
Vacation rentals in Portland
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Top-rated vacation rentals in Portland
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Private vacation rentals in Portland

2BR w/ Deck & Parking | 5 Min to Downtown
Cannot recommend Danni's place enough - super-cute and has everything you need! We loved it and would return in a heartbeat! One caveat as noted in other reviews (which we didn't initially see) - but there is a family living upstairs with young children, and while the walls are soundproofed well (we heard no conversation or crying for the most part) the pitter-patter of little feet at 5:30am was an earlier wake-up than we expected ;) So you will hear running around and thuds at toddler-active times, but we mostly laughed it off and it was a good reminder of how glad we are not to be at that stage of life anymore! Don't let it dissuade you from booking - great place for the price.

Cityscape Loft. Central Location
Great, spacious place, central location. Incredibly clean and AC was already on when we arrived which was so nice for the hot weather. Chris was great.

Cape Elizabeth Garden Apt+Beach+Close to Portland!
Beautiful location just outside of Portland. Host was very nice and communicative, would recommend staying there!

Portland Back Cove Hideaway-1 BR- With Patio
The air bnb was very cozy and cute, just like the pictures. Great location, close to a lot of restaurants and attractions. The host was very attentive and communicative. Only thing was that the hot/cold water takes a while to get to the range you want it to in the shower but everything else was superb! Would definitely recommend and stay again!

Sauna & fire table near Portland's Back Cove
We had a great stay. The location is quiet but just a few minutes away from amazing restaurants, cafes, and breweries. Highlights: The bed was super comfortable. The sauna was great on a rainy day. The walkability to the Back Bay trail was appreciated.

Renovated 1 BR Downtown Apt w/backyard
We had a wonderful stay in Portland. The space was clean, easy to get to, with ample street parking. It was walkable to many restaurants and bars. We would stay here again!

Hidden Garden Apartment in Portlands West End
Alex was very communicative and the location is perfect for easy access to downtown Portland. The space was quiet and private. The designated parking spot is also a great perk given how much of a hassle it can be to park in downtown Portland. Definitely recommend staying here!

Urban Jewel Box on Munjoy Hill
We really enjoyed our stay here. The apartment is in a perfect location, only a few minutes walk from great coffee shops and restaurants. The apartment is well equipped and stylishly decorated.
House rentals in Portland

Quiet Comfy Victorian Escape
This is really for someone who appreciate small details of the place(decor and so on). Within walking distance to basic necessities. Reasonable Uber fares to all places(Airport, Train Station, Old Port, Maine Mall).

Reno Barn w/ a lot of Charm! Breweries & Airport
We had a great stay at Diane and Joe’s place—it was exactly as described and exceptionally clean. We decided to arrive a day early, and Diane was kind enough to accommodate us without hesitation. She was consistently responsive and pleasant throughout our stay. The Reno Barn itself is charming and comfortable. We especially enjoyed relaxing on the back deck, which has cozy seating and an umbrella for shade—a perfect spot to unwind. While the spiral staircase to the loft and second bedroom might be a bit tricky for some, it wasn’t an issue for us. The master bedroom on the lower level was very comfortable, and we appreciated the generous supply of sheets, towels, and blankets. While the location isn’t walkable, it offers easy access to both downtown Portland and the airport, each just a 15-minute drive away. Overall, we had a wonderful experience and would absolutely recommend this place to others. We’d be happy to stay here again the next time we’re in the Portland area.

Waterfront Gem walkable to Restaurants!
It’s very cute little house. We’re enjoy it. Thank you so much.

East End Unit
My wife, myself and our pup loved our time at Christine’s. Thought it was a great value for the area and we appreciated how many little extras were included (snacks, beer, wine, seltzer, toiletries). Location is great for walks to East Prom or Old Port, and parking is a breeze with the dedicated driveway. It is a cozy fit if you’re a bigger person (I’m 6’ and I had just a few inches of clearance from the ceiling).

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
We had a wonderful stay in Angela’s beautiful home. It had great amenities, was super clean, and had everything we needed. Loved the pool and fire pit. The kitchen was roomy for cooking too. 5 stars!

Beautiful Coastal Maine Getaway
We loved our time staying here, the house was beautiful and just as described/ seen in the pictures. Randy was a great host and always very responsive with some great local recommendations. Would definitely love to return!

Stunning Ocean Views From This Peaks Island Home
Such a great little spot in one of the nicest corners of Peaks Island! John was great, being flexible with me when my arrival time needed to be changed up. Would visit again and again!

Amazing Bay View Home with Hot Tub
What a cozy retreat!! Perfect for our family of 4. The decor was adorable, the home was spotless, the view was lovely, and the hot tub was the perfect bonus. Our family appreciated the extra effort put in to providing local maps and recommendations! We can’t wait to return and explore even more.
Condo rentals in Portland

Luxury Beach Front Condo! Prime Location!
Wonderful place, beautiful view, clean home, would Definitely rebooked in the near future! 100% recommend

Old Port on foot
Great place .. perfect location . I wish I had read further about the parking. $130 total to park for two days. Outside of that all good. Needed to know where the trash key was, and needed an extra trash bag, but they were very responsive .

Oceanfront Condo with Awesome Views
I would recommend it 100%

Modern Industrial Beach Cottage
cute and clean place! thanks.

Cozy condo by the beach!
Such a cozy place! I was on a trip alone and I felt so comfortable and safe. Definitely a place I’m booking next time I’m back in Maine.

Portland 1 Bedroom Condo in the Arts District.
The condo was perfect! Very clean, neat, cute decor. I loved the box of dog supplies that the host left. The condo was also in a GREAT area, walkable to bars, restaurants, coffee shops, stores. The host, Jason was friendly and accommodating. I will definitely return to Portland and stay in this condo again.

Comfy condo with loft by the beach!
This was a teeny tiny condo (<200 sq ft!) but spotlessly clean, well appropriated, and a great location. The bed was comfy and the loft area was tall enough to sit up and move around. It was a 5 minute walk to Pine Point Beach. There are about dozen other tiny cottages in the condo association, clustered around a central parking lot, so if all of them were full there wouldn’t be a ton of privacy but we were there in the off season and it was peaceful and quiet.

Mary J. Eastburn House--Baxter Suite
The Baxter Suite was perfect for our weekend stay with 4 people. Thomas was a great host- very responsive and accommodating. The apartment is beautiful and very clean. The bathroom is gorgeous and beds were so comfy. One note is that the only mirror is in the bathroom and there is no full length mirror (not a huge issue but a small struggle with 4 women trying to get ready at the same time lol). The free parking spot was very nice to have but there was also plenty of street parking available. Overall Thomas’s place had everything we needed and we would stay here again!
Quick stats about vacation rentals in Portland
Total rentals
1.6K properties
Total number of reviews
172K reviews
Family-friendly rentals
850 properties are a good fit for families
Pet-friendly rentals
450 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
800 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 430 house rentals to over 100 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 800 vacation rentals in Portland featuring dedicated workspaces. Stay connected and productive in your home away from home.
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- Ogunquit Beach
- Wells Beach
- Sebago Lake
- Scarborough Beach
- York Harbor Beach
- Long Beach
- Surfside Beach
- Popham Beach State Park
- Long Sands Beach
- Fox Ridge Golf Club
- Cranmore Mountain Resort
- Wentworth by the Sea Country Club
- Pemaquid Beach
- Brunswick Golf Club
- East End Beach
- Palace Playland
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Purity Spring Resort
- King Pine Ski Area
- Parsons Beach
- Ogunquit Playhouse
- Ferry Beach
- Cliff House Beach
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