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.

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SUPERHOST
Private room · Portland
Spacious, Private Bedroom- Close to Everything!
Minimum 30 Day Stay 250+ square feet of private bedroom space! Great location- close to interstate, downtown, Back Cove, USM and local bars and restaurants. Great place to stay for grad students, travel nurses or other transient professionals! -Bedroom has Pin Pad lock for address safety and privacy -Laundry in building
$56 per night
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Entire rental unit · Downtown Portland
Third-floor condo steps from dining & Old Port with balcony, AC, harbor view
 
$201 per night
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Entire condo · East End
Elegant condo w/ gas fireplace - walk to Portland's best restaurants & Old Port!
 
$184 per night

Vacation rentals for every style

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Stay near Portland's top sights

Photo of Peaks Island
Peaks Island116 locals recommend
Photo of Fort Williams Park
Fort Williams Park108 locals recommend
Photo of Portland Head Lighthouse
Portland Head Lighthouse120 locals recommend
Photo of Portland Museum of Art
Portland Museum of Art170 locals recommend
Photo of Bug Light Park
Bug Light Park59 locals recommend
Photo of Casco Bay Lines
Casco Bay Lines54 locals recommend

Portland summer vacation rentals

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SUPERHOST
Entire rental unit · Arts District
Modern Studio Loft w/ Parking in Perfect Location
$163 per night
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SUPERHOST
Entire rental unit · East End
Modern East End studio, perfect Portland home base
$138 per night
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SUPERHOST
Entire rental unit · East End
East End - MunjoyHill - Just Steps from Everything
$135 per night
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Entire rental unit · Portland
Comfortable two bedroom Apartment
$78 per night
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SUPERHOST
Entire rental unit · East End
Cozy Studio on Munjoy Hill (Lic.#STHR-000186-2018)
$130 per night
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SUPERHOST
Entire rental unit · West End
Location, location!
$103 per night
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SUPERHOST
Entire guest suite · East End
Quirky, Chic n Private East End Apt
$141 per night
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SUPERHOST
Entire guesthouse · Portland
The Carriage House at Libbytown
$130 per night
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Entire rental unit · West End
Stunning - modern 2 bedroom Victorian mansion pad
$150 per night
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Private room · South Portland
Cozy private guest suite attached to owner’s home.
$75 per night
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SUPERHOST
Entire rental unit · East End
Cozy + Walkable • East End Getaway
$166 per night
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SUPERHOST
Entire rental unit · Old Port District
Beautiful Apt in Historic Building - Old Port
$225 per night

Portland winter vacation rentals

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SUPERHOST
Entire loft · Arts District
Charming Arts District Studio with Parking
$187 per night
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Entire loft · Portland
Lily's Loft; Charming one bedroom studio
$182 per night
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SUPERHOST
Entire guest suite · East End
Garden Suite - A Peaceful Oasis on Munjoy Hill
$81 per night
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SUPERHOST
Entire rental unit · Portland
Spacious and Comfortable Private Apartment
$109 per night
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Entire rental unit · Old Port District
Lovely studio in heart of Old Port
$153 per night
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SUPERHOST
Entire guest suite · Portland
Deering Area Suite
$113 per night
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SUPERHOST
Entire rental unit · Portland
Private 1 Bedroom Apt Close to the Old Port
$132 per night
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Entire rental unit · West End
King Size Bed ♦ West End Studio ♦ Walk to Old Port
$120 per night
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Entire condo · East End
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach!
$164 per night
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SUPERHOST
Entire rental unit · East End
Beachy 1BR Atop Munjoy Hill+Steps to Eastern Prom
$210 per night
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Entire rental unit · East End
The Aerie
$150 per night
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SUPERHOST
Entire rental unit · West End
West End gem. Close to medical center.
$189 per night

Portland beach vacation rentals

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SUPERHOST
Entire rental unit · East End
Remodeled, 1 block to breweries, just outside city
$180 per night
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Entire condo · Old Port District
Modern loft - Downtown, Steps from all the action!
$330 per night
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Entire condo · East End
Polished condo with balcony - walk to Eastern Promenade & Casco Bay
$145 per night
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Entire condo · Old Port District
Explore Old Port on foot frm comfy downtown condo
$232 per night
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SUPERHOST
Entire rental unit · Arts District
Bright Studio w/Own Entry in Downtown Portland
$189 per night
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Entire rental unit · West End
BEST location! HUGE 1 bedroom downtown Portland
$153 per night
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SUPERHOST
Private room · Downtown Portland
Top of Portland's Munjoy Hill
$126 per night
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Entire guest suite · South Portland
Bright Guest Studio Near Lighthouses and Beach
$150 per night
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SUPERHOST
Entire guest suite · East End
Private Suite in the Heart of East End Portland
$175 per night
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SUPERHOST
Entire rental unit · East End
Eastern Promenade Getaway
$295 per night
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Entire condo · East End
Sleek & newly-renovated third-floor condo w/ amazing water views - walk to bay
$131 per night
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SUPERHOST
Entire rental unit · Downtown Portland
Charming, Minimal Apartment on Munjoy Hill
$164 per night

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.

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