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Vacation rentals in Old Port, Portland

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Top-rated vacation rentals in Old Port, Portland

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Rental unit in East End

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!

Rental unit in West End

Quiet West End Retreat - parking - 100% Non Smoker

Quiet, sunny studio apartment in owner-occupied 4 unit building conveniently located in the historic West End residential neighborhood. It’s a short walk to all that Portland has to offer. Off-street parking for 1 car. Relax on the patio and soak in the summer warmth. Perfect for a single or couple traveling to the area. No complicated checkout procedures! Just leave the key in the lock on your way out and we will take care of the rest. 100% Non- smoking guests only, No Exceptions.

Condo in Downtown Portland

"Cornelia" Penthouse Waterfront Suite

2023 City of Portland Registration #20185280-ST Penthouse suite w/modern amenities, exposed beams and brick, poplar walls. Rooftop deck w/views of harbor and city. Separate master suites with custom showers and heated bathroom floors; one with soaking tub. Gas-fired Jotul stove in living room. Washer/dryer in unit. Easy elevator access. Spacious kitchen with granite countertops and wine cooler. Please note: animals (including assistance animals) not allowed due to owner's health.

Rental unit in Downtown Portland

Walk-able Portland Studio

NEWLY RENOVATED! Cozy studio apartment in a historic building, located in Portland's East End Neighborhood. This location can't be beat! The Space features original hardwood floors, and large windows, subway tiled shower and thoughtful decor. Portland Food Co-Op is directly next door, as is the Walgreen's. Walking distance to Eventide, Honey Paw, Duck Fat, Hugos, Little Woodfords, LB Kitchen, Washington Ave Breweries and Distilleries and Old Port shopping district.

Rental unit in East End

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

Rental unit in Portland

Charming Downtown 1BR w/ Parking, Walk to Old Port

Enjoy your relaxing weekend in Portland with this wonderfully located 1 bedroom apartment located downtown! During your stay you can walk five minutes to Portland favorites such as Tandem Coffee Shop, Hot Suppa, and Bramhall. Other fun activities include watching a SeaDog’s game or visiting the farmer’s market on Saturdays at Deering Park, which are also a less than 10 minute walk! This airbnb features air conditioning, washer/dryer, and full kitchen.

Guest suite in South Portland

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer and cozy couch for lounging.

Guest suite in East End

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

Rental unit in West End

No cleaning fee! Location, location! And parking!

At Location Location! You can be assured that we take care of all the cleaning… so please be on vacation! This lovely, simple 1 bedroom apartment is in the heart of the Portland's West End. Just around the corner, a foodie paradise! Zu bakery, Chaval, Pan Men Miyake, Tandem bakery, El Corazon and Local 188 many others. Just down the street, Maine Med,Mercy Hospital, PMA, art galleries, shopping & the Old Port!

Rental unit in Downtown Portland

Renovated 1 BR Downtown Apt w/backyard

Large first floor 1 BD apt with a small backyard/patio in a brick Victorian era home in Portland’s West End. The Old Port is only a 7min walk. The building is by Harbor View Memorial Park and Casco Bay bridge that connects Portland with South Portland, Cape Elizabeth, Scarborough, beaches and parks. Not to forget, Portland was named “City of the Year” in 2018 in Bon Appetit.

Rental unit in Downtown 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.

Rental unit in Portland

Compact & Complete in residential neighborhood

Completely renovated ground level apartment in Deering section of Portland. Walk to off-peninsula restaurants, coffee and wine shops. Nearby trails for walking or biking. Near UNE's Portland Campus. On bus line to easily reach downtown Old Port area, USM and other attractions. Off street parking for your car. Portland STHR-0010302019

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Popular amenities for Old Port, Portland vacation rentals

Free parking on premises

Air conditioning

Stay near Old Port, Portland's top sights

Portland Museum of Art412 locals recommend

Casco Bay Lines87 locals recommend

Fort Allen Park11 locals recommend

Monument Square12 locals recommend

Merrill Auditorium30 locals recommend

Portland Observatory132 locals recommend

Other great vacation rentals in Old Port, Portland

Rental unit in West End

Large Sunny Apartment Near Downtown/Arts District

Guest suite in South Portland

Top of the Hill So Po In Law

Guest suite in Portland

Sunflower Retreat in North Back Cove

Rental unit in West End

Airy+Modern Studio + Portland's Historic West End!

Rental unit in Downtown Portland

Extraordinary Architectural Masterpiece Downtown

Tiny home in Portland

The Garden Cabin Tiny Home

Rental unit in West End

Parking | Self-check-in | Washer+Dryer | Kitchen 5

Home in Portland

Explore Portland from a 18th-Century Victorian

Destinations to explore

Monthly Rentals Old Port