Skydiving – 15 Best Airbnbs in Portland, ME (2023 Edition)

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Maine, in the far northeast corner of the United States, has dense evergreen forests and mountains that brush up against the Atlantic Ocean. Here, thriving port cities bring the bounty of the ocean to lucky restaurants and their guests. It’s no secret Mainers know good seafood, but the city of Portland is also known for plenty of other things, from views of the working docks to trendy neighborhoods with stately Victorian homes and lively shopping streets. Nature enthusiasts can also escape the city by sailboat for a hike on the Casco Islands.

Your vacation can be made all the more enjoyable by booking a wonderful apartment or condo through Airbnb. We’ve compiled a list of the best Airbnbs in Portland, Maine, to get your search started. All of these Airbnbs are run by superhosts – hosts with a proven track record of quality service. In addition, some of the rentals have been designated Airbnb Plus, meaning that they have been carefully vetted by in-person inspections to ensure that guests receive the highest quality services.

Related: 15 Best Airbnbs in Maine, USA

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West End Guest Suite

Enjoy views of the harbor through the wide windows of this two-story guest suite hosted by Aimee in the historic neighborhood of West End. Nearby working docks remind guests that Portland is a port city, complete with ferries, fishing boats, and the freshest seafood.

Two guests can share the bedroom with its queen-size bed and full bathroom. The spacious kitchenette downstairs has a minifridge, toaster oven, and hot plate. Minimally decorated on the inside, the space has windows in every room that draw your gaze to the beautiful surrounding landscape of the home. There’s a pool on the premises that is open seasonally. From there, you can also watch boats come in and out of the harbor.

This Airbnb Plus puts you within walking distance of Old Port, a revitalized warehouse district by the waterfront. In the other direction is the Arts District, where you can find museums and theaters. From the suite, Portland International Jetport is under 15 minutes by car. With so much great activity and excitement around, this Airbnb in Portland makes a great place to stay.

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Turn-of-the-Century Barn

Superhosts Kathryn and Rick have renovated this barn in an urban garden and turned it into one of the best Airbnbs in Portland, Maine, for solo travelers and couples. An eclectic collection of furniture is balanced by clean white walls throughout. With a private entrance and free, off-street parking, the self check-in process is convenient any time after 3 p.m.

A queen-size bed in the room upstairs and pull-out sofa in the living room guarantee that up to two guests will have plenty of space and privacy. A reading nook is tucked into a corner upstairs with a plush armchair and side table. The full kitchen is available for guests to do their own cooking, and you can have your meals in either the breakfast nook or at the dining room table.

The urban neighborhood is great for pedestrians. You can admire the Victorian architecture of homes on a walk to the Arts District for live entertainment or to Old Port for dinner at an ocean-to-table restaurant. The nearby Western Promenade, or Prom, is a historic public park and recreation area developed in the early 20th century.

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Eclectic Urban Studio

A studio apartment is an efficient solution for vacationers who want more space than a conventional room for rent affords. This rental offers a queen-size bed around the corner from a bright living room with a couch and TV, while the full kitchen with dishwasher has plenty of cooking space. The layout and amenities make it very comfortable for short-term stays for up to two guests.

The Portland Observatory, which opened in 1807, is in the neighborhood. It is now the last maritime tower of its kind in the United States. A short walk east will bring you to East End Beach, where paddle boards and kayaks can be rented. A ferry terminal to the south can take you out to Great Diamond Island.

As vacation rentals in Portland go, this studio is an easy and comfortable choice in a good location for travelers who want to see a port city in its prime.

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18th-Century Victorian Home

Looking like a storybook setting, this idyllic Victorian home is a great rental for family vacations with its capacity for up to four guests. White walls and mostly white décor and furniture throughout create an airy sense of space. 

The home has many features to make your stay comfortable. The single bedroom with a king-size bed is supplemented by a couch in the living room for extra sleeping space; children and young travelers are welcome. The kitchen is compact but fully equipped to serve your needs. The bathroom has a soaking tub where you can unwind. And, finally, there is a free parking space on the premises.

In the neighborhood are restaurants like The Treehouse and Woodford Food and Beverage for nights out. You can visit Baxter Woods a few blocks to the north to enjoy the Portland weather. 

Make your trip an adventure without sacrificing comfort by staying in this Portland Airbnb Plus.

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Two-Bedroom Apartment

If you and your traveling companions prefer to retreat to your own space at the end of the day, you will love this Airbnb Plus hosted by Alice. The apartment has two bedrooms, one with a full-size bed, the other with a queen-size bed. Just off the full kitchen is a shared bathroom that has a claw-foot tub and periwinkle walls. You and up to three more guests can also hang together on the plush leather sofa in the living room or on the front porch with its café-style table and chairs.

