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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.

Hotel room in West End
Morrill Mansion Inn | 7 | Self Check In | Parking
Welcome to The Morrill Mansion Inn! This 1800's era townhouse has been meticulously restored to its original Italianate elegance. Formerly the Morrill Mansion Bed & Breakfast, we recently dropped the breakfast to serve Airbnb guests near and far as a boutique hotel. Each room has a private ensuite bath, queen sized bed, smart TV (no cable but YouTube TV account), white noise machine, a reading chair (or couch depending on the room), mini fridge, & *one* parking spot for *compact cars* only.
$139 per night
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Rental unit in Portland
Bright & Spacious Apartment with Amazing Shower
Spend your vacation, work-trip, or weekend getaway in our lovely, downtown apartment. Apartment 3 is located on the third floor where you have access to all our modern appliances: refrigerator, microwave, dishwasher, washer and dryer combo unit. We have a luxurious shower, a queen bed in the bedroom, and a pull-out couch with a queen mattress in the living room. Both the bedroom and living room have large, flat-screen TVs and in the living room you will find a luxurious leather loveseat.
$182 per night
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Rental unit in West End
Huge Dreamy urban Artist-designed loft
Truly unique, Local Artist Designed 1 bedroom loft, very spacious, natural light filled 2 story apartment in an 1875 built Victorian home in the desirable west end historic neighborhood. Located a block from the Victorian mansion, a very central location, 10 minutes scenic stroll to renowned restaurants, situated just far enough from town for a more tranquil experience. birds sing. A very special spot full of character and charm. Views of the harbor from private deck. Driveway parking
$199 per night
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Stay near Portland's top sights

Photo of Portland Harbor Museum
Portland Harbor Museum349 locals recommend
Photo of Peaks Island
Peaks Island176 locals recommend
Photo of The Maine Mall
The Maine Mall86 locals recommend
Photo of DiMillo's On The Water
DiMillo's On The Water101 locals recommend
Photo of Fort Williams Park
Fort Williams Park229 locals recommend
Photo of Portland Museum of Art
Portland Museum of Art412 locals recommend

Portland summer vacation rentals

Condo in Downtown Portland
Modern Condo, Victorian Charm. Walk To Everything!
$195 per night
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Rental unit in Downtown Portland
Open Concept Loft in the Heart of Downtown Center
$218 per night
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Rental unit in East End
RETRO BnB in the Heart of East End Portland
$161 per night
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Rental unit in Downtown Portland
Central-Locale Studio in Vibrant Portland Maine!
$163 per night
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Rental unit in Downtown Portland
Bright Studio w/Own Entry in Downtown Portland
$204 per night
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Rental unit in East End
Hip & Cozy, high end Modern Design
$196 per night
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Condo in Downtown Portland
Stylish Downtown Condo
$168 per night
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Rental unit in East End
Beautiful Oceanside Apartment Prime Location
$189 per night
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Loft in West End
Port City Studio Loft
$158 per night
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Rental unit in East End
Beachy 1BR Atop Munjoy Hill+Steps to Eastern Prom
$211 per night
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Rental unit in East End
Portland, Munjoy Hill ~fresh, new & bright
$201 per night
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Condo in Downtown Portland
Luxury Condo in Downtown Portland Old Port
$215 per night
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Portland winter vacation rentals

Rental unit in Downtown Portland
Extraordinary Architectural Masterpiece Downtown
$236 per night
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Hotel room in Downtown Portland
Inn at Parkspring | Private entrance | Parking | 6
$134 per night
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Rental unit in West End
Quiet Retreat in the Heart of Portland's West End
$232 per night
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Hotel room in West End
Morrill Mansion Inn | 1 | Self Check In |
$98 per night
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Condo in Downtown Portland
Portland 1 Bedroom Condo in the Arts District.
$170 per night
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Guest suite in South Portland
The Bakery- Sunny studio - 1.5 mi to Portland
$150 per night
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Rental unit in Downtown Portland
Historic Home in the West End. Private Parking.
$254 per night
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Condo in Downtown Portland
Cozy Studio Urban Home with Queen Bed
$357 per night
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Hotel room in Downtown Portland
Inn at Parkspring 5 | Self Check In | Parking
$134 per night
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Rental unit in Downtown Portland
Charming West End Hideaway. Private Parking
$191 per night
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Private room in Maine
By the Sea
$120 per night
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Rental unit in Downtown Portland
Fabulous Studio w/ Free Parking & Great Location
$156 per night

Downtown Portland vacation rentals

Hotel room in West End
Skolfield Inn | Parking | Self-check-in | Garden 4
$116 per night
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Rental unit in East End
The Howard on Munjoy Hill
$174 per night
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Rental unit in Downtown Portland
Lovely Studio Walkable to Downtown Portland
$132 per night
Rental unit in East End
Parkside Retreat on Portland's Eastern Promenade
$219 per night
Rental unit in Downtown Portland
Downtown Portland 1 Bedroom
$179 per night
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Rental unit in West End
Cozy stylish West End apartment with parking
$183 per night
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Private room in Portland
White Oak Villa - Master Suite
$118 per night
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Hotel room in West End
Skolfield Inn | Parking | Self-check-in | Garden 2
$144 per night
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Guest suite in West End
West End Artist's Getaway
$188 per night
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Rental unit in East End
Tip Top of the East End
$198 per night
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Rental unit in East End
Portland, Munjoy Hill ~clean & stylish haven
$187 per night
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Rental unit in East End
Lovely Luxury and Cozy. Bay View. Walk to Old Port
$201 per night
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Stays in Peaks Island

Private room in Peaks Island
Carrabassett Lodge
$150 per night
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Guesthouse in Peaks Island
Island Cottage Hideaway, close to everything
$157 per night
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Private room in Peaks Island
Cozy Island room in a charming home
$185 per night
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Guest suite in South Portland
Apartment Near Willard Beach
$240 per night
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Stays in Downtown Portland

Condo in Downtown Portland
Coastal Penthouse - Center of Downtown Portland!
$344 per night
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Rental unit in West End
Charming West End Victorian
$236 per night
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Rental unit in Portland
Charming Downtown 1BR w/ Parking, Walk to Old Port
$346 per night
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Guest suite in Downtown Portland
Studio, Walk to everything, Parking
$197 per night
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Stays in Waterfront District

Rental unit in Downtown Portland
Old Port apartment
$160 per night
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Rental unit in East End
Amazing Views! Perfect Location. Loft style feel.
$240 per night
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Condo in Downtown Portland
Cozy 1 Bedroom Urban Home in the heart of Portland
$374 per night
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Hotel room in East End
Congress Queen | ADA Accessible
$163 per night
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Your guide to Portland

Introduction

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.


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, making it a popular time to stay in one of the area’s vacation rentals. 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.

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Portland