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Vacation rentals in Portland

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Top-rated vacation rentals in Portland

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

Guest favourite
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: 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.
May 13 – 20
$231 CAD per night
Guest favourite
Apartment in Portland
Modern East End studio, perfect Portland home base
Enjoy all that Portland has to offer from this clean, modern, and spacious studio in the city's hippest neighborhood. Walk one block to enjoy Duckfat frites at the Oxbow beer garden or head down Washington Ave to sample the best restaurants in Portland including Drifter's Wife, Cong Tu Bot, and Izakaya Minato, among others. Walk 5 mins up Munjoy Hill to picnic on the Eastern Promenade overlooking Casco Bay or 10 mins down into the Old Port. Do it all from this beautiful and private apartment!
Mar. 18 – 25
$169 CAD per night
Guest favourite
Apartment in Portland
"Percival" Penthouse Suite - Amazing Harbor Views
2023 City of Portland Registration #20182242-ST Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.
Nov. 7 – 14
$773 CAD 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

Other great vacation rentals in Portland

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Guest suite in South Portland
Top of the Hill So Po In Law
Mar. 13 – 20
$114 CAD per night
Guest favourite
Apartment in Portland
Amazing Views! Perfect Location. Loft style feel.
Apr. 9 – 16
$222 CAD per night
Guest favourite
Guest suite in Portland
Garden Suite @ A Peaceful Oasis on Munjoy Hill
Dec. 18 – 25
$167 CAD per night
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Crooked Reflections, Riverside Retreat - Hot Tub
Aug. 13 – 20
$1,057 CAD per night
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Cozy Rock Cabin #thewaylifeshouldbe
Guest favourite
Apartment in Portland
Historic Munjoy Hill Retreat-Rooftop Water Views.
Nov. 10 – 17
$446 CAD per night
Guest favourite
Guest suite in Portland
West End Artist's Getaway
Apr. 25 – May 2
$199 CAD per night
Apartment in Portland
Spacious and Comfortable Private Apartment
Nov. 12 – 19
$129 CAD per night
Guest favourite
Apartment in Portland
Comfy Munjoy Hill Getaway with Private Entrance
Mar. 9 – 16
$168 CAD per night
Guest favourite
Apartment in Portland
Historic + Modern, Sun Filled West End 1BR Apt.
Nov. 13 – 20
$238 CAD per night
Guest favourite
Barn in Portland
Garrison Cove Studio
Nov. 3 – 10
$256 CAD per night
Guest favourite
Guesthouse in Cape Elizabeth
Newly built private guest suite off Shore Road
May 7 – 14
$233 CAD 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

Destinations to explore

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