Holiday houses in Old Port District

Retro, in-town Apt-walk to old port, waterfront

Spacious, vintage 1 bedroom apartment w/living room, eat-in kitchen and bath, in ideal location-walk to all downtown dining, old port shopping, waterfront, ferry. West end, beautiful, historic neighborhood-watch exquisite sunsets at the western promenade. 2nd floor apartment in a 3 unit Victorian building on dead end, quiet, street , blocks from downtown. Queen size bed, full kitchen, bath, living room. Street parking is easy to come by. Note, steep flight of steps, no tv License#STHR0011152019

West End Artist's Getaway

Listed as one of the best Airbnb’s in Portland by Condé Nast, this wonderful artist's West End private suite is within walking distance of downtown, the best coffee shops, and dozens of restaurants. Filled with light and personal touches, this suite offers a private entrance, eat-in fully stocked kitchen, a large and sunny bedroom, and a full bathroom with antique claw foot tub perfect for a relaxing soak. A whole house water filter makes tap and shower water pure. License # STHR-003865-2021

Spacious Arts District Studio with Free Parking

Enjoy the quieter end of Oak Street in a historic building in the heart of Portland’s Arts District. Dining, shopping, entertainment, galleries, live music and more is just steps outside your door! This convenient and spacious studio is great for couples, solo adventurers and business travelers. Walk to just about everything the Portland Peninsula has to offer! Free parking for one vehicle is provided in a nearby lot. Come & go as you please. City of Portland 2026 registration STHR 000854

Luxury Condo in Downtown Portland Old Port

Luxury Condo in the heart of Portland's Old Port. Enjoy your stay on a beautiful historical street tucked away just steps from many restaurants, the art museum, state theater, and many other things downtown Portland has to offer! Well furnished and very clean. Every part of the rental is well utilized. Kitchen table can fold away when not in use, and features built in closets and cabinets. A true gem in the heart of the city, whether you are here to escape, explore, or on business.

Captain’s Quarters | West End • Patio • Parking

Welcome to Captain’s Quarters! Experience Portland's historic West End in this nautical-chic apartment. Great space for a weekend getaway or extended work-from-wherever stay. 🛏️ Studio apartment, queen bed 📍 Central peninsula, historic West End 🚘 Parking (off-street) 🍴 Full Kitchen 🔥 Courtyard 🏠 2nd-floor unit 💻 WiFi (1 GB) 📺 TV 👩‍🍳 Steps from Tandem, State Theatre, Chaval & more 🦞 Short walk to Downtown, Arts District, Old Port & East End ⛱️ Quick drive to several beaches

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.

Mary J. Eastburn House-Eastburn Suite

City of Portland Reg. No. : STHR-002888-2021 Perched on a quiet street corner on Portland's Western Promenade, this historic residence enjoys what Longfellow called the "rarefied air of this little town by the sea," spectacular sunsets, and commanding views of the White Mountains. Built in 1891, the Mary J. Eastburn House now offers 3 private and exclusive guest suites for those who enjoy the grandeur of the past, updated with the luxuries and technology of the present.

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.

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, Lookin Good Laundromat, and Walgreen's are steps away. Walking distance to Eventide, Honey Paw, Duck Fat, LB Kitchen, Washington Ave Breweries and Distilleries and Old Port shopping district.

Downtown Historical Victorian 2 BR APT

The West End is one of Portland's most historical districts. The house is within walking distance of Long Fellow Square, and the Western Promenade. It is a great home base while exploring. From its rich history rooted in the Victorian era, to its parks and restaurants, Portland's West End is consistently ranked as a favorite local hotspot. New reno located on a popular street in a neighborhood filled with historic homes.

Beautiful West End studio, hot tub, free parking

Charming, comfortable, well-appointed studio, 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.

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.