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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.
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Popular amenities for Portland vacation rentals
Portland beach vacation rentals
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Guest suite in South Portland
5 out of 5 average rating, 706 reviewsOceanfront with amazing views and private entrance
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Rental unit in Yarmouth
4.96 out of 5 average rating, 100 reviewsSweet 1-Bedroom Apartment in Vintage Village Cape
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Guest suite in Saco
4.93 out of 5 average rating, 396 reviewsBarn-Board Abode (private studio) powered by solar
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Guest suite in Portland
4.93 out of 5 average rating, 434 reviewsSpacious Comfortable Deering Oaks Suite
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Rental unit in East End
4.9 out of 5 average rating, 363 reviewsHip & Cozy, high end Modern Design
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Rental unit in Downtown Portland
4.85 out of 5 average rating, 178 reviewsLovely studio in downtown Portland
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Rental unit in East End
4.97 out of 5 average rating, 417 reviewsBright and cozy Munjoy Hill neighborhood apartment
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Rental unit in Downtown Portland
4.93 out of 5 average rating, 160 reviewsGarden Apartment Close to Everything
Private Portland vacation rentals
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Home in Portland
4.95 out of 5 average rating, 304 reviewsExplore Portland from a 18th-Century Victorian
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Guest suite in Scarborough
4.98 out of 5 average rating, 143 reviewsBeautiful, private apartment!! Great location!
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Guest suite in Cumberland
4.92 out of 5 average rating, 119 reviewsSpringer Park! adorable guesthouse very stylish!
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Cottage in Scarborough
4.97 out of 5 average rating, 175 reviewsBright, clean, private cottage near Higgins Beach!
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Cabin in Scarborough
4.81 out of 5 average rating, 170 reviewsTiny Cottage Across The Street From Beach
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Guest suite in Kennebunk
4.99 out of 5 average rating, 199 reviewsThe Nest! VERY CLEAN! Near downtown! Self check-in
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Serviced apartment in Topsham
4.92 out of 5 average rating, 103 reviewsPrivate, Cozy, Deep Soaking Tub
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Cabin in Lovell
4.96 out of 5 average rating, 273 reviewsSecluded, cozy cabin nestled in the Maine woods
Portland house rentals
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Home in Auburn
4.99 out of 5 average rating, 135 reviewsCozy getaway near Bates & the best spots in Maine
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Home in Lebanon
4.96 out of 5 average rating, 174 reviewsTranquility, Relaxation, Family, Romance
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Home in Edgecomb
4.95 out of 5 average rating, 412 reviewsSheepscot Harbour Cottage/waterview
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Home in Lewiston
4.98 out of 5 average rating, 153 reviewsClean and comfortable home
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Home in Portland
4.97 out of 5 average rating, 143 reviewsQuiet Comfy Victorian Escape
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Home in Freeport
4.85 out of 5 average rating, 254 reviewsHome On Pond in Woods - Guest Suite
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Home in Westbrook
4.89 out of 5 average rating, 469 reviewsReno Barn w/ a lot of Charm! Breweries & Airport
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Home in Saco
5 out of 5 average rating, 129 reviewsOceanfront w/ Stunning views and Private Deck☀️🏖
Quick stats about vacation rentals in Portland
Total rentals
1.5K properties
Total number of reviews
153K reviews
Family-friendly rentals
780 properties are a good fit for families
Pet-friendly rentals
390 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
750 properties have a dedicated workspace
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.
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.
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.
Frequently Asked Questions
How is the weather in Portland?
Portland experiences a humid continental climate. Summers are typically warm, averaging 79°F (26°C), while winters, known for their snowfall, can drop to 12°F (-11°C). Autumn is colorful with fall foliage, and spring brings mild and refreshing weather.
What are some of the best things to do in Portland?
There's a wealth of activities to enjoy in Portland. Visitors often explore the historic Old Port district, sample local produce at the Portland Farmers' Market, or take a Casco Bay Lines Ferry to the nearby islands. Visiting the Portland Museum of Art is also frequently recommended.
What is the best time of year to visit Portland?
The most popular time to visit Portland is during the summer, from June to August. This period features warm weather and several local events, including the Old Port Festival in June and the Maine Lobster Festival in nearby Rockland in August.
What are the best places to stay in Portland?
Portland, Maine, has numerous charming neighborhoods, each with a unique character. The Arts District is known for its creative buzz and art galleries, while the Old Port area boasts cobblestone streets and waterfront views. Peaks Island, just a 20-minute ferry ride from downtown, provides a serene, coastal stay.
What are the best places to visit in Portland?
Visitors to Portland often find delight in exploring the Portland Museum of Art, the historic Victoria Mansion, and the Eastern Promenade park. A trip to the iconic Portland Head Light, one of the oldest functioning lighthouses in the US, is also frequently suggested.
What are some hiking trails in Portland?
For nature enthusiasts, Portland has several hiking trails. The Fore River Sanctuary Trail provides picturesque views and a chance to spot local wildlife, while the Back Cove Trail offers an easy urban hike around a tidal basin. The Peaks Island Loop is another scenic coastal trail.
What are some family activities to do in Portland?
Families visiting Portland can enjoy a fun-filled day at the Children's Museum and Theatre of Maine, explore the fascinating sea life at the Maine State Aquarium, or take a scenic ferry ride to Peaks Island. A stroll in the Eastern Promenade park is also a popular choice.
What are some of the best day trip ideas in Portland?
From Portland, visitors often take day trips to the coastal town of Kennebunkport, the scenic Peaks Island, or Freeport for shopping at the famed L.L. Bean flagship store. The stunning Acadia National Park, though a bit farther at 160 km, is a popular choice for a longer day trip.
What types of vacation rentals are available in Portland?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Portland. From over 110 condo rentals to over 370 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Portland?
Yes! Work meets play with ease at over 750 vacation rentals in Portland featuring dedicated workspaces. Stay connected and productive in your home away from home.
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