A few blocks from the apartment is Baxter Boulevard, a popular place for locals to stroll and walk dogs, which is great because your four-legged family member is very welcome to join you at this apartment in Portland. More popular still are the diverse restaurants throughout Greater Portland, which have earned it the title America’s Foodiest Small Town by Bon Appétit magazine.

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Historic Home with Modern Décor

Travel with style in this luxuriously appointed apartment where five guests can share the two bedrooms with queen-size beds. Nine-foot cathedral ceilings and original hardwood floors are just the beginning of this Airbnb Plus in Portland. The house’s historic architecture is balanced by sleek, contemporary furniture in dramatic contrasting colors. Original brick peeks through in the full kitchen and bathroom, adding texture and color. 

The interior design of this rental alone is enough to make it one of the best Portland Airbnbs, but the location in the beautiful West End neighborhood is also amazing. This apartment puts travelers close to the Victorian Mansion Museum and Portland Museum of Art. A short walk to Congress Street will reward you with a string of restaurants, each influenced by a different ethnic cuisine.

Being so close to Old Port’s range of shopping and entertainment, you won’t run out of things to do on your trip. Sample the Portland craft brews before the end of your vacation by walking the coastal section of the Maine Beer Trail, which connects over 100 craft breweries.

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Loft in East End

At the easternmost tip of the peninsula that Portland sits on, you’ll find a perfect studio loft for as many as four travelers looking to explore Maine. The Casco Bay Islands are prime territory for renting kayaks and paddle boards or letting someone else guide your tour on a schooner. Day hiking the islands is an easy and convenient way to discover Maine’s beautiful scenery.

The apartment itself has two areas for sleeping: one on the same level as the living space, the other up in the loft area, both sporting queen-size mattresses. Though compact, the kitchen comes equipped with everything you need if you can resist the allure of the many East End restaurants. The shared bathroom has a walk-in shower and is tiled with various brown hues.

Not surprisingly, given host Susan’s status as editor-in-chief of a décor magazine, the loft is perfectly decorated without being crowded by knickknacks. Glowing reviews have rated this stay as an almost perfect 5-star Portland Airbnb.

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Eccentric One-Bedroom Apartment

Open for short- or long-term stays, this apartment is a simple but comfortable place for two guests. The workspace with fast Wi-Fi is ideal for those traveling on business. The kitchen is stocked with necessities, and there is a laundromat around the corner. In the bedroom, a bay window provides a lovely street view from the queen-size bed. The hardwood floors are covered with a variety of textiles in bold prints, creating a unique look.

The best part of this Airbnb in Portland, Maine, is the location, specifically how close it is to a diverse range of restaurants. From the heart of the West End residential neighborhood, it’s a short walk to Congress Street, which is loaded with options, from food trucks to fine dining and everything in between. Portland was Bon Appétit magazine’s 2018 Best Restaurant City of the Year, and its restaurant owners are still creating incredible dining experiences for visitors every day.

Whether you’re primarily drawn to the proximity of this apartment to some of Portland’s best dining opportunities or to the quiet residential streets that are perfect for a restful escape, this Portland Airbnb will make a great rental for your Maine getaway.

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Bright Modern Old Port Rental

Portland has a lot to offer, and it’s going to take more than a weekend to see it all. This Airbnb in downtown Portland, Maine, will make a fantastic long-term home for a solo traveler or couple. The private entrance and parking on the premises make it easy to feel right at home.

The décor channels the nautical theme of the town. In the bedroom is a queen-size bed and a closet. There is a washer-dryer unit in the apartment, and the bathroom is stocked up on all the necessities. The incredibly spacious kitchen with an island doubles as a great place to eat your meals.

There is a shared courtyard space in the back yard with a garden, two gas grills you can use if they aren’t otherwise occupied, and several covered tables with chairs for outdoor dining. Between the amenities on-site and the apartment’s proximity to all that neighborhoods like Old Port and Bayside have to offer, it’s easy to see why this location is one of the best Airbnb rentals in Portland.

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Sophisticated Charm

Light and lovely, this Airbnb for up to four guests represents everything great about renting a house in Portland. Light-colored walls and textiles help the space feel bigger, and plush sofas and chairs make it inviting.

There are two bedrooms in the Airbnb, one with a king-size bed and the other with a queen. The shared bathroom has a tub as well as a washer and dryer. The lauded Rosemont Market and Bakery will keep your kitchen stocked with goodies. You can use the grill in the backyard, and between that and the full kitchen, you have all the comforts of home in this vacation house for rent in Portland.

