Skip to content

Portland vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Portland

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

Superhost
Apartment in Portland
RETRO BnB in the Heart of East End Portland
Retro BnB in The Heart of Portland's East End offers a combination of 70's mod charm with a vibrant comfortable style. Sunny, first floor back apartment with private entrance, one hybrid coil/thermarest queen bed overlooking yard with lovely perennial garden, bathroom with central, well appointed kitchen/dining room. This space is perfect for one couples looking for a cozy home base hideaway. A short walk to gourmet restaurants, cafes, East End beach and all Portland peninsula has to offer!
$87 per night
Superhost
Apartment in Portland
Huge Dreamy urban Artist-designed loft
Truly unique, Local Artist Designed 1 bedroom loft, very spacious, natural light filled 2 story apartment in an 1875 built Victorian home in the desirable west end historic neighborhood. Located a block from the Victorian mansion, a very central location, 10 minutes scenic stroll to renowned restaurants, situated just far enough from town for a more tranquil experience. birds sing. A very special spot full of character and charm. Views of the harbor from private deck. Driveway parking
$111 per night
Superhost
Apartment in Portland
Cityscape Loft. Prime Location. Walk Everywhere!
Beautiful, spacious, 1 bedroom heart of the city urban apartment featuring 12 foot ceilings, high end kitchen and bath, refinished hardwood floors in a location that is absolutely terrific. Amazing City Scape Views! This is a second floor apartment. Expect stairs. Sleeps 3 : 1 Bedroom with queen bed and there is a Futon in small auxiliary room.
$92 per night

Stay near Portland's top sights

Portland Harbor Museum347 locals recommend
The Maine Mall86 locals recommend
Peaks Island176 locals recommend
DiMillo's On The Water101 locals recommend
Portland International Jetport50 locals recommend
Fort Williams Park229 locals recommend

Portland beach vacation rentals

Superhost
Apartment in Portland
*Serene* West End 2BR w/ Balcony: The Mermaid Cove
$109 per night
Superhost
Apartment in Portland
Walk-able Portland Studio
$105 per night
Superhost
Apartment in Portland
Beautiful Apt in Historic Building - Old Port
$169 per night
Superhost
Apartment in Portland
Amazing Views! Perfect Location. Loft style feel.
$138 per night
Superhost
Guest suite in South Portland
Bright Guest Studio Near Lighthouses and Beach
$101 per night
Superhost
Apartment in Portland
Hip & Cozy, high end Modern Design
$130 per night
Superhost
Apartment in Portland
The Howard on Munjoy Hill
$109 per night
Superhost
Apartment in Portland
Petit Pad Atop Munjoy Hill+Steps to Eastern Prom!
$111 per night
Superhost
Apartment in Portland
Historic Home in the West End. Private Parking.
$143 per night
Superhost
Apartment in Portland
The East Den! Easy parking, next to breweries!
$117 per night
Superhost
Apartment in Portland
Light-Filled Spacious Apartment in Ideal Location
$171 per night
Superhost
Apartment in Portland
Downtown Portland 1 Bedroom
$128 per night

Private Portland vacation rentals

Superhost
Loft in Portland
Central Arts District Studio with Free Parking
$102 per night
Superhost
Condo in Portland
Stylish Downtown Condo
$114 per night
Superhost
Apartment in Portland
Charming Downtown 1BR w/ Parking, Walk to Old Port
$110 per night
Superhost
Cottage in Portland
Cozy & Quiet Modern Cottage
$80 per night
Superhost
Apartment in Portland
Open Concept Loft in the Heart of Downtown Center
$113 per night
Superhost
Guest suite in Portland
Studio, Walk to everything, Parking
$96 per night
Superhost
Apartment in Portland
* East End, Cozy Vibe and Luxury Linens w Parking
$145 per night
Superhost
Apartment in Portland
Charming Modern West End Gem
$128 per night
Superhost
Apartment in Portland
Updated stylish 1 BR Downtown Apt
$100 per night
Superhost
Apartment in Portland
Quaint West End Flat, 1 bedroom, lots of character
$120 per night
Superhost
Apartment in Portland
Spacious Downtown 1 Bdrm King
$142 per night
Superhost
Apartment in Portland
Tip Top of the East End
$120 per night

Portland house rentals

Superhost
Home in Portland
Explore Portland from a 18th-Century Victorian
$179 per night
Superhost
Home in Portland
Perfectly Portland
$179 per night
Superhost
Home in Portland
Quiet Comfy Victorian Escape
$204 per night
Superhost
Home in Lisbon
Unplug at a Beachy Bolthole with Classic New England Style
$65 per night
Superhost
Home in Scarborough
Swim spa under the starry night pool/hot tub/sauna
$337 per night
Superhost
Home in Falmouth
Amazing Bay View Home with Hot Tub
$230 per night
Superhost
Home in Falmouth
Oceanside Escape ◆ Perfect family Getaway!
$125 per night
Superhost
Home in Lebanon
Beautiful, Peaceful, Maine Getaway House
$105 per night
Superhost
Home in Freeport
The Outlet House, Comfortable Cottage
$142 per night
Superhost
Home in Westbrook
Reno Barn w/ Charm! Near Breweries & Airport
$126 per night
Superhost
Home in Saco
Oceanfront w/ Stunning views and Private Deck☀️🏖
$240 per night
Superhost
Home in Kennebunkport
“The Nest" Quiet & Stylish Oasis
$105 per night

Quick stats about vacation rentals in Portland

Total rentals

1.4K properties

Rentals with dedicated workspaces

720 properties have a dedicated workspace

Rentals with a pool

40 properties have a pool

Pet-friendly rentals

350 properties allow pets

Family-friendly rentals

760 properties are a good fit for families

Total number of reviews

144K 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.

Destinations to explore

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