Pool
Pet-friendly
Air conditioning
R1 049+
Check availability
Long Bay, Rosehill View Garden - Port Antonio
Long Bay, Rosehill View Garden
Port Antonio, Jamaica
5.0Fair(1)
Parking
Free Wi-Fi
R1 238+
Check availability
I View - In Long Bay - Long Bay
I View - In Long Bay
Long Bay, Jamaica
9.3Wonderful(99)
Parking
Free Wi-Fi
Pet-friendly
Air conditioning
R1 290+
Check availability
Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway. - Port Antonio - Balcony
Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.
Port Antonio, Jamaica
7.5Good(2)
Free Wi-Fi
R2 099+
Check availability
Ridge Bay Chateau - Port Antonio - Patio
Ridge Bay Chateau
Port Antonio, Jamaica
8.5Very Good(8)
Free Wi-Fi
Air conditioning
R2 529+
Check availability
Inn The Town - Port Antonio - Bedroom
Inn The Town
Port Antonio, Jamaica
8.7Very Good(174)
Parking
Free Wi-Fi
Air conditioning
R2 632+
Check availability
Pimento Lodge Resort - Long Bay - Patio
Pimento Lodge Resort
Long Bay, Jamaica
9.2Wonderful(129)
Parking
Free Wi-Fi
Pool
Air conditioning
R2 993+
Check availability
A place in paradise - family villa on a peninsula directly by the sea - Port Antonio - Pool
A place in paradise - family villa on a peninsula directly by the sea
Port Antonio, Jamaica
9.7Wonderful(18)
Free Wi-Fi
R12 625+
Check availability
Gather,relax, and indulge at Chateau, in your stunning private villa sleeps 12 - Port Antonio - Living room
Gather,relax, and indulge at Chateau, in your stunning private villa sleeps 12
Port Antonio, Jamaica
Free Wi-Fi
Air conditioning
R13 795+
Check availability
Cocosan Villa - Port Antonio - Living room
Cocosan Villa
Port Antonio, Jamaica
Free Wi-Fi
Air conditioning
R84 697+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
April
R1 719
R1 500
Cheapest month to stay with an average 56% drop in price.
Most expensive month to stay with an average 53% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

FAQs when booking a holiday home in Portland

  • What types of holiday rentals are available in Portland?

    There are loads of different property types that you can make your holiday home in Portland. You’ll find apartments, agritourism, villas, homestays, cabins, houses, lodges and cottages.

  • Are there any pet-friendly holiday rentals in Portland?

    There are a number of dog and pet-friendly Portland holiday rentals, with around 4% allowing you to bring your pet along with you.

Where to stay in Portland?

Our map will help you find the perfect place to stay in Portland by showing you the exact location of each holiday home.

Everything you need to know for your stay in Portland

Not what you’re looking for? Find thousands of other hotels, flights and car hire with KAYAK.