Apartment holiday rentals in Cumberland County

4.91 out of 5 average rating, 200 reviews

Clean and Bright, Two Blocks to the Prom!

Clean and renovated 1890 2nd floor 3-bedroom apartment two blocks from the Eastern Prom. Enjoy walks to great restaurants, coffee shops, bars, breweries and the East End Beach. Short taxi ride to everything else downtown Portland has to offer! Street parking only, but typically easy and free! Apartment living, some noise. Building is Owner Occupied w/ long term tenants. Please be respectful, no loud parties! A/C installed first week of June to last week of Sept. Listing # STHR-00840-2018

4.9 out of 5 average rating, 453 reviews

Beautiful Bright Oasis - Balcony & Parking

Welcome to The Port City Oasis, an Airbnb gem in Portland! This two-bedroom apartment offers vintage charm, cozy beds, and a private balcony. Just a 5-min walk to downtown and 15 mins to the Old Port, it's in a prime location for exploring Portland's shops, cafes, and restaurants. Please note that this 3rd-floor walk-up may not be suitable for guests with mobility issues. No matter what brings you to Portland, our comfortable and inviting space provides the perfect home base for your stay!

4.98 out of 5 average rating, 111 reviews

Cozy East End Apartment - Great location!

Location Location Location. 3 blocks from the ocean. This is our top floor apartment in a very quiet but very central part of Munjoy hill. Just 3 blocks up the street from the eastern promenade park and east end beach and only a block away to restaurants, cafes, and markets. As good as location gets for your stay in Portland. Our third floor apt is quiet and cozy and we hope you enjoy its character. Enjoy peaks of the water from the Queen BR. Pull out Queen sofa bed in the living room.

4.84 out of 5 average rating, 116 reviews

Sunny, Airy Portland East Bayside 2 Bedroom

Beautiful sunny 2 bedroom apartment in Portland's East Bayside neighborhood. In the past few years Portland has become known for its amazing restaurants as well as for it's charming cobble stone streets and waterfront. This private 2 bedroom apartment in an owner occupied house is close to restaurants, breweries, and only a short walk to the Old Port area. The first floor apartment has a large eat-in kitchen, a washer and drier, porch, heat and air conditioning, and a large living room.

4.91 out of 5 average rating, 249 reviews

Sunset Retreat with off-street parking

Newly remodeled, bright and airy 1-bedroom apartment two blocks from the best wineries/breweries and restaurants in Portland, and a 15 minute walk to the Old Port. This apartment has a view of back cove as well as a full open-concept kitchen. Stress-free stay with your own dedicated parking spot in a quiet neighborhood and high speed fiber WiFi (up to 1gb download & upload speed). Please note that this listing is only rented to guests with at least one review on their Airbnb account.

4.91 out of 5 average rating, 560 reviews

Sophisticated Charm at an unbeatable price!

Apartment is centrally located to all downtown amenities and transportation system. Located in the beautiful West End on a quiet residential street approximately 1 mile from the downtown area. Apartment (3rd floor) gets beautiful sun throughout and has all of the traditional charm and character of the West End homes but updated bathroom and kitchen, both recently remodeled in 2017. Rental includes access to one parking space for a small to mid size vehicle. STHR-001018-2019

4.79 out of 5 average rating, 611 reviews

Sunny Downtown 2 Bed Apt, Parking

The state of Maine requires all reservations must abide by current state travel restrictions. Please review before booking with us. Location location location! This apartment is centrally located in the trendy West End neighborhood of Portland, minutes away from great restaurants, coffee shops, museums and a 15-minute walk or a 5min taxi ride to the Old Port. An off-street parking spot is included. The apartment entry is entirely keyless and painless!

4.77 out of 5 average rating, 567 reviews

Stunning Congress St 1 bdr downtown

Perfect 1 bdrm apt located in the heart of Portland. Virtually everything the city has to offer within easy walking distance. Highlights include hardwood, brick, granite, and stainless steel. Brand new bed (spring 2023). If this one does not suit your needs please check out my other listings by double clicking on my profile picture. All apartments legally registered and inspected by the City of Portland. Thank you

4.94 out of 5 average rating, 524 reviews

Bright & Sunny West End Apartment.

This sunny 3rd-floor apartment is in a historic row house that was built in 1835. With the Portland Museum of Art and the State Theater a 5-minute walk away & the Old Port just 15, this home is steps from the best eateries, arts and shopping the city has to offer! When you arrive, park your car in your private spot behind the house and forget about it for a while.

4.79 out of 5 average rating, 555 reviews

Cityscape Loft. Central Location

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.

Top guest favourite

4.92 out of 5 average rating, 118 reviews

The Brew House - 2nd Floor Private Apartment

Portland ME Entire rental unit – 1 bedroom 900 square foot apartment located on Washington Ave, with off street parking. Just a few hundred feet from Portland’s artesian strip Known for its great restaurants breweries wineries and distilleries. Half mile to the eastern promenade and east end beach and less than a mile from the downtown area.

Top guest favourite