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Portland holiday rentals

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Best Portland vacation rentals

Most recommended vacation rentals in Portland

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Island View House Bnb Self Check-In - Portland - Building
Island View House Bnb Self Check-In
Portland, ME, United States
8.6Very Good(65)
Parking
Free Wi-Fi
$527+
View availability
Rent a room in the gorgeous Holt House - Portland - Building
Rent a room in the gorgeous Holt House
Portland, ME, United States
Free Wi-Fi
$353+
View availability
Inn at Park Spring 1 - Self Check In - Parking - Portland - Building
Inn at Park Spring 1 - Self Check In - Parking
Portland, ME, United States
Free Wi-Fi
$726+
View availability
Beautiful 1st Floor Apartment & Amazing Shower - Portland - Living room
Beautiful 1st Floor Apartment & Amazing Shower
Portland, ME, United States
Free Wi-Fi
$554+
View availability
East End Annex - Portland - Bedroom
East End Annex
Portland, ME, United States
9.1Wonderful(20)
$445+
View availability
East end. Walk to food, beer and downtown fun. - Portland - Living room
East end. Walk to food, beer and downtown fun.
Portland, ME, United States
9.2Wonderful(37)
Free Wi-Fi
$562+
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Beautifully Spacious with Charm - Portland - Living room
Beautifully Spacious with Charm
Portland, ME, United States
Free Wi-Fi
$256+
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Luxury Condo Downtown Portland Old Port - Portland - Building
Luxury Condo Downtown Portland Old Port
Portland, ME, United States
Free Wi-Fi
$692+
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Spacious and Contemporary Condo in the Heart of Portland - Close to Beach - Portland - Living room
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Portland, ME, United States
Free Wi-Fi
$472+
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Elegant condo - walk to Portland's best restaurants & Old Port - Portland - Kitchen
Elegant condo - walk to Portland's best restaurants & Old Port
Portland, ME, United States
$524+
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Fabulous studio apartment with roof deck - Portland - Patio
Fabulous studio apartment with roof deck
Portland, ME, United States
Free Wi-Fi
Pet-friendly
$486+
View availability
Inn at Park Spring 3 - Self Check In - Parking - Portland - Living room
Inn at Park Spring 3 - Self Check In - Parking
Portland, ME, United States
Free Wi-Fi
$636+
View availability
The Brew House - 2nd Floor Private Apartment - Portland
The Brew House - 2nd Floor Private Apartment
Portland, ME, United States
9.5Wonderful(23)
Parking
Free Wi-Fi
$689+
View availability
Charming Victorian, Perfect location , private deck. - Portland
Charming Victorian, Perfect location , private deck.
Portland, ME, United States
Pet-friendly
$596+
View availability
Cumberland Casa - B - Portland
Cumberland Casa - B
Portland, ME, United States
6.4Okay(7)
$377+
View availability
Victorian Parlor Suite - Portland
Victorian Parlor Suite
Portland, ME, United States
Pet-friendly
$383+
View availability
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KAYAK’s insights for holiday rentals in Portland

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Portland with confidence.

Which month has the cheapest vacation rental rates in Portland?

Vacation rentals are cheapest in Portland in January, with average rates of $377. In comparison, July is the most expensive month, with prices at $1,270.

What is the cheapest day of the week to book a vacation rental in Portland?

Sunday offers the lowest rates in Portland, with an average nightly price of $396. The highest prices are found on Thursday, with average rates at $818.

How early should you book a vacation rental in Portland?

Book at least 43 days before your stay begins to get the best price for your Portland vacation rental.
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Good to know

Low season

April

High season

April

Average price (weekend night)

$292
Cheapest month to stay with an average 0% drop in price.
Most expensive month to stay with an average 0% rise in price.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Portland holiday rental deals

  • If you want to enjoy some local history on your trip, you should look for Portland holiday rentals that are in the centre of the city, where many of the main attractions are. For example, West End Retreat @ The Arts District is located a short walk from Victoria Mansion, which is a popular historical landmark.
  • For those that want to enjoy some of the best food that the city has to offer, you should look for Portland holiday rentals that are near East Bayside. For instance, Panoramic Water, Island & City Views W/Private Roof Deck is located only a short distance from popular eateries like Chong Tu Bot and Terlingua.
  • If want to enjoy a holiday by the coast, you should look for Portland house rentals that are close to the beach. For example, Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants is only about a 10min walk to East End Beach, which is a calm beach that offers a range of activities.
  • To make the most of the hiking trails that are in the city, you should look for Portland holiday rentals in the East End. For example, if you stayed at Enjoy Portland With Family or Friends, you would be close to popular walks like the Eastern Promenade Trail.
  • If you are looking to hire a car during your visit to Portland, you should look for properties that provide you with parking areas. For instance, Adorable Portland Getaway on the Eastern Promenade typically provides parking spaces to its guests.
  • Pet-friendly, air-conditioned, pool, beachfront, and hot tub are the most popular holiday rental property amenities in Portland
  • Holiday rentals in Portland are around 61% more expensive than hotels on average. Search here to compare prices for all accommodation types in Portland.
  • The best holiday rental properties in Portland are Brand New 1 Bedroom Apartment in Portland (10.0, 26 reviews), The Globe House on Munjoy Hill - Walk to Breweries (10.0, 42), and Completely remodeled 2 bedroom apartment in Portland's West End (10.0, 29), based on ratings and reviews from real travellers.
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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, cabins, campgrounds, caravan parks, chalets, condos, cottages, houses, campsites, homestays, lodges, luxury tents and villas.

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

    If you’re looking for something special, the holiday rental most loved by KAYAK users is Econo Lodge Freeport - Brunswick Area.

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

    There are a number of dog and pet-friendly Portland holiday rentals, with around 15% allowing you to bring your pet along with you.

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

    In the last 72 hours, users have found Portland holiday rentals for tonight for as low as $244. Search here for similar prices

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

    In the last 72 hours, users have found Portland holiday rentals for this weekend for as low as $366 per night. Search here for similar prices

  • How can I find holiday rentals near me in Portland?

    Take a look at our holiday rentals map to find the best holiday rental homes near you.

  • What are the benefits of a self-catered property?

    When you’re in the U.S. you will find that there are many great places to eat, but it can be expensive to eat out every day. If you get a self-catered property, you’ll have the option to dine in whenever you fancy. For example, Glorious Getaway On Portland's Eastern Promenade provides facilities like an oven and cooktop, so you can cook as much as you like. There is also a range of shops nearby, where you can pick up fresh ingredients for your stay.

  • Where is best to stay in Portland for nightlife?

    If you want to go to the best bars and pubs, you should look for accommodation that’s in the centre of the city. For example, Bright & Spacious Apartment with Amazing Shower is only a short distance from popular establishments like Blackstones and The Jewel Box.

  • What options are there for Portland properties that have swimming pools?

    If you want to swim but prefer to avoid the sea, you will be pleased to know that there are properties that have pools. For example, Close To Downtown With Hot Tub! has an outdoor pool for its guests as well as a spa for you to use.

  • Where is best to stay to be close to the airport?

    If you want to be close to Portland International Jetport (PWM), then you should stay close to Highway 95, so you’ll be close to the terminal. For example, Beautifully Spacious with Charm is about a 12min drive from the airport.

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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 holiday rental.

Everything you need to know for your stay in Portland

Portland holiday rental deals. Search for holiday homes, apartments, condos, cabins, cottages, villas and more in Portland. Find cheap holiday homes to rent in Portland. KAYAK searches hundreds of travel sites to help you find and book a holiday rental in Portland that suits you best.

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