Portland vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Portland

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

SUPERHOST
  1. Private room
  2. East End
Dog-Friendly Upstairs Room with Separate Entrance

Sunny, small, 2nd-floor private room, w/separate entrance, shared bath although mostly yours, small fridge & microwave, conveniently located in Portland's East End, close to restaurants, microbreweries, distilleries, Portland Trails, and the beach. Healthy walking distance to Old Port and downtown. Usually a lazy bones, my dog becomes Cujo when people arrive. Your pooch is welcome here, provided it is gentle with my grumpy senior cat.

$70 per night
SUPERHOST
  1. Private room
  2. Portland
1 Bedroom in Charming Victorian Townhouse

*MINIMUM 30 DAY RENTAL* Large, cozy bedroom in a 4 bedroom townhouse. The kitchen, living room, dining room and bathroom are shared spaces. Short walk to the Back Cove. 2 minutes to the Interstate and 5 minutes to the Old Port. Walk to the USM campus and Forest Avenue bars/ restaurants. Across the street from the USM gym where you can purchase a day pass or membership. -All utilities included - Off street parking for 1 medium SUV possible (must inquire) -Laundry in building starting in January

$70 per night
  1. Entire condo
  2. East End
Elegant condo w/ gas fireplace - walk to Portland's best restaurants & Old Port!

 

$193 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Cottages
  • Unique stays

Portland summer vacation rentals

SUPERHOST
  1. Entire rental unit
  2. East End
Spacious Monthly East End Remote Work Retreat Apt
$108 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Cozy + Walkable • East End Getaway
$166 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Modern East End studio, perfect Portland home base
$118 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Jonathan Smith 1814 Apartment
$92 per night
  1. Entire rental unit
  2. East End
Cozy Studio on Munjoy Hill (Lic.#STHR-000186-2018)
$130 per night
SUPERHOST
  1. Entire guest suite
  2. East End
Garden Suite - A Peaceful Oasis on Munjoy Hill
$74 per night
SUPERHOST
  1. Entire condo
  2. Arts District
Cozy Condo in West End Portland (Extended Stay)
$135 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Cute Studio Minutes from Downtown
$152 per night
  1. Private room
  2. Portland
Sunny room in Artistic Portland home dogs welcome!
$48 per night
SUPERHOST
  1. Entire rental unit
  2. Downtown Portland
Renovated 1 BR Downtown Apt w/backyard
$135 per night
  1. Private room
  2. Portland
Artsy room in quiet cozy cottage near downtown
$62 per night
SUPERHOST
  1. Private room
  2. Portland
Private Bdrm in Huge Townhome Close to Everything!
$100 per night

Portland winter vacation rentals

SUPERHOST
  1. Entire cottage
  2. Portland
Cozy & Quiet Modern Cottage
$188 per night
SUPERHOST
  1. Private room
  2. Portland
Queen bedroom and private bath
$74 per night
SUPERHOST
  1. Entire loft
  2. Arts District
Sunny Arts Dist. Studio- Queen Bed & FREE Parking
$191 per night
SUPERHOST
  1. Entire rental unit
  2. East End
East End - MunjoyHill - Just Steps from Everything
$135 per night
SUPERHOST
  1. Entire guesthouse
  2. Portland
The Carriage House at Libbytown
$130 per night
SUPERHOST
  1. Entire guest suite
  2. East End
Quirky, Chic n Private East End Apt
$179 per night
SUPERHOST
  1. Entire rental unit
  2. Arts District
Hidden Garden Apartment in Portlands West End
$225 per night
SUPERHOST
  1. Private room
  2. South Portland
Small clean room for one! Fragrance free home!
$65 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Cozy, Private Apartment
$94 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Sunny 1 BR Near Bus, Train & Town
$140 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Spacious and Comfortable Private Apartment
$106 per night
SUPERHOST
  1. Entire guest suite
  2. Portland
Deering Area Suite
$96 per night

Portland beach vacation rentals

SUPERHOST
  1. Entire rental unit
  2. East End
Remodeled, 1 block to breweries, just outside city
$179 per night
SUPERHOST
  1. Entire rental unit
  2. Old Port District
Beautiful Apt in Historic Building - Old Port
$249 per night
  1. Entire condo
  2. East End
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach!
$173 per night
  1. Entire condo
  2. Old Port District
Modern loft - Downtown, Steps from all the action!
$303 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Beachy 1BR Atop Munjoy Hill+Steps to Eastern Prom
$202 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Hip & Cozy, high end Modern Design
$271 per night
SUPERHOST
  1. Entire rental unit
  2. Downtown Portland
Beautiful Updated Apartment In Historic Townhouse
$207 per night
  1. Entire guest suite
  2. South Portland
Bright Guest Studio Near Lighthouses and Beach
$150 per night
  1. Entire rental unit
  2. East End
Beautiful Oceanside Apartment Prime Location
$260 per night
SUPERHOST
  1. Entire rental unit
  2. East End
"Nautica" on Munjoy Hill, Portland
$150 per night
SUPERHOST
  1. Entire loft
  2. Arts District
Charming Arts District Studio with Parking
$212 per night
SUPERHOST
  1. Hotel room
  2. Arts District
Inn at Park Spring 1 | Self Check In | Parking
$237 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.