Portland vacation rentals

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Popular amenities for Portland vacation rentals

Stay near Portland's top sights

Peaks Island176 locals recommend
The Maine Mall86 locals recommend
Portland International Jetport50 locals recommend
Fort Williams Park229 locals recommend
Portland Observatory132 locals recommend
Allagash Brewing Company156 locals recommend

Portland beach vacation rentals

Guest favorite
Apartment in Portland
Hip & Cozy, high end Modern Design
Nov 13 – 20
$123 per night
4.9 out of 5 average rating, 341 reviews
Guest favorite
Guesthouse in Portland
Beautiful large studio on the ocean.
Apr 28 – May 5
$134 per night
4.95 out of 5 average rating, 277 reviews
Guest favorite
Cottage in Scarborough
Bright, clean, private cottage near Higgins Beach!
Sep 22 – 29
$135 per night
4.97 out of 5 average rating, 161 reviews
Guest favorite
Apartment in Portland
Modern East End studio, perfect Portland home base
Nov 1 – 8
$109 per night
4.88 out of 5 average rating, 373 reviews
Guest favorite
Apartment in Portland
Clean East Bayside Apartment- Amazing Location!!
Apr 26 – May 3
$95 per night
4.81 out of 5 average rating, 188 reviews
Guest favorite
Guest suite in Portland
Joyful Munjoy Hill Garden Suite
$88 per night
4.95 out of 5 average rating, 150 reviews
Superhost
Apartment in Portland
Downtown Portland 1 Bedroom
Apr 15 – 22
$114 per night
4.86 out of 5 average rating, 130 reviews
Guest favorite
Apartment in Portland
"Percival" Penthouse Suite - Amazing Harbor Views
Oct 1 – 8
$750 per night
4.97 out of 5 average rating, 219 reviews

Private Portland vacation rentals

Guest favorite
Guest suite in Freeport
Solar Suite surrounded by Nature
Jul 15 – 22
$106 per night
4.96 out of 5 average rating, 114 reviews
Guest favorite
Cabin in Lovell
Secluded, cozy cabin nestled in the Maine woods
Oct 27 – Nov 3
$99 per night
4.98 out of 5 average rating, 246 reviews
Guest favorite
Guest suite in Freeport
Weather's Edge, Freeport
Jun 30 – Jul 7
$83 per night
4.96 out of 5 average rating, 193 reviews
Guest favorite
Apartment in Portland
Compact & Complete in residential neighborhood
Oct 9 – 16
$136 per night
4.96 out of 5 average rating, 148 reviews
Guest favorite
Apartment in Portland
Quiet West End Retreat - parking - 100% Non Smoker
Sep 29 – Oct 6
$153 per night
4.99 out of 5 average rating, 300 reviews
Guest favorite
Home in Lisbon
Unplug at a Beachy Bolthole with Classic New England Style
Jan 22 – 29
$57 per night
4.94 out of 5 average rating, 326 reviews
Guest favorite
Tiny home in Portland
The Garden Cabin Tiny Home
May 19 – 26
$129 per night
4.97 out of 5 average rating, 397 reviews
Guest favorite
Guest suite in Scarborough
Beautiful, private apartment!! Great location!
Nov 28 – Dec 5
$117 per night
4.98 out of 5 average rating, 138 reviews

Portland house rentals

Guest favorite
Home in Portland
Quiet Comfy Victorian Escape
Nov 13 – 20
$192 per night
4.96 out of 5 average rating, 128 reviews
Guest favorite
Home in Westbrook
Reno Barn w/ a lot of Charm! Breweries & Airport
Jan 8 – 15
$163 per night
4.88 out of 5 average rating, 439 reviews
Guest favorite
Home in Biddeford
Private, spacious, colorful, fun & unique space
Oct 20 – 27
$89 per night
4.97 out of 5 average rating, 378 reviews
Guest favorite
Home in Hollis
Birch Ledge Guesthouse--Four Season Maine Getaway
Sep 7 – 14
$160 per night
4.98 out of 5 average rating, 352 reviews
Guest favorite
Home in Portland
Perfectly Portland
Apr 17 – 24
$164 per night
4.88 out of 5 average rating, 242 reviews
Guest favorite
Home in Lebanon
Tranquility, Relaxation, Family, Romance
Oct 25 – Nov 1
$105 per night
4.96 out of 5 average rating, 156 reviews
Guest favorite
Home in Acton
The ZEN welcomes you, your home away from home.
Jun 6 – 13
$183 per night
4.98 out of 5 average rating, 116 reviews
Guest favorite
Home in Portland
3 bedroom house in the heart of Portland
Feb 4 – 11
$429 per night
4.98 out of 5 average rating, 309 reviews

Quick stats about vacation rentals in Portland

Total rentals

1.5K properties

Rentals with dedicated workspaces

770 properties have a dedicated workspace

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

390 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 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.

  • Where should I stay in Portland?

    Make yourself at home in Portland by choosing from our most frequently booked neighborhoods. We have over 1,040 vacation rentals in Peaks Island, over 1,410 vacation rentals in Waterfront District, and over 1,410 vacation rentals in Downtown Portland.

  • 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 120 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 770 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 390 vacation rentals for guests traveling with pets.

Destinations to explore

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