Vacation rentals in Old Port District

Quiet, eco-modern apartment with parking and decks

Bright, eco-friendly apartment on a quiet street in Portland's trendy East End. Modern style amenities, master suite w/ heated bath floor, in-unit laundry, hardwood floors, efficient heat/AC, well-appointed kitchen, two decks, and 1 off-street parking space. Beds are soft with 100% cotton sheets and hypoallergenic pillow covers. Non-toxic bath & cleaning supplies. Air purifiers in living rooms. Note: Bedrooms on 3 levels, stairs steep, & 3rd bedroom in semi-finished basement with no bathroom.

Family · Location · Air conditioning

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.

Value · Family · Comfort

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.

Value · Family · Bathroom

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.

Location · Value · Wifi

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!

Location · Family · Parks

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!

Family · Location · Bathroom

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.

Value · Location · Hospitality

3 bedroom house in the heart of Portland

New urban 2000 sq ft home in Portland's vibrant up and coming East End/ Munjoy Hill neighborhood. Mid-century style decor. Open concept kitchen/dining/ living area, 3 spacious bedrooms plus a quiet office/study. 2 balconies with views west to Back Cove. 2 car garage and plenty of free off street parking. There are restaurants and bars with great food and live music close by. There is a convenience store around the corner for any last minute needs.

Value · Family · Indoor spaces

Sunny Arts Dist. Studio- Queen Bed & FREE Parking

A clean bright studio in a historic building in the heart of Portland’s vibrant Arts District where dining, shopping, entertainment, galleries, live music and more is just steps outside your door! Walk everywhere on the peninsula from this convenient and central studio with a full kitchen, lots of natural light and an extra sleeping loft. Free parking for one vehicle provided across the street. 2026 City of Portland registration STHR 008545

Value · Location · Check-in

Walk to Top Dining • Boutique Stay • Parking

This beautifully renovated, light-filled apartment offers a rare mix of space, comfort, and walkability. Guests describe it as spotless, spacious, modern, and exactly as advertised—an easy, relaxing stay from booking to check-out. • 150+ five-star reviews • Guests return again and again • Dedicated parking spot • Everything you need for a seamless stay

Value · Family · Comfort

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.

Value · Family · Decor

Modern Condo Portland's Historic Old Port District

Enjoy a stylish experience at this centrally-located loft. A converted factory building has been transformed into this chic and modern condo. Cobblestone streets, endless incredible dining and nightlife, boutiques, shops and historic architecture. A quintessential New England seacoast town and working waterfront.

Family · Value · Long stay