Vacation rentals in Old Port

RETRO BnB in the Heart of East End Portland

Retro BnB in The Heart of Portland's East End offers a combination of 70's mod charm with a vibrant comfortable style. Sunny, first floor back apartment with private entrance, one hybrid coil/thermarest queen bed overlooking yard with lovely perennial garden, bathroom with central, well appointed kitchen/dining room. This space is perfect for one couples looking for a cozy home base hideaway. A short walk to gourmet restaurants, cafes, East End beach and all Portland peninsula has to offer!

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.

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.

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.

Boutique Space * Steps to Eastern Prom * W/Parking

Beautifully appointed 1BR in Portland's quiet, coveted East End. Just a short walk to the Eastern Prom and Old Port restaurants. This first-floor apartment features a modern vibe, local artwork, Brooklinen linens, luxury towels, hotel-level cleanliness, and local coffee. Freshly updated with new finishes in Jan 2026. Quiet owner-occupied building with off-street parking, outdoor shared patio, grill and gas firepit. Queen bed + queen sleeper sofa. Non-smoking, no pets.

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!

Walk-able Portland Studio

NEWLY RENOVATED! Cozy studio apartment in a historic building, located in Portland's East End Neighborhood. This location can't be beat! The Space features original hardwood floors, and large windows, subway tiled shower and thoughtful decor. Portland Food Co-Op is directly next door, as is the Walgreen's. Walking distance to Eventide, Honey Paw, Duck Fat, Hugos, Little Woodfords, LB Kitchen, Washington Ave Breweries and Distilleries and Old Port shopping district.

Modern Studio Loft w/ Parking in Perfect Location

This spacious and comfortable studio loft is in a historic building in the heart of Portland's Arts District, where dining, shopping, entertainment, galleries, live music and more is just steps outside your door! Located on the quieter end of Oak Street, the studio is within walking distance of everything Portland's peninsula has to offer. Free parking for one car is provided in a nearby lot. 2025 City of Portland registration STHR 000854

Old Port on foot

Newly renovated, spacious and modern top-floor condo in a posh historic building in the heart of downtown Portland. Leave your car behind! Walking distance to tons of bars/restaurants, stores, a block from the Portland Harbor/Commercial St and 3 blocks from Merrill Auditorium. Please note there is an additional $50 cleaning charge for stays greater than 7 nights. For stays greater than 14 nights, the cleaning fee is $180.

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.

Chic Portland Penthouse, 2BR

Enjoy a stylish experience at this centrally-located place. We are in the middle of all the excitement in the Old Port. Ride down the elevator and just out our front door you are steps to all the best that Portland has to offer. Shops, dining and night life all conveniently at your door step.

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.