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.

Superhost

Apartment in Portland

4.82 out of 5 average rating, 347 reviews

Spacious and Comfortable Private Apartment

Third floor (i.e. a few stairs) spacious apartment with a private entrance. Walking distance to Thompson’s Point, Maine Med and many other trails and attractions. The Old Port is a 5 minute drive (1.5 mi.). There is plenty of free street parking available. Space heaters warm the space in the winter, and a/c is provided in the summer. The house is shared by first floor tenants while our family occupies the second floor. Again, several stairs to navigate, but quite comfortable once you settle in!

Mar 9 – 16

ﺩ.ﺇ240 per night
Superhost

Apartment in Portland

4.88 out of 5 average rating, 374 reviews

Modern East End studio, perfect Portland home base

Enjoy all that Portland has to offer from this clean, modern, and spacious studio in the city's hippest neighborhood. Walk one block to enjoy Duckfat frites at the Oxbow beer garden or head down Washington Ave to sample the best restaurants in Portland including Drifter's Wife, Cong Tu Bot, and Izakaya Minato, among others. Walk 5 mins up Munjoy Hill to picnic on the Eastern Promenade overlooking Casco Bay or 10 mins down into the Old Port. Do it all from this beautiful and private apartment!

Nov 27 – Dec 4

ﺩ.ﺇ441 per night
Guest favorite

Guesthouse in Portland

4.95 out of 5 average rating, 278 reviews

Beautiful large studio on the ocean.

Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

Apr 25 – 30

ﺩ.ﺇ592 per night

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
Allagash Brewing Company156 locals recommend

Portland beach vacation rentals

Guest favorite

Apartment in Portland

4.82 out of 5 average rating, 191 reviews

Beachy 1BR Atop Munjoy Hill+Steps to Eastern Prom

Nov 29 – Dec 6

ﺩ.ﺇ570 per night
Guest favorite

Apartment in Portland

4.97 out of 5 average rating, 219 reviews

"Percival" Penthouse Suite - Amazing Harbor Views

Nov 12 – 19

ﺩ.ﺇ1,732 per night
Guest favorite

Guest suite in Portland

4.95 out of 5 average rating, 150 reviews

Joyful Munjoy Hill Garden Suite

ﺩ.ﺇ327 per night
Superhost

Apartment in Scarborough

4.85 out of 5 average rating, 433 reviews

Tiny Pine Point Beach Pad - comfy, cozy surf shed

Apr 13 – 20

ﺩ.ﺇ390 per night
Guest favorite

Cottage in Scarborough

4.97 out of 5 average rating, 161 reviews

Bright, clean, private cottage near Higgins Beach!

Feb 22 – Mar 1

ﺩ.ﺇ578 per night
Guest favorite

Apartment in Portland

4.9 out of 5 average rating, 378 reviews

Private Hill Top Apartment Two/On Street Parking

Apr 11 – 18

ﺩ.ﺇ500 per night
Superhost

Apartment in Portland

4.88 out of 5 average rating, 377 reviews

Updated stylish 1 BR Downtown Apt

Nov 16 – 23

ﺩ.ﺇ584 per night
Superhost

Apartment in Portland

4.82 out of 5 average rating, 310 reviews

Charming roomy in-town apartment, parking included

Apr 24 – May 1

ﺩ.ﺇ492 per night
Guest favorite

Guest suite in South Portland

5.0 out of 5 average rating, 675 reviews

Oceanfront with amazing views and private entrance

Sep 15 – 22

ﺩ.ﺇ1,188 per night
Guest favorite

Apartment in Portland

4.97 out of 5 average rating, 372 reviews

RETRO BnB in the Heart of East End Portland

May 27 – Jun 3

ﺩ.ﺇ709 per night
Superhost

Apartment in Portland

4.85 out of 5 average rating, 157 reviews

Lovely studio in downtown Portland

Jan 2 – 9

ﺩ.ﺇ592 per night
Guest favorite

Apartment in Portland

4.99 out of 5 average rating, 611 reviews

Old Port / Parking / Patio

Apr 21 – 28

ﺩ.ﺇ782 per night

Private Portland vacation rentals

Guest favorite

Guest suite in Portland

4.95 out of 5 average rating, 108 reviews

Sunflower Retreat in North Back Cove

Sep 9 – 16

ﺩ.ﺇ548 per night
Guest favorite

Apartment in Portland

4.85 out of 5 average rating, 437 reviews

Cozy, Private Apartment

Nov 11 – 18

ﺩ.ﺇ437 per night
Guest favorite

Guest suite in Freeport

4.96 out of 5 average rating, 114 reviews

Solar Suite surrounded by Nature

Nov 23 – 30

ﺩ.ﺇ448 per night
Guest favorite

Cabin in Lovell

4.98 out of 5 average rating, 246 reviews

Secluded, cozy cabin nestled in the Maine woods

Sep 13 – 20

ﺩ.ﺇ417 per night
Guest favorite

Loft in South Portland

5.0 out of 5 average rating, 105 reviews

Serene studio apartment, close to everything.

