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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.

Hotel room in Arts District
Inn at Park Spring 4 | Self Check In | Parking
Location, Location, Location! Welcome to The Inn at Park Spring! Formerly the Park Spring Bed & Breakfast, we recently dropped the breakfast to serve Airbnb guests near and far as a boutique hotel. ROOM 4: By far our most spacious room, it is located on the third floor and has plenty of windows to bring in an abundance of afternoon sunshine. A queen bed, oversized headboard, sofa, and plants make up this bright retreat. The room also comes with one, off street parking spot just one block away.
G$13,508 GYD per night
SUPERHOST
Rental unit in Arts District
Open Concept Loft in the Heart of Downtown Center
In the heart of it all! This centrally located and roomy 1BR apartment is an ideal home base for exploring Portland. Perfect for a couple, but can accommodate up to 4 with a sofa bed. Located in a historic building built in 1890 in the center of downtown Portland, you'll enjoy a prime walkable location with plenty of space. You will see all around you the preservation of historic charm, while enjoying all the modern amenities in this beautifully preserved and tastefully remodeled apartment.
G$17,579 GYD per night
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Hotel room in West End
Skolfield Inn | Parking | Self-check-in | Garden 2
Welcome to The Skolfield Inn! ROOM 2: In this room you can relax on the couch with a book or snuggle up in bed to watch Netflix. While the room is bright and spacious, the bathroom is what keeps people coming back for more! With a double vanity, large marble glassed in shower, and original hardwood floors, you will look forward to your own little spa-like oasis. This room also comes with one, off street parking spot (cannot support larger SUVs/trucks).
G$11,458 GYD per night
SUPERHOST

Stay near Portland's top sights

Photo of Peaks Island
Peaks Island176 locals recommend
Photo of Portland Harbor Museum
Portland Harbor Museum349 locals recommend
Photo of The Maine Mall
The Maine Mall86 locals recommend
Photo of Fort Williams Park
Fort Williams Park229 locals recommend
Photo of State Theatre
State Theatre114 locals recommend
Photo of DiMillo's On The Water
DiMillo's On The Water101 locals recommend

Portland summer vacation rentals

Rental unit in Portland
Self-check-in | Desk | Washer + Dryer | Kitchen 2
G$11,368 GYD per night
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Hotel room in West End
Morrill Mansion | 2 | Self Check In | Parking
G$10,010 GYD per night
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Rental unit in West End
Spacious, walk to Downtown, WFH
G$15,316 GYD per night
Rental unit in Downtown Portland
West End One Bed/Bath Urban Retreat w/ Parking
G$17,246 GYD per night
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Rental unit in Portland
Parkside Retreat on Portland's Eastern Promenade
G$18,845 GYD per night
Rental unit in Portland
Bright & Spacious Apartment with Amazing Shower
G$21,021 GYD per night
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Rental unit in Portland
RETRO BnB in the Heart of East End Portland
G$18,482 GYD per night
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Rental unit in West End
Airy+Modern 1BR In Portland's Historic West End!
G$19,056 GYD per night
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Rental unit in Portland
Private 1 Bedroom Apt Close to the Old Port
G$15,226 GYD per night
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Rental unit in Downtown Portland
Updated stylish 1 BR Downtown Apt
G$21,106 GYD per night
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Rental unit in Portland
Modern East End studio, perfect Portland home base
G$15,920 GYD per night
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Rental unit in Portland
Charming Downtown 1BR w/ Parking, Walk to Old Port
G$32,775 GYD per night
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Portland winter vacation rentals

Hotel room in West End
Morrill Mansion Inn | 7 | Self Check In | Parking
G$11,758 GYD per night
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Rental unit in Arts District
Fabulous Studio w/ Free Parking & Great Location
G$18,603 GYD per night
Condo in Arts District
Stylish Downtown Condo
G$16,617 GYD per night
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Rental unit in Arts District
Charming Portland 1 bdrm, close to everything
G$23,638 GYD per night
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Rental unit in West End
Self-check-in | Parking | Washer + dryer | Desk |3
G$13,478 GYD per night
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Hotel room in Arts District
Inn at Parkspring 5 | Self Check In | Parking
G$11,638 GYD per night
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Hotel room in West End
Skolfield Inn | Parking | Self-check-in | Garden 1
G$10,884 GYD per night
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Rental unit in West End
Quiet Retreat in the Heart of Portland's West End
G$18,482 GYD per night
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Rental unit in Portland
Beautiful 1st Floor Apartment & Amazing Shower
G$17,066 GYD per night
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Guest suite in Portland
Private Suite in the Heart of East End Portland
G$16,279 GYD per night
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Hotel room in Downtown Portland
Artful One Bedroom Urban Home in the Old Port
G$31,538 GYD per night
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Rental unit in Arts District
Cozy Studio Walkable to Downtown Portland
G$15,105 GYD per night

Portland beach vacation rentals

Private room in Portland
Dog-Friendly Upstairs Room with Separate Entrance
G$11,095 GYD per night
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Rental unit in Downtown Portland
Beautiful West End studio, hot tub, free parking
G$35,126 GYD per night
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Rental unit in Downtown Portland
2br, Office, & Parking in West End: Gull's Landing
G$18,056 GYD per night
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Rental unit in West End
Cozy West End apartment minutes from the Old Port.
G$22,281 GYD per night
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Rental unit in West End
King Size Bed ♦ West End Studio ♦ Walk to Old Port
G$12,725 GYD per night
Rental unit in Downtown Portland
Beautiful Apt in Historic Building - Old Port
G$28,191 GYD per night
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Rental unit in Portland
Hip & Cozy, high end Modern Design
G$19,901 GYD per night
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Rental unit in Portland
The Aerie
G$21,106 GYD per night
Rental unit in Downtown Portland
Renovated 1 BR Downtown Apt w/backyard
G$21,106 GYD per night
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Rental unit in Portland
Portland, Munjoy Hill ~clean & stylish haven
G$26,232 GYD per night
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Rental unit in Portland
Adorable getaway on the Eastern Promenade
G$20,895 GYD per night
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Guest suite in South Portland
Apartment Near Willard Beach
G$11,728 GYD per night
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Your guide to Portland

Introduction

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.


When is 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, making it a popular time to stay in one of the area’s vacation rentals. 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.


What are the 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.

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