Skip to content

Portland Maine

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness, and more.

West End gem. Close to medical center.
Entire rental unit · 2 guests · 1 bed · 1 bath
West End gem. Close to medical center.This is a restored 1890’s home on the Prestigious West End in Portland . You are just a block from the Western Promenade which is a tourist attraction to watch the sunset over the White Mountains in NH; people often picnic here depending on the season. While on the Prom you will see rows of mansions that have been preserved, feel free to walk the neighborhoods on a house/ garden tour, or around the Western Cemetery.
Modern Studio Loft w/ Parking in Perfect Location
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath
Modern Studio Loft w/ Parking in Perfect Location2021 City of Portland registration STHR 000854 This spacious comfortable studio loft is in the heart of Portland's Arts District on the quieter end of Oak Street within walking distance to almost everything. Complementary parking for one car is provided in a nearby lot.
Sophisticated Charm at an unbeatable price!
SUPERHOST
Entire rental unit · 4 guests · 2 beds · 1 bath
Sophisticated Charm at an unbeatable price!Apartment is centrally located to all downtown amenities and transportation system. Located in the beautiful West End on a quiet residential street approximately 1 mile from the downtown area. Apartment (3rd floor) gets beautiful sun throughout and has all of the traditional charm and character of the West End homes but updated bathroom and kitchen, both recently remodeled in 2017. Rental includes access to one parking space and shared outdoor area to enjoy during your stay. STHR-001018-2019

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Portland vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Portland

SUPERHOST
  1. Entire loft
  2. Portland
Sunny Arts Dist. Studio- Queen Bed & FREE Parking
$123 per night
PLUS
  1. Entire residential home
  2. Portland
Explore Portland from a 18th-Century Victorian
$165 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Bright and cozy Munjoy Hill neighborhood apartment
$175 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Bright 1 bdrm in the Arts District w/free parking
$138 per night
PLUS
  1. Entire guest suite
  2. Portland
Sunny West End Guest Suite with Harbor Views
$206 per night
SUPERHOST
  1. Private room
  2. Maine
By the Sea
$98 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Spacious and Comfortable Private Apartment
$63 per night
SUPERHOST
  1. Entire cottage
  2. Portland
Cozy & Quiet Modern Cottage
$145 per night
SUPERHOST
  1. Entire guest suite
  2. Portland
Deering Area Suite
$71 per night
  1. Entire rental unit
  2. Portland
Fabulous Studio w/ Free Parking & Great Location
$144 per night
  1. Entire cottage
  2. Portland
"Heart's Content" Peaks' Pup Friendly Cottage
$318 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Downtown Apartment w/ Parking - Come Work or Play!
$141 per night

Your guide to Portland

All About Portland

Perched along the dramatic slate-gray waters of the Atlantic Ocean, where gulls wheel and whitecaps dot the surf, Portland is quintessential Maine combined with the allures of a metropolis. Established as a booming port town by traders and fishermen, Portland is now the state’s biggest city. Here you can tread cobblestone streets, visit historic lighthouses, and dine on lobsters hauled from the nearby waters. But you’ll also find top-notch museums and galleries, boutique shopping, and a celebrated foodie scene that boasts award-winning restaurants and a thriving microbrew culture. New and old Maine commingle comfortably here, where you can enjoy the best of both worlds.


How do I get around Portland?

Fly into Portland International Jetport (PWM), located about 15 minutes from downtown. You can explore this walkable city on foot — particularly the Arts District and Old Port, which are next to each other. The Greater Portland Metro operates several bus lines that navigate the city, and taxis and rideshares are also easily found. Renting a car is a good idea if you plan to explore nearby towns and attractions, such as the Portland Head Light.


When is the best time to stay in a vacation rental in Portland?

Summers are brief and mild in Portland, where June through September bring average temperatures in the 70s Fahrenheit. October and November cool down, with temperatures in the 40s and 50s, and December through February are chilly, with temperatures in the 30s. Things grow steadily warmer starting in March, ushering in 40-degree weather and climbing into the low 60s by May. You’re likely to encounter rainfall year-round, and snow December through March. Pack lots of warm layers, hats, and scarves.


What are the top things to do in Portland?

Portland Head Light

The Portland area is home to several historic lighthouses, but the Portland Head lighthouse is the undisputed heavyweight. Construction began in 1790, making it the oldest in the state. Visitors can tour the quaint lighthouse and its grounds, which include the former keepers’ house, now repurposed as a museum. Take in the sweeping vista, which includes views of four more lighthouses and the possibility of watching lobstermen pulling their traps from the bay, before taking a scenic stroll through Fort Williams, the 90-acre park in which the lighthouse resides.

Casco Bay and the Calendar Islands

Hop on a ferry (or charter a water taxi) to tour the photogenic Calendar Islands, clustered in grand Casco Bay. You can experience small-town Maine life here. Teensy Cliff Island has fewer than 60 year-round residents and a small schoolhouse. Peaks Island offers four miles of uninterrupted coastline and historical sites such as a World War II artillery bunker. Tonier Great Diamond Island, where a private community has been installed within the refurbished military buildings of historic Fort McKinley, boasts upscale dining. Don’t have time to set ashore? Casco Bay Lines, the island ferry service, offers speciality cruises that will afford you a sailor’s-eye view of the islands and dazzling bay.

Old Port District

Travel back in time in this quaint maritime neighborhood that still looks very much the way it did in the early 19th century. Narrow cobblestone streets and historic brick warehouses lend the enclave its cozy feel, but that’s where the frozen-in-time vibe ends. The restored Old Port District, which is on the National Register of Historic Places, is home to quirky boutiques, inventive eateries, and brewpubs. You’ll find many of these offerings on buzzy Exchange Street.