Vacation rentals in Old Port, Portland

4.98 out of 5 average rating, 693 reviews

Guest suite in East End

PRlVATE SUlTE in the Heart of East End Portland

Private Suite in the Heart of East End Portland. Sunny, elegant, Victorian studio with private entrance, bathroom and mini-kitchen area. This location is walkable to award winning restaurants, excellent cafes, the East End Beach where you can rent kayaks, ferries to the islands and more! A perfect romantic getaway close to anything you want to come to Portland to see and do, yet in the quiet, tree lined neighborhood of Munjoy Hill and the scenic East End. See guidebook included in this listing:)

4.98 out of 5 average rating, 611 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.

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

Condo in Downtown Portland

4.87 out of 5 average rating, 433 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.

4.94 out of 5 average rating, 638 reviews

Apartment in West End

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.

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!

Loft in Downtown Portland

4.94 out of 5 average rating, 689 reviews

Central Arts District Studio with Free Parking

2025 City of Portland registration STHR 000854 Enjoy the quieter end of Oak Street in the heart of Portland's Arts District. Abundant dining, shopping, galleries and museums are steps from this home-away-from-home studio apartment. This is a perfect space for couples, solo adventurers and business travelers. Easily walk to everything the peninsula has to offer from this centrally located studio apartment! Complementary off-street parking for one car available.

4.92 out of 5 average rating, 305 reviews

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!

4.98 out of 5 average rating, 342 reviews

Apartment in West End

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.

4.77 out of 5 average rating, 265 reviews

The Aerie

My place is 1.5 blocks from the Eastern Prom and close to the Old Port, downtown, art and culture, parks, and restaurants and dining. My place is good for couples, solo adventurers, business travelers. Real full bed + ikea sofa can be a single bed as well. Expansive Casco Bay views. The studio apartment is on the third floor of a 3-unit building. Unfortunately at this time I cannot allow dogs.

4.99 out of 5 average rating, 185 reviews

Guest suite in East End

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.