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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.

Superhost
Apartment in Portland
Bright & Spacious Apartment with Amazing Shower
Spend your vacation, work-trip, or weekend getaway in our lovely, downtown apartment. Apartment 3 is located on the third floor where you have access to all our modern appliances: refrigerator, microwave, dishwasher, washer and dryer combo unit. We have a luxurious shower, a queen bed in the bedroom, and a pull-out couch with a queen mattress in the living room. Both the bedroom and living room have large, flat-screen TVs and in the living room you will find a luxurious leather loveseat.
G$17,023 GYD per night
Guest favorite
Apartment in Portland
Modern Cozy Vibe in East End w Parking
Well -appointed one bedroom in Portland’s best neighborhood, the East End. A ten-minute walk to the Eastern Prom or the restaurants of the Old Port. This first-floor apartment has a modern vibe with artwork from local artists. I pay attention to details such as cleanliness, local coffee and Brooklinen linens and towels. Bathroom Newly Renovated 2023. TV is Roku Off-street parking included. One bedroom w/a queen and a queen sleeper-sofa. This is a non-smoking and non-vaping space.
G$22,355 GYD 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.
G$19,784 GYD per night

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
Allagash Brewing Company156 locals recommend
Thompson Point28 locals recommend

Portland beach vacation rentals

Guest favorite
Apartment in Portland
Light-Filled Spacious Apartment in Ideal Location
G$35,744 GYD per night
Guest favorite
Apartment in Portland
Huge Dreamy urban Artist-designed loft
G$21,100 GYD per night
Guest favorite
Apartment in Portland
Adorable getaway on the Eastern Promenade
G$15,661 GYD per night
Guest favorite
Apartment in Portland
Beautiful West End studio, hot tub, free parking
G$32,068 GYD per night
Guest favorite
Apartment in Portland
*Serene* West End 2BR w/ Balcony: The Mermaid Cove
G$23,282 GYD per night
Guest favorite
Apartment in Portland
Modern East End studio, perfect Portland home base
G$15,780 GYD per night
Guest favorite
Apartment in Portland
Hip & Cozy, high end Modern Design
G$24,656 GYD per night
Guest favorite
Apartment in Portland
The East Den! Easy parking, next to breweries!
G$24,386 GYD per night
Guest favorite
Apartment in Portland
The Howard on Munjoy Hill
G$22,742 GYD per night
Guest favorite
Apartment in Portland
Beautiful Apt in Historic Building - Old Port
G$28,570 GYD per night
Guest favorite
Apartment in Portland
Portland, Munjoy Hill ~Clean & Stylish Haven
G$30,334 GYD per night
Guest favorite
Apartment in Portland
Lobster Trap - Munjoy Hill East End Cozy
G$21,487 GYD per night

Private Portland vacation rentals

Guest favorite
Guest suite in Portland
Sunny West End Guest Suite with Harbor Views
G$28,242 GYD per night
Superhost
Apartment in Portland
All for you! Perfect Location!
G$16,736 GYD per night
Guest favorite
Guest suite in Portland
Garden Suite @ A Peaceful Oasis on Munjoy Hill
G$16,590 GYD per night
Guest favorite
Apartment in West End
Historic + Modern, Sun Filled West End 1BR Apt.
G$21,338 GYD per night
Guest favorite
Apartment in Portland
Beautiful Bright Oasis - *Balcony & Parking*
G$18,977 GYD per night
Superhost
Apartment in Portland
Bright & Sunny Apartment with Patio
G$14,345 GYD per night
Guest favorite
Guest suite in Portland
Studio, Walk to everything, Parking
G$19,874 GYD per night
Guest favorite
Guest suite in Portland
Sunflower Retreat in North Back Cove
G$15,541 GYD per night
Superhost
Apartment in Portland
Sophisticated Charm at an unbeatable price!
G$29,886 GYD per night
Guest favorite
Apartment in Portland
Open Concept Loft in the Heart of Downtown Center
G$21,608 GYD per night
Guest favorite
Apartment in Portland
Quiet West End Retreat - parking - 100% Non Smoker
G$33,472 GYD per night
Guest favorite
Apartment in Portland
Apt with Hot Tub & Parking in Victorian Mansion
G$24,328 GYD per night

Portland house rentals

Guest favorite
Home in Portland
Perfectly Portland
G$26,089 GYD per night
Guest favorite
Home in Lisbon
Unplug at a Beachy Bolthole with Classic New England Style
G$13,598 GYD per night
Guest favorite
Home in Lebanon
Beautiful, Peaceful, Maine Getaway House
G$21,966 GYD per night
Guest favorite
Home in Scarborough
Swim spa under the starry night pool/hot tub/sauna
G$83,255 GYD per night
Guest favorite
Home in Saco
Oceanfront w/ Stunning views and Private Deck☀️🏖
G$47,325 GYD per night
Guest favorite
Home in Portland
Explore Portland from a 18th-Century Victorian
G$37,447 GYD per night
Guest favorite
Home in Portland
3 bedroom house in the heart of Portland
G$89,657 GYD per night
Guest favorite
Home in Acton
The ZEN welcomes you, your home away from home.
G$41,631 GYD per night
Guest favorite
Home in Freeport
The Outlet House, Comfortable Cottage
G$28,541 GYD per night
Guest favorite
Home in Portland
Quiet Comfy Victorian Escape
G$47,219 GYD per night
Guest favorite
Home in Arundel
NewBuilt/HotTub/Great Location-4 min Kennebunkport
G$64,254 GYD per night
Guest favorite
Home in Bath
Gorgeous Winter Studio Getaway on the Kennebec
G$23,102 GYD per night

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.

Destinations to explore

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