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Cabin and house vacation rentals in South Portland

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Top-rated vacation rentals in South Portland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Newly built private guest suite off Shore Road
Entire guesthouse · 3 guests · 2 beds · 1 bath
Newly built private guest suite off Shore RoadNewly built cozy above-garage guest suite with private entrance on dead end street. Bright & airy space, thoughtfully designed in charming, cozy neighborhood full of young families. Access to large network of trails in the 200 acre Land Trust and walking distance to beautiful cobblestone beach. Conveniently located to the shops and restaurants in town and minutes from the iconic Portland Head light located in Fort Williams park.
Oceanfront with amazing views and private entrance
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath
Oceanfront with amazing views and private entranceWe ask that all guests be fully vaccinated or tested for Covid just prior to arrival.
Beautiful West End studio, hot tub, free parking
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath
Beautiful West End studio, hot tub, free parkingCharming, comfortable, well-appointed studio apartment, in an historic building, just steps away from everything downtown Portland has to offer: restaurants, museums, shopping, galleries, parks, Congress Street, and the Old Port. Close to Maine Medical and Mercy Hospital, the Portland Expo, Sea Dogs stadium, and Deering Oaks Park. The studio rental includes free parking for one car and exclusive use of a private hot tub.

Vacation rentals for every style

Get the amount of space that is right for you

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  • Unique stays
  • SUPERHOST
    1. Entire rental unit
    2. Portland
    Modern East End studio, perfect Portland home base
    $75 per night
  • SUPERHOST
    1. Entire loft
    2. Portland
    Charming Arts District Studio with Parking
    $94 per night
  • SUPERHOST
    1. Entire rental unit
    2. Portland
    East End, Walk to the Old Port, with Parking
    $119 per night
  • SUPERHOST
    1. Entire rental unit
    2. Portland
    Extraordinary Architectural Masterpiece Downtown
    $132 per night
Portland Museum of Art
Art Museum · 163 locals recommend
Photo of Portland Museum of Art

The Museum's collection contains more than 17,000 fine and decorative works of art dating from the 18th century to the present. The collection includes paintings, sculpture, prints, photography, glass and ceramics, artists' books, furniture, and much more.

  • SUPERHOST
    1. Entire rental unit
    2. Portland
    Cheerful Arts District Studio with Free Parking
    $90 per night
  • SUPERHOST
    1. Hotel room
    2. Portland
    Inn at Park Spring 2 | Self Check In | Parking
    $73 per night
  • SUPERHOST
    1. Entire rental unit
    2. Portland
    Bright 1 bdrm in the Arts District w/free parking
    $116 per night
    1. Entire rental unit
    2. Portland
    Fabulous Studio w/ Free Parking & Great Location
    $103 per night
  • SUPERHOST
    1. Entire guest suite
    2. South Portland
    Apartment Near Willard Beach
    $144 per night
  • SUPERHOST
    1. Entire guest suite
    2. South Portland
    Top of the Hill So Po In Law
    $85 per night
  • SUPERHOST
    1. Entire residential home
    2. South Portland
    Cottage style home 2 blocks from the beach!
    $275 per night
    1. Entire rental unit
    2. South Portland
    Bay Windows at Willard Beach, New 3 BR, 1 BA
    $146 per night

Your guide to South Portland

All About South Portland

If Portland is Maine’s Manhattan, South Portland might be its Brooklyn — at least that’s the joke among some locals. As the state’s biggest city, Portland gets the lion’s share of the media attention, but its little sister across the Fore River is worth exploring all on its own. Creative entrepreneurs have decamped across the bay to open shops and restaurants, revitalizing walkable neighborhoods like Knightville and Meetinghouse Hill. South Portland is also home to a seemingly endless array of dog-friendly parks, beaches, and trails as well as craft breweries, postcard-perfect lighthouse landscapes, and interesting museums that celebrate Maine’s military and maritime history. To get there from Portland’s West End neighborhood, just cross the Casco Bay Bridge — in a car, on a bike, or on foot. From the other shore, you’ll get a nice view of Portland Harbor, and you can continue your car-free explorations on the Greenbelt Walkway or Spring Point Shoreway.


How do I get around South Portland?

Fly into Portland International Jetport (PWM), about a 15-minute drive from South Portland. You may choose to rent a car, though going without one here is possible. Three public bus routes connect South Portland’s Mill Creek Transit Hub to downtown Portland, the airport, the mall, and the beach (via the Willard Square stop).


When is the best time to stay in a vacation rental in South Portland?

Like everywhere else in Maine, South Portland is most popular in the summer, when Mainers can finally swap their long johns for T-shirts. Expect relatively clear skies and comfortable temperatures in the upper 60s to mid-70s Fahrenheit between June and Labor Day, and more than 15 hours of daylight during the longest days of summer. Come fall, you’ll need to pack jackets, coats, and scarves instead of shorts and swimsuits, but you’ll be rewarded with fewer crowds and trees ablaze in gorgeous tones of crimson and gold. By January, the mercury hovers around freezing, dipping to 16 degrees overnight, and there are only around nine hours of daylight. Rain falls throughout the year in South Portland, with snow more likely in January.


What are the top things to do in South Portland?

Fort Williams Park

This 90-acre park sits on the site of a decommissioned United States Army post that housed and trained troops during both world wars. Today, more than a million people come here each year to fly kites, ride bikes, and visit the iconic Portland Head Light and Museum, the oldest lighthouse in the state. The scenic shoreline is a popular backdrop for picnics and weddings.

Willard Beach

Locals love this relaxed, uncrowded sand-and-pebble beach, good for ocean swimming when the weather is nice. There’s a snack bar, showers, and tidepools that provide hours of entertainment for curious kids. Or just soak up the summer rays and watch the boats gently bobbing in the bay.

Spring Point Shoreway

Haven’t had your fill of lighthouses? There are two more awaiting you along this 1.6-mile pedestrian path and bikeway: the still-operational Spring Point Ledge Lighthouse, built in 1897, and the spark-plug-shaped Portland Breakwater Lighthouse, which dates back to 1875. Highlights along the way include a pair of sandy beaches and historic Fort Preble, built in 1808, where 23 captured Confederate raiders were imprisoned during the Civil War.