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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

4.87 out of 5 average rating, 390 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!

Condo in Downtown Portland

4.96 out of 5 average rating, 169 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 suite in South Portland

5 out of 5 average rating, 183 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 suite in East End

4.91 out of 5 average rating, 207 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!

Rental unit in Downtown Portland

4.89 out of 5 average rating, 350 reviews

Central-Locale Studio in Vibrant Portland Maine!

Spacious studio with sitting area, queen size bed, table and chairs for dinning, kitchen and full bathroom. Newly updated appliances in a well maintained building. Wood floors lend charm, while modern decor makes for a contemporary feel. This comfortable space is perfect to come back to after exploring the surrounding neighborhood. The Studio is steps away from Portland's best restaurants, shops, nightlife and more!

Rental unit in West End

4.97 out of 5 average rating, 363 reviews

Large Sunny Apartment Near Downtown/Arts District

Quiet neighborhood, quick walk to downtown Portland. Short drive to beautiful sandy beaches. Newly furnished *3RD FLOOR* apartment. Spacious rooms with mansard roof ceilings. Washer and dryer. Off street parking for one car. Clean and well maintained. We happily welcome guests, but if you or someone in your group has difficulty with stairs this *3rd floor* apartment may not be the best fit for you or your group.

Rental unit in West End

4.94 out of 5 average rating, 465 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!

Rental unit in Downtown Portland

4.9 out of 5 average rating, 359 reviews

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

4.79 out of 5 average rating, 477 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.

Rental unit in Portland

4.96 out of 5 average rating, 160 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

Rental unit in Downtown Portland

4.96 out of 5 average rating, 559 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!

Rental unit in East End

4.85 out of 5 average rating, 516 reviews

Tip Top of the East End

The Height of Charm awaits you in an entirely outfitted private apartment atop AMAZING Munjoy Hill in Portland Maine. Enjoy a tranquill, panoramic water view from the kitchen, a comfortable new bed, and plenty of space for two in this clean, and cozy and sunny 1 bedroom apartment.

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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

Fort Allen Park11 locals recommend

Casco Bay Lines87 locals recommend

Victoria Mansion74 locals recommend

Bug Light29 locals recommend

Maine Narrow Gauge Railroad Company and Museum31 locals recommend

Other great vacation rentals in Old Port, Portland

Rental unit in West End

4.85 out of 5 average rating, 382 reviews

Quiet Retreat in the Heart of Portland's West End

Condo in Downtown Portland

4.98 out of 5 average rating, 116 reviews

Sparkling Clean, Old Port 2 bed, water view

Guest suite in South Portland

4.91 out of 5 average rating, 214 reviews

Top of the Hill So Po In Law

Rental unit in West End

4.94 out of 5 average rating, 168 reviews

Charming Modern West End Gem

Rental unit in Downtown Portland

4.93 out of 5 average rating, 612 reviews

Extraordinary Architectural Masterpiece Downtown

Rental unit in Downtown Portland

4.99 out of 5 average rating, 302 reviews

The Nauti Moose

Rental unit in Downtown Portland

4.8 out of 5 average rating, 508 reviews

Spacious Downtown 1 Bdrm King

Home in Portland

4.95 out of 5 average rating, 295 reviews

Explore Portland from a 18th-Century Victorian

Destinations to explore

Monthly Rentals Old Port