Portland vacation rentals

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Best Portland vacation rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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C$ 0 - C$ 1,624C$ 1,624 - C$ 3,247C$ 3,247 - C$ 4,870C$ 4,870 - C$ 6,493C$ 6,493+ per night

Property Types

ApartmentCottageHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Portland

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Inn The Town - Port Antonio - Bedroom
Inn The Town
Port Antonio, Jamaica
8.6Very good(160)
Parking
Free Wi-Fi
C$ 238+
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Pimento Lodge Resort - Long Bay - Patio
Pimento Lodge Resort
Long Bay, Jamaica
9.1Wonderful(126)
Parking
Free Wi-Fi
Pool
C$ 316+
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The villa with ocean view - Manchioneal - Balcony
The villa with ocean view
Manchioneal, Jamaica
C$ 80+
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The room of the city of Ioannis Paradisos 1 - Port Antonio - Bedroom
The room of the city of Ioannis Paradisos 1
Port Antonio, Jamaica
C$ 78+
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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
C$ 118+
Check availability
Cozy 2BR Port Antonio Retreat with stunning sea views - Port Antonio - Beach
Cozy 2BR Port Antonio Retreat with stunning sea views
Port Antonio, Jamaica
6.6Okay(3)
Parking
Free Wi-Fi
C$ 163+
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Secluded self contained cabin close to Blue lagoon - Port Antonio - Beach
Secluded self contained cabin close to Blue lagoon
Port Antonio, Jamaica
9.1Wonderful(9)
Free Wi-Fi
C$ 106+
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Tha Lagoon Spot - Port Antonio
Tha Lagoon Spot
Port Antonio, Jamaica
6.8Okay(68)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 76+
Check availability
I View - In Long Bay - Long Bay
I View - In Long Bay
Long Bay, Jamaica
9.3Wonderful(97)
Parking
Free Wi-Fi
Pet friendly
C$ 102+
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Fairy Hill Palms - Port Antonio
Fairy Hill Palms
Port Antonio, Jamaica
8.6Very good(108)
Parking
Free Wi-Fi
C$ 69+
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Tha Lagoon Spot Caribbean Breeze - Port Antonio
Tha Lagoon Spot Caribbean Breeze
Port Antonio, Jamaica
6.6Okay(13)
Free Wi-Fi
Pool
Pet friendly
C$ 84+
Check availability
Sinopia Inn - Port Antonio
Sinopia Inn
Port Antonio, Jamaica
4.5Mediocre(53)
Parking
Free Wi-Fi
C$ 136+
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Port Antonio Residence - Port Antonio
Port Antonio Residence
Port Antonio, Jamaica
9.7Wonderful(38)
Free Wi-Fi
C$ 41+
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Tha Lagoon Spots Cool Vybz - Port Antonio
Tha Lagoon Spots Cool Vybz
Port Antonio, Jamaica
7.0Good(21)
Free Wi-Fi
Pool
Pet friendly
C$ 84+
Check availability
Kai's Place at Tim Pappies 3rd Floor luxury villa - Port Antonio
Kai's Place at Tim Pappies 3rd Floor luxury villa
Port Antonio, Jamaica
9.7Wonderful(18)
Parking
Free Wi-Fi
Pool
Pet friendly
C$ 155+
Check availability
Hunter's Place - Tim Pappies - Port Antonio
Hunter's Place - Tim Pappies
Port Antonio, Jamaica
9.0Wonderful(7)
Parking
Free Wi-Fi
Pet friendly
C$ 174+
Check availability
Useful Info

Good to know

Low season

July

High season

May

Average price (weeknight)

C$ 180

Average price (weekend night)

C$ 120
Cheapest month to stay with an average 79% drop in price.
Most expensive month to stay with an average 92% 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 vacation home in Portland

  • What is the most popular vacation rental destination in Portland?

    Based on KAYAK vacation rental searches, the most popular destination is Port Antonio (100% of total searches to Portland).

  • How much is a vacation rental in Portland for tonight?

    In the last 72 hours, users have found Portland vacation rentals for tonight for as low as C$ 134. Search here for similar prices

  • How much is a vacation rental in Portland for this weekend?

    In the last 72 hours, users have found Portland vacation rentals for this weekend for as low as C$ 114 per night. Search here for similar prices

  • What types of vacation rentals are available in Portland?

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

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

    There are a number of dog and pet-friendly Portland vacation rentals, with around 8% 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 vacation home.

Everything you need to know for your stay in Portland

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