Portland vacation rentals

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Popular amenities for Portland vacation rentals

Stay near Portland's top sights

The Maine Mall86 locals recommend
Peaks Island176 locals recommend
Portland International Jetport50 locals recommend
Fort Williams Park229 locals recommend
Portland Observatory132 locals recommend
Thompson Point28 locals recommend

Other great vacation rentals in Portland

Guest favorite

Apartment in Portland

4.92 out of 5 average rating, 109 reviews

Heart of East End/Munjoy Hill- quiet and central!

Jan 6 – 13

G$31,949 GYD per night
Guest favorite

Apartment in Portland

4.91 out of 5 average rating, 289 reviews

Small cozy downtown loft

Jan 3 – 10

G$29,846 GYD per night
Guest favorite

Apartment in Portland

4.91 out of 5 average rating, 349 reviews

Hip & Cozy, high end Modern Design

Jan 9 – 16

G$30,073 GYD per night
Guest favorite

Apartment in South Portland

4.91 out of 5 average rating, 149 reviews

Sunny and beautiful brick house apartment

Nov 8 – 15

G$32,035 GYD per night
Guest favorite

Guest suite in Portland

4.97 out of 5 average rating, 574 reviews

PRlVATE SUlTE in the Heart of East End Portland

Oct 15 – 22

G$39,136 GYD per night
Guest favorite

Guest suite in Saco

4.94 out of 5 average rating, 382 reviews

Barn-Board Abode (private studio) powered by solar

Sep 25 – Oct 2

G$28,297 GYD per night
Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 431 reviews

Harpswell Studio on Waterview Property! Lobster!

May 10 – 17

G$28,280 GYD per night
Guest favorite

Apartment in Portland

4.97 out of 5 average rating, 229 reviews

"Percival" Penthouse Suite - Amazing Harbor Views

Jan 2 – 9

G$77,119 GYD per night

Private Portland vacation rentals

Guest favorite

Home in Lisbon

4.94 out of 5 average rating, 335 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Jan 21 – 28

G$14,420 GYD per night
Guest favorite

Guest suite in Cumberland

4.92 out of 5 average rating, 108 reviews

Springer Park! adorable guesthouse very stylish!

Sep 2 – 9

G$27,628 GYD per night
Guest favorite

Cabin in Lovell

4.97 out of 5 average rating, 258 reviews

Secluded, cozy cabin nestled in the Maine woods

Sep 13 – 20

G$23,706 GYD per night
Superhost

Apartment in Portland

4.89 out of 5 average rating, 271 reviews

Quaint West End Flat, 1 bedroom, lots of character

Oct 25 – Nov 1

G$28,339 GYD per night
Guest favorite

Apartment in Freeport

5.0 out of 5 average rating, 130 reviews

Cozy Maine Barn Hideaway- 2nd Floor Apartment

May 25 – Jun 1

G$33,684 GYD per night
Guest favorite

Apartment in Portland

4.85 out of 5 average rating, 439 reviews

Cozy, Private Apartment

Nov 11 – 18

G$25,778 GYD per night
Guest favorite

Apartment in Boothbay

4.96 out of 5 average rating, 260 reviews

Sunnymeade

Nov 8 – 15

G$13,915 GYD per night
Guest favorite

Loft in South Portland

5.0 out of 5 average rating, 109 reviews

Serene studio apartment, close to everything.

Apr 26 – May 3

G$33,377 GYD per night

Portland house rentals

Guest favorite

Home in Portland

4.95 out of 5 average rating, 292 reviews

Explore Portland from a 18th-Century Victorian

Nov 3 – 10

G$36,456 GYD per night
Guest favorite

Home in Freeport

4.99 out of 5 average rating, 163 reviews

"The Cozy Cottage in the heart of Freeport Village

Feb 7 – 14

G$28,863 GYD per night
Guest favorite

Home in Westbrook

4.88 out of 5 average rating, 446 reviews

Reno Barn w/ a lot of Charm! Breweries & Airport

Oct 31 – Nov 7

G$34,085 GYD per night
Guest favorite

Home in Portland

4.96 out of 5 average rating, 128 reviews

Quiet Comfy Victorian Escape

Dec 18 – 25

G$45,971 GYD per night
Guest favorite

Home in Gorham

4.99 out of 5 average rating, 138 reviews

Beautiful Home In Gorham Maine

Jan 2 – 9

G$36,557 GYD per night
Guest favorite

Home in Lewiston

4.98 out of 5 average rating, 140 reviews

Clean and comfortable home

Jun 9 – 16

G$23,520 GYD per night
Guest favorite

Home in Freeport

4.85 out of 5 average rating, 249 reviews

Home On Pond in Woods - Guest Suite

Oct 6 – 13

G$17,759 GYD per night
Guest favorite

Home in Lebanon

4.96 out of 5 average rating, 164 reviews

Tranquility, Relaxation, Family, Romance

Apr 12 – 19

G$24,986 GYD per night

Quick stats about vacation rentals in Portland

  • Total rentals

    1.5K properties

  • Rentals with dedicated workspaces

    780 properties have a dedicated workspace

  • Rentals with a pool

    70 properties have a pool

  • Pet-friendly rentals

    400 properties allow pets

  • Family-friendly rentals

    780 properties are a good fit for families

  • Total number of reviews

    151K 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

  • 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 360 house rentals to over 120 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 780 vacation rentals in Portland featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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