By staying in the heart of West End, you put yourself in a great position to explore Portland in every direction. In nearby Old Port, you can pick up a ferry or schooner to take a tour of whale-feeding grounds around the Casco Islands. On Congress Street, you don’t have to choose between dinner or a show as there are plenty of both. 

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Studio with a Sense of History

As stately as it is comfortable, this studio apartment is decorated to accentuate its history. The Victorian architecture is complemented by rich textiles. The dramatic black fireplace, adorned with a gold screen, sits across from the queen-size bed. The fold-out couch becomes a double bed, so the apartment can accommodate three guests.

The bathroom has a unique feature – separate his-and-her bathrooms connected by a walk-through shower. The shared-but-private design allows privacy for couples or small groups while saving space.

The kitchenette is suitable only for breakfast, but that will hardly be a problem with so many amazing places in and around Portland where you can eat out. Local eateries include Boda, a Thai restaurant, and Tandem Coffee and Bakery, which serves breakfast and lunch. And after eating, you can end your nights in a new cocktail lounge or jazz club.

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Modern Apartment for Four

The modern design of this apartment can be seen in its clean, smart lines, simple colors, and minimal décor. This style elevates it from your standard rental and makes it feel more suave. Situated on the first floor of the building, this Airbnb in Portland is a great option for a family vacation in Maine. For stays over four days long, your hosts will make the washer and dryer in the basement available.

There’s plenty of sleeping space here, with a queen-size bed in the bedroom and a couch that folds out into a second queen-size bed. The kitchen is stocked with cooking basics, and the island doubles as a convenient place to have your meals or get some work done.

As apartment rentals in Portland go, this one is a wonderful marriage of conveniences in both location and amenities.

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Victorian near the Arts District

You won’t find short-term rentals in Portland with more space than this one. At a sprawling 1,100 square feet, this apartment has plenty of space for a traveling duo. In the bedroom is a queen-size bed between two bedside tables, a closet, and a chest of drawers. The bathroom has everything you’ll need, including soaps and extra towels. There’s a houseplant in every room and a front porch with table and chairs where you can enjoy morning coffee or tea.

Outside is a garden that can be seen from the windows. Host Michael has a long list of recommendations for places to walk, eat, and explore. Given how close the rental is to Old Port and all that that neighborhood offers, the variety is not surprising. He also keeps on hand a book of walking tours of Portland for guests to use. Or, before you go, why not check out this guidebook Michael made through Airbnb?

There is a full kitchen, but Michael asks any guests not to cook meat in the kitchen to avoid the lingering scent.

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Stately One-Bedroom Apartment

If you want a short-term rental in Portland that looks like a world-class hotel, this stately, remodeled Greek revival will suit your aesthetic sensibilities perfectly. Vaulted 11-foot ceilings, crown molding, and stained glass combine to create a gorgeous home for your Maine respite. It’s a haven for two, with one bedroom and one bathroom, a queen-size bed, a full kitchen, and a washer and dryer.

The private porch attached to the condo overlooks the backyard garden, which is full of flowers if you visit during the warmer months or beautifully blanketed in snow in winter. The architecture of the surrounding homes is similar in style and makes it a joy to walk to one of the nearby cafés in the morning.

The Arts District where this apartment sits is a growing area of interest in Portland. It earned its moniker for the plethora of museums and performance centers in the area, such as the Children’s Museum and Theater of Maine, the Portland Museum of Art, and the State Theater.

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Oakdale Apartment for Six

This two-bedroom, one-bath apartment in Oakdale can host up to six people. Each bedroom has a queen-size bed, and the living room has a couch and space for an air mattress.

The host lives next door and has a list of recommendations for guests seeking great food experiences nearby. A few blocks east is Baxter Boulevard, which winds along the edge of Black Cove. Old Port and the Arts District are within two miles and thus easily reached by foot or car. Plan to stay in this Portland Airbnb for the additional amenities, beautiful yard, and spacious interiors.

The hardwood floors running throughout the rental (except in the laminate-floor bathroom) are made cozier by the addition of area rugs in various sizes and shades of blue and gray. Ten-foot cathedral ceilings and bay windows open up the rooms so that your group will never feel cramped. There are two spots to park cars on the premises and a smart lock on the private entrance, so you can let yourselves in and out at any time.

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Portland, Maine, is a city with endless opportunities for adventure and exploration. On land or water, by foot or ferry, any way you choose to explore this vibrant seaside town will be richly rewarding.

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