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.

Guest favorite
Guest suite in Portland
Sunny West End Guest Suite with Harbor Views
Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. This garden oasis with stone walls and salt water pool (open seasonally) is walking distance to downtown. (Portland City Permit: 20185360-ST) Your safety is important to us! We are following strict guidelines for sanitizing all linens, towels, furniture, objects and surfaces. Airbnb has an incredibly thorough and helpful protocol! All doorknobs, light switches and hand-touched surfaces will also be alcohol sanitized for your arrival! Here is a link to the protocol we are following: https://www.airbnb.com/resources/hosting-homes/a/airbnbs-5-step-cleaning-process-explained-187. Please let us know if you have any questions! This guest suite is a private, two-floor space attached to our house. It has its own front and back entrances and is separated by locked doors upstairs and downstairs from the main part of the house. The suite is light and sunny and a wonderful place to rest. The downstairs sitting room has a table for two and built in seating for relaxing and enjoying the water views or watching tv. The bedroom and bathroom are upstairs with lovely views. You will given your unique code for the guest suite door which enables you to come and go on your own timing. Parking is always available in front of the house or within a block. Please note that parking is prohibited on our side of the street on Monday nights through Tuesday mornings the 2nd and 4th Monday of the month. You can park on the opposite side of the street. The guest suite is attached to our house, but with its own front and back entrances. The day before you arrive we will send you instructions about your arrival. There is a key code so you can enter on your own. We may see each other on the back deck or in the yard at the pool. We have two dogs and you might see them in the yard and also coming up the stairs to our back deck door. We are right next door if you need anything or have any questions, and are also very conscious of your privacy. Please feel free to reach out if you need anything. We love Portland! Just let us know if you would like advice on local hikes, beaches, entertainment or great food. Portland has incredible restaurants! Most within walking distance from the house. The house is in the historic West End neighborhood overlooking the working harbor of the Fore River. Within walking distance are Portland's Old Port and Arts Districts, as well as the Saturday Farmers' Market in Deering Oaks Park. Parking is very easy on the street in front of the house. You can drive to local spots like the beautiful lighthouse at Fort Williams in Cape Elizabeth or the beaches in Scarborough, but you can walk to downtown Portland in 15-20 minutes. It's great to visit Portland on foot. You can walk Danforth Street all the way down to the Old Port shopping area. Here are directions for a nice walk to the Old Port: Turn right on Danforth when leaving the house. Take your first left on Emery Street. At the four way stop, turn right on Spring Street. Take Spring Street for just over a mile. After passing Temple Street, take your first right onto Exchange Street. This is the heart of the Old Port. Have fun!! Please Note: All Guests agree to indemnify and hold the Property Owners harmless from any liability for personal injury or property damage sustained by Guest or parties invited onto the property by Guest.
Mar 24 – 29
$142 per night
4.99 out of 5 average rating, 264 reviews
Superhost
Apartment in Portland
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!
Oct 31 – Nov 7
$68 per night
4.82 out of 5 average rating, 347 reviews
Guest favorite
Apartment in Portland
Munjoy Hill, East End 1 BR Portland, ME
The Portland Observatory marks your way home to this apartment atop Munjoy Hill. Furnished for guests, private entrance, 1st floor unit of our 2 unit home of twenty years. BEST LOCATION! Skip the car. WALK to restaurants, music, shops, breweries, beach, parks, & historic Old Port. Stones throw to fresh produce, bakeries, wine & spirits. Furnished with LOCAL ART (made by your host in adjacent studio) the cozy apartment offers humble elegance. Just arrive, fun awaits. All are welcome here.
Mar 31 – Apr 7
$92 per night
4.97 out of 5 average rating, 351 reviews

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
Guest favorite
Apartment in South Portland
Sunny and beautiful brick house apartment
Oct 18 – 25
$150 per night
4.91 out of 5 average rating, 148 reviews
Guest favorite
Guest suite in South Portland
Oceanfront with amazing views and private entrance
Aug 25 – 30
$300 per night
5.0 out of 5 average rating, 674 reviews
Guest favorite
Apartment in Scarborough
Your beach retreat - eat, sleep, beach, repeat!
Apr 25 – May 2
$92 per night
4.83 out of 5 average rating, 609 reviews
Guest favorite
Apartment in Portland
Cozy West End apartment minutes from the Old Port
Jun 10 – 17
$190 per night
4.94 out of 5 average rating, 609 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
Guest favorite
Apartment in Portland
Extraordinary Architectural Masterpiece Downtown
Dec 13 – 20
$275 per night
4.93 out of 5 average rating, 592 reviews
Guest favorite
Apartment in Portland
Open Concept Loft in the Heart of Downtown Center
Apr 25 – May 2
$108 per night
4.9 out of 5 average rating, 176 reviews
Guest favorite
Guest suite in Cumberland
Springer Park! adorable guesthouse very stylish!
May 14 – 21
$122 per night
4.92 out of 5 average rating, 108 reviews
Guest favorite
Apartment in Portland
Large Sunny Apartment Near Downtown/Arts District
Oct 31 – Nov 7
$145 per night
4.97 out of 5 average rating, 347 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
Superhost
Home in Falmouth
Amazing Bay View Home with Hot Tub
Nov 20 – 27
$151 per night
4.85 out of 5 average rating, 172 reviews
Guest favorite
Home in Gorham
Beautiful Home In Gorham Maine
Dec 5 – 12
$152 per night
4.99 out of 5 average rating, 138 reviews
Guest favorite
Home in Brunswick
A cozy, cute and comfortable house.
May 14 – 21
$130 per night
4.93 out of 5 average rating, 212 reviews
Guest favorite
Home in Freeport
"The Cozy Cottage in the heart of Freeport Village
Feb 19 – 26
$139 per night
4.99 out of 5 average rating, 162 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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