Apr 21 – 26

ﺩ.ﺇ507 per night
Guest favorite

Cottage in Scarborough

4.85 out of 5 average rating, 279 reviews

Charming beach cottage

Apr 22 – 29

ﺩ.ﺇ412 per night
Guest favorite

Apartment in Gorham

4.96 out of 5 average rating, 194 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Apr 17 – 24

ﺩ.ﺇ418 per night
Guest favorite

Apartment in Arundel

4.91 out of 5 average rating, 125 reviews

Ginger Hilltop

Mar 4 – 11

ﺩ.ﺇ396 per night
Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 214 reviews

Cottage on Black Brook Preserve

May 30 – Jun 6

ﺩ.ﺇ465 per night
Guest favorite

Apartment in Portland

4.93 out of 5 average rating, 595 reviews

Extraordinary Architectural Masterpiece Downtown

Feb 20 – 27

ﺩ.ﺇ1,160 per night
Guest favorite

Apartment in Portland

4.99 out of 5 average rating, 300 reviews

Quiet West End Retreat - parking - 100% Non Smoker

Oct 5 – 12

ﺩ.ﺇ656 per night
Guest favorite

Guest suite in Scarborough

4.98 out of 5 average rating, 138 reviews

Beautiful, private apartment!! Great location!

Nov 4 – 11

ﺩ.ﺇ483 per night

Portland house rentals

Superhost

Home in Falmouth

4.86 out of 5 average rating, 173 reviews

Amazing Bay View Home with Hot Tub

Feb 17 – 24

ﺩ.ﺇ489 per night
Guest favorite

Home in Lebanon

4.96 out of 5 average rating, 158 reviews

Tranquility, Relaxation, Family, Romance

Oct 22 – 29

ﺩ.ﺇ440 per night
Guest favorite

Home in Portland

4.96 out of 5 average rating, 128 reviews

Quiet Comfy Victorian Escape

Dec 15 – 22

ﺩ.ﺇ810 per night
Guest favorite

Home in Portland

4.88 out of 5 average rating, 242 reviews

Perfectly Portland

Apr 16 – 23

ﺩ.ﺇ694 per night
Guest favorite

Home in Hollis

4.98 out of 5 average rating, 353 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Aug 27 – Sep 3

ﺩ.ﺇ671 per night
Guest favorite

Home in Edgecomb

4.95 out of 5 average rating, 397 reviews

Sheepscot Harbour Cottage/waterview

Feb 15 – 22

ﺩ.ﺇ496 per night
Guest favorite

Home in Biddeford

4.97 out of 5 average rating, 379 reviews

Private, spacious, colorful, fun & unique space

Nov 20 – 27

ﺩ.ﺇ361 per night
Guest favorite

Home in Lewiston

4.98 out of 5 average rating, 133 reviews

Clean and comfortable home

Apr 30 – May 7

ﺩ.ﺇ412 per night
Guest favorite

Home in Portland

4.98 out of 5 average rating, 308 reviews

3 bedroom house in the heart of Portland

Nov 3 – 10

ﺩ.ﺇ1,796 per night
Guest favorite

Home in Edgecomb

4.99 out of 5 average rating, 117 reviews

Cozy Lodge Meets Mid Century Hideaway

Apr 22 – 29

ﺩ.ﺇ666 per night
Guest favorite

Home in Acton

4.98 out of 5 average rating, 117 reviews

The ZEN welcomes you, your home away from home.

Aug 22 – 29

ﺩ.ﺇ834 per night
Guest favorite

Home in Oxford

5.0 out of 5 average rating, 178 reviews

The Modern Lakehouse

Nov 22 – 29

ﺩ.ﺇ2,110 per night

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 1,410 vacation rentals in Downtown Portland, over 1,410 vacation rentals in Waterfront District, and over 1,040 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 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

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Portland