Vacation rentals in Old Port, Portland

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Top-rated vacation rentals in Old Port, Portland

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Top guest favourite

Apartment in East End

4.98 out of 5 average rating, 583 reviews

Amazing Views! Perfect Location. Loft style feel.

Oh the VIEW! City views and a beautiful park like old cemetery. Cozy, sunny private apartment in a quiet, Owner Occupied building. Perfect East End location for exploring all of Portland Just 2 blocks from Duckfat, Eventide and many restaurants, breweries and distilleries Comfy living room with a 55" TV and seating to take in the view. Fully equipped eat in kitchen, tile shower and a wonderful King size bed to watch the sun rise Includes Reserved Off street parking. License #STHR-000980

Top guest favourite

Apartment in East End

4.98 out of 5 average rating, 612 reviews

Cozy * Awesome Location * With Parking

Well -appointed one bedroom in Portland’s best neighborhood, the East End. A ten-minute walk to the Eastern Prom or the restaurants of the Old Port. This first-floor apartment has a modern vibe with artwork from local artists. I pay attention to details such as cleanliness, local coffee and Brooklinen linens and towels. Bathroom Newly Renovated 2023. TV is Roku Off-street parking included. One bedroom w/a queen and a queen sleeper-sofa. This is a non-smoking and non-vaping space. No pets.

Guest favourite

Apartment in Downtown Portland

4.96 out of 5 average rating, 283 reviews

Old Port 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.

Guest favourite

Condo in Downtown Portland

4.87 out of 5 average rating, 434 reviews

Renovated Exchange St. Loft w/Free Parking

This renovated loft-style condo is right in the heart of the Old Port. Located on Portland's bustling Exchange Street, the loft is central to everything the Peninsula has to offer. Elevator access will take you from the apartment to the secure lobby. From there, shops, restaurants, night life and the working waterfront are just steps outside the door. Free off street parking is available for one car a few blocks away or a convenient pay-to-park garage is located next to the building.

Top guest favourite

Apartment in West End

4.94 out of 5 average rating, 638 reviews

Historic Home in the West End. Private Parking.

With the Portland Museum of Art and the State Theater a 5 minute walk away, the Old Port just 15, this stunning apartment is just steps from the best eateries, arts & shopping the city has to offer. When you arrive, park your car in the private parking space and forget about it for a while! Built in 1835, this sunny and spacious second-floor apartment features 14-foot ceilings and original hardwood floors. A his and her bathroom is linked with a walk-through stone tiled shower.

Guest favourite

Apartment in East End

4.98 out of 5 average rating, 109 reviews

Harborview - Curated East End Escape w/ Parking

Harborview is a newly renovated, top-floor apartment perched on the edge of Munjoy Hill in Portland's East End. This home is a short stroll to the Eastern Promenade and the East End Beach, the Casco Bay Islands Ferry Terminal, and the historic Old Port. The apartment features a spacious open kitchen, dining, and living room floor plan adjoined by a large private deck. It's the perfect spot to gather, relax, and dine while enjoying the breathtaking views of Casco Bay!

Guest favourite

Apartment in Downtown Portland

4.89 out of 5 average rating, 428 reviews

Central-Local Studio in Vibrant Portland Maine!

Spacious and private studio apartment, 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!

Guest favourite

Apartment in West End

4.97 out of 5 average rating, 132 reviews

West End, Walk Anywhere-Stay a weekend or longer!

Wonderful West End location. Walker's paradise. 20 min stroll to the Arts District and Old Port. Steps from Tandem Bakery, Little Pig, Wayside Tavern, Local 188, Pai Men Miyake, Bramhall, Quiero Cafe, Chaval and many more. Private entrance, hardwood floors, original architectural features. New King size bed. Parking directly next to entry. Fully equipped kitchen. Loads of natural light. Quiet building for a wonderful Portland getaway.

Top guest favourite

Apartment in West End

4.98 out of 5 average rating, 342 reviews

Beautiful West End studio, hot tub, free parking

Charming, comfortable, well-appointed studio apartment, in an historic building, just steps away from everything downtown Portland has to offer: restaurants, museums, shopping, galleries, parks, Congress Street, and the Old Port. Close to Maine Medical and Mercy Hospital, the Portland Expo, Sea Dogs stadium, and Deering Oaks Park. The studio rental includes free parking for one car and exclusive use of a hot tub.

Guest favourite

Hotel room in Downtown Portland

4.93 out of 5 average rating, 200 reviews

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft hosted by The Docent’s Collection. Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

Top guest favourite

Guest suite in East End

4.99 out of 5 average rating, 185 reviews

Sunset Suite 42

Breathtaking views, privacy, and convenient location make Sunset Suite a great place to be while visiting ME! The great room with a cathedral ceiling and skylights offers the best of natural light... day and night! The Portland skyline is all yours from your private and expansive deck as you put your feet up and reminisce about your day and plan for the next.

Guest favourite

Apartment in Downtown Portland

4.95 out of 5 average rating, 690 reviews

Modern Studio Loft w/ Parking in Perfect Location

This spacious and comfortable studio loft is in the heart of Portland's Arts District. Located on the quieter end of Oak Street, the studio is within walking distance of everything Portland's peninsula has to offer. Complementary parking for one car is provided in a nearby lot. 2025 City of Portland registration STHR 000854