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.
Vacation rentals for every style
Get the amount of space that is right for you
Portland beach vacation rentals
Private Portland vacation rentals
Portland house rentals
Quick stats about vacation rentals in Portland
Rentals with dedicated workspaces
|720 properties have a dedicated workspace|
Rentals with a pool
|40 properties have a pool|
|350 properties allow pets|
|760 properties are a good fit for families|
Total number of reviews
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
Where should I stay in Portland?
Make yourself at home in Portland by choosing from our most frequently booked neighborhoods. We have over 1,380 vacation rentals in Downtown Portland, over 1,380 vacation rentals in Waterfront District, and over 1,030 vacation rentals in Peaks Island.
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 360 house rentals to over 110 condo 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 720 vacation rentals in Portland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Portland?
Four-legged friends are welcome in Portland. Choose from more than 350 vacation rentals for guests traveling with pets.
Are there Portland vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Portland, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in condo rentals in Portland?
Experience the best of Portland with our condo rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Portland have a bbq area?
Absolutely! We offer over 170 house rentals with a bbq area in Portland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Portland have self check-in?
Absolutely! We offer over 170 house rentals with self check-in in Portland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Portland have a gym?
Absolutely! We offer over 30 house rentals with a gym in Portland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Portland?
Portland has more than 270 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.