Portland vacation rentals

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Latest Portland vacation rental deals

MOST POPULARPort Antonio
Vacation homes from $187

Best Portland vacation rentals

Most recommended vacation rentals in Portland

Show all
Jamaica House - The Blue Mountain Wilderness Retreat - Buff Bay - Bathroom
Jamaica House - The Blue Mountain Wilderness Retreat
Buff Bay, Jamaica
$68+
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Ridge View Cottage Blue Mountain Wilderness Retreat - Buff Bay - Balcony
Ridge View Cottage Blue Mountain Wilderness Retreat
Buff Bay, Jamaica
$87+
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Blissful Tides - Hope Bay - Dining room
Blissful Tides
Hope Bay, Jamaica
9.4Wonderful(5)
Parking
Free Wi-Fi
Pool
$816+
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Teejay's rustic retreat - Saint Margaret’s Bay - Balcony
Teejay's rustic retreat
Saint Margaret’s Bay, Jamaica
Free Wi-Fi
Spa
$202+
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Hidden next to the Blue mountain range - Port Antonio - Bedroom
Hidden next to the Blue mountain range
Port Antonio, Jamaica
$186+
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Entire Luxury Apartment with contemporary decor - Saint Margaret’s Bay - Beach
Entire Luxury Apartment with contemporary decor
Saint Margaret’s Bay, Jamaica
Free Wi-Fi
Spa
$252+
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Inn The Town - Port Antonio - Bedroom
Inn The Town
Port Antonio, Jamaica
8.5Very good(153)
Parking
Free Wi-Fi
$206+
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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
8.9Very good(9)
Parking
Free Wi-Fi
$70+
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Pimento Lodge Resort - Long Bay - Patio
Pimento Lodge Resort
Long Bay, Jamaica
9.1Wonderful(125)
Parking
Free Wi-Fi
Pool
$142+
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Buckingham Villa -Suites Full Kitchen-Rooms Variety - Buff Bay
Buckingham Villa -Suites Full Kitchen-Rooms Variety
Buff Bay, Jamaica
8.0Very good(1)
Parking
Free Wi-Fi
$153+
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Fairy Hill Palms - Port Antonio
Fairy Hill Palms
Port Antonio, Jamaica
8.4Very good(107)
Parking
Free Wi-Fi
$50+
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Sinopia Inn - Port Antonio
Sinopia Inn
Port Antonio, Jamaica
4.5Mediocre(53)
Parking
Free Wi-Fi
$99+
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Tha Lagoon Spot - Port Antonio
Tha Lagoon Spot
Port Antonio, Jamaica
6.7Okay(67)
Parking
Free Wi-Fi
Pool
Pet friendly
$55+
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Tha Lagoon Spot Caribbean Breeze - Port Antonio
Tha Lagoon Spot Caribbean Breeze
Port Antonio, Jamaica
5.4Fair(12)
Free Wi-Fi
Pool
Pet friendly
$61+
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Buff Bay Farms - Buff Bay
Buff Bay Farms
Buff Bay, Jamaica
9.0Wonderful(3)
Parking
Free Wi-Fi
$106+
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Roses place - Saint Mary
Roses place
Saint Mary, Jamaica
Parking
Free Wi-Fi
Pool
$96+
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$21 - $1,240$1,240 - $2,460$2,460 - $3,679$3,679 - $4,898$4,898+ per night

Property Types

ApartmentHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

November

High season

July

Average price (weeknight)

$87

Average price (weekend night)

$143
Cheapest month to stay with an average 73% drop in price.
Most expensive month to stay with an average 273% 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 (74% of total searches to Portland). The next most popular destinations are Long Bay (19%) and Boston (7%).

  • 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 $54. 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 $45 per night. Search here for similar prices

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

    The average price for a weekly Portland vacation rental found by KAYAK users in the last 2 weeks is $1,705.

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

    The average price for a monthly Portland vacation rental found by KAYAK users in the last 2 weeks is $7,306.

  • 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, houses, lodges, farm stays and villas.

  • What are some of the most-loved vacation rentals available in Portland?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Pimento Lodge Resort.

  • 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.

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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

Complete your trip to Portland

Vacations in Portland

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