Vacation rentals in Old Port District

Stylish 3BR/2BA Close to Downtown with Parking

Gorgeous 3 bedroom, 2 full bath apartment ideally located in Portland’s Oakdale neighborhood with parking! Close to downtown, grocery stores, and the farmers market at Deering Oaks Park! The space features an oversized entryway, office, cozy living room, dining room, kitchen with large pantry and a huge back deck perfect for outdoor enjoyment. Charm and character abound with French doors, built-ins, beautiful molding, hardwood floors and soaring ceilings. Comfortable queen beds in each bedroom!

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

Luxurious Two Bedroom Loft Adorned with Local Art

Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). 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.

4br2ba House+parking@PeacefulOasis on Munjoy Hill

This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants, breweries and the Old Port. -Main floor: well-equipped kitchen + open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 twin) + bath -Garden level: 1BR/1 bath (queen) with private entrance - Off-street parking for 1 car This charming home @ A Peaceful Oasis offers plenty of space, privacy & comfort, making it the perfect home base for your stay.

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.

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!

Bright and cozy Munjoy Hill neighborhood apartment

Bright and cozy apartment in Portland's Munjoy Hill neighborhood with private backyard deck. Short walk (like a minute!) to neighborhood bagels, coffee, breweries, beach, playgrounds, restaurants and 15 minute walk to the Old Port & Downtown. Ample/free street parking available. Our family of four lives upstairs, our home is surrounded by flower gardens and located on the Portland Trail system. We welcome all folks of all backgrounds to our home and neighborhood!

Old Port Penthouse Suite - Amazing Harbor Views

CO2024-01992 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.

Central Arts District Studio with Free Parking

2026 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! Free off-street parking for one car available.

Downtown Apartment w/ Parking - Come Work or Play!

Whether traveling for work or pleasure, our apartment is the perfect spot to call home in the heart of downtown Portland. It's steps from the Merrill Auditorium and 6 or less minute walk to the Old Port, One Monument Square, restaurants and shopping on Exchange Street, and the Courthouse. Features of the 1st-floor apartment include off-street parking, work space, cozy living room with TV, and coffee bar.

Bright & Sunny West End Apartment.

This sunny 3rd-floor apartment is in a historic row house that was built in 1835. With the Portland Museum of Art and the State Theater a 5-minute walk away & the Old Port just 15, this home is 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.

Cityscape Loft. Central Location

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.