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Portland vacation rentals

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Top-rated vacation rentals in Portland

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

SUPERHOST
  1. Private room
  2. Portland
Private Bdrm in Huge Townhome Close to Everything!

Min 30 Day Stay Large, cozy bedroom in a 3 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 min 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 sedan or medium SUV possible -Laundry in building starting in Jan -PinPad Lock in Bdrm

$51 per night
SUPERHOST
  1. Entire guest suite
  2. East End
Garden Suite - A Peaceful Oasis on Munjoy Hill

Spacious light-filled garden level suite set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants & the Old Port. Tasteful art, a mini kitchen (fridge, microwave, toaster, coffee maker, electric kettle with coffee/tea and condiments), bath with essentials, contemporary furnishings: queen bed and bedding, leather reclining loveseat. Set in a lush garden of stone walls, pond, & perennials, this private, peaceful setting is a perfect homebase.

$84 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Spacious Monthly East End Remote Work Retreat Apt

Sunny, spacious, quiet location in the sought after East End. Perfect for breathing the sea air, working from home, and exploring the city! Ergonomic desk set up and room to spread out. Out door deck & Off street parking. Munjoy Hill living at its best! Easy walk to Old Port & downtown. City trails, award winning restaurants, including Rob Evans, plus Portland Food Coop, Whole Foods & shops, plus the Eastern Prom's epic views are steps away, including 4th of July Fireworks celebration.

$105 per night

Vacation rentals for every style

Get the amount of space that is right for you

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Portland summer vacation rentals

SUPERHOST
  1. Entire condo
  2. Arts District
Cozy Condo in West End Portland (Extended Stay)
$75 per night
SUPERHOST
  1. Entire cottage
  2. Portland
Cozy & Quiet Modern Cottage
$105 per night
  1. Entire rental unit
  2. East End
Cozy Studio on Munjoy Hill (Lic.#STHR-000186-2018)
$101 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Modern East End studio, perfect Portland home base
$96 per night
SUPERHOST
  1. Entire guest suite
  2. Portland
Deering Area Suite
$81 per night
SUPERHOST
  1. Entire loft
  2. Arts District
Sunny Arts Dist. Studio- Queen Bed & FREE Parking
$120 per night
SUPERHOST
  1. Entire loft
  2. West End
Port City Studio Loft (No Cleaning Fee)
$150 per night
  1. Private room
  2. Portland
Sunny room in Artistic Portland home dogs welcome!
$40 per night
  1. Entire rental unit
  2. Portland
Located in the heart of Portland!
$104 per night
SUPERHOST
  1. Entire guest suite
  2. East End
Private Suite in the Heart of East End Portland
$112 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Cozy, Private Apartment
$97 per night
SUPERHOST
  1. Entire loft
  2. Arts District
Spacious Studio in Arts District w/ Free Parking
$117 per night

Portland beach vacation rentals

SUPERHOST
  1. Entire rental unit
  2. East End
The Munjoy Hill Experience
$95 per night
SUPERHOST
  1. Entire rental unit
  2. East End
East End - MunjoyHill - Just Steps from Everything
$135 per night
SUPERHOST
  1. Private room
  2. Downtown Portland
Top of Portland's Munjoy Hill
$113 per night
SUPERHOST
  1. Entire guest suite
  2. East End
Quirky, Chic n Private East End Apt
$141 per night
SUPERHOST
  1. Private room
  2. Maine
By the Sea
$100 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Private Garden Retreat on Munjoy Hill
$156 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Private Hill Top Apartment Two/On Street Parking
$138 per night
  1. Entire rental unit
  2. East End
Beautiful Oceanside Apartment Prime Location
$168 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Hip & Cozy, high end Modern Design
$177 per night
SUPERHOST
  1. Entire rental unit
  2. Downtown Portland
Charming, Minimal Apartment on Munjoy Hill
$116 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Beachy 1BR Atop Munjoy Hill+Steps to Eastern Prom
$164 per night
SUPERHOST
  1. Entire rental unit
  2. East End
Tip Top of the East End
$179 per night

Portland winter vacation rentals

  1. Entire rental unit
  2. Portland
Vibrant Bayside, walk to all the action.
$121 per night
  1. Entire rental unit
  2. Arts District
1 Bedroom Apt in West End
$104 per night
  1. Entire rental unit
  2. West End
Stunning - modern 2 bedroom Victorian mansion pad
$150 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Spacious and Comfortable Private Apartment
$78 per night
  1. Entire rental unit
  2. Arts District
Fabulous Studio w/ Free Parking & Great Location
$128 per night
SUPERHOST
  1. Private room
  2. Portland
Our bright, cheery and sunfilled orange room
$75 per night
  1. Private room
  2. Portland
Artsy room in quiet cozy cottage near downtown
$58 per night
  1. Entire rental unit
  2. Arts District
Spacious Apartment Walkable to Downtown Portland
$120 per night
SUPERHOST
  1. Private room
  2. Portland
Queen bedroom and private bath
$65 per night
SUPERHOST
  1. Entire guesthouse
  2. Portland
The Carriage House at Libbytown
$130 per night
SUPERHOST
  1. Entire rental unit
  2. West End
West End Quitinete "MicroStudio" (No Cleaning Fee)
$145 per night
  1. Private room
  2. East End
Great space, great location: Munjoy Hill-East End!
$102 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.