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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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Apartment in Portland

4.88 out of 5 average rating, 384 reviews

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!

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 115 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

Guest favourite

Condo in Portland

4.96 out of 5 average rating, 166 reviews

"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.

Guest favourite

Apartment in Portland

4.9 out of 5 average rating, 291 reviews

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 favourite

Guest suite in South Portland

5.0 out of 5 average rating, 176 reviews

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 favourite

Guest suite in Portland

4.91 out of 5 average rating, 201 reviews

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!

Guest favourite

Apartment in Portland

4.94 out of 5 average rating, 458 reviews

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!

Apartment in Portland

4.79 out of 5 average rating, 470 reviews

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.

Guest favourite

Apartment in Portland

4.96 out of 5 average rating, 155 reviews

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

Guest favourite

Loft in South Portland

5.0 out of 5 average rating, 110 reviews

Serene studio apartment, close to everything.

Welcome to South Portland! Your spacious studio apartment with private entrance is a short walk to Fore River Brewing, Lincoln & Main/Electric Bike Cafe & Winery and the Greenbelt Walkway. A 10-min Uber ride will take you to the Old Port and South Portland staples like Willard Beach and Scratch bakery.

Guest favourite

Apartment in Portland

4.96 out of 5 average rating, 549 reviews

Charming West End Hideaway. Private Parking

Built in 1835, this historical home on the West End is just 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. This cozy second-floor apartment is the perfect place for a getaway!

Guest favourite

Apartment in Portland

4.94 out of 5 average rating, 606 reviews

Extraordinary Architectural Masterpiece Downtown

Dan's place is close to nightlife, public transport, the city center, and parks. You’ll love his place because of the ambiance, the outdoors space, the light, the neighborhood, and the comfy bed. The suite is perfect for couples, solo adventurers, and business travelers.

Vacation rentals for every style

Get the amount of space that is right for you.

Hotels

Stylish accommodations and amenities

Unique stays

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Homes

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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

Merrill Auditorium30 locals recommend

DiMillo's On The Water101 locals recommend

Eventide Oyster Co.272 locals recommend

Portland Lobster Co131 locals recommend

The Highroller Lobster Co61 locals recommend

Js Oyster83 locals recommend

Other great vacation rentals in Old Port, Portland

Guest favourite

Apartment in East End

4.98 out of 5 average rating, 500 reviews

East End * Bella Casetta w Parking

Guest favourite

Condo in Portland

4.98 out of 5 average rating, 114 reviews

Sparkling Clean, Old Port 2 bed, water view

Apartment in Downtown Portland

4.82 out of 5 average rating, 426 reviews

Walk-able Portland Studio

Guest favourite

Apartment in Portland

4.88 out of 5 average rating, 381 reviews

Updated stylish 1 BR Downtown Apt

Guest favourite

Apartment in Downtown Portland

4.99 out of 5 average rating, 291 reviews

The Nauti Moose

Guest favourite

Apartment in West End

4.99 out of 5 average rating, 302 reviews

Quiet West End Retreat - parking - 100% Non Smoker

Guest favourite

Apartment in Portland

4.94 out of 5 average rating, 119 reviews

Right in the City 2 Bedroom w/ Laundry in Unit

Guest favourite

Guesthouse in Portland

4.95 out of 5 average rating, 282 reviews

Beautiful large studio on the ocean.

Destinations to explore

Monthly Rentals Old Port