Holiday rentals in Old Port

Urban Seaside Retreat- East End Overlook Casco Bay

A very special retreat. Elegant and cozy, two-level, private entrance, with front row view of Casco Bay islands, parks, and easy access to the best of Portland's city life. Watch the Sun and Moon rise over the islands from this Victorian stable apartment. Walk to Portland's finest cultural and culinary offerings, to the beach for kayaking, the park for tennis, enjoy shore front trails, take a ferry to the islands. Everything to enjoy the very best of Portland is right here. (Reg.#001171-2019)

Quiet West End Retreat - parking - 100% Non Smoker

Quiet, 2nd story sunny studio apartment in owner-occupied 4 unit building conveniently located in the historic West End residential neighborhood. It’s a short walk to all that Portland has to offer. Off-street parking for 1 car. Relax on the patio and soak in the summer warmth. Perfect for a single or couple traveling to the area. No complicated checkout procedures! Just leave the key in the lock on your way out and we will take care of the rest. 100% Non- smoking guests only, No Exceptions.

Small cozy downtown loft

Cozy small private loft in a brick Victorian era home in Portland’s West End. The Old Port is only a 7 min walk away. The building is by Harbor View Memorial Park, Casco Bay bridge that connects Portland with South Portland, Cape Elizabeth, Scarborough, beaches and parks. Portland was named “City of the Year” in 2018 in Bon Appetit. Please note that bathroom/ shower are small. The apartment might not be suitable for tall individuals or elderly people due to steep stairs and slanted ceiling.

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.

Downtown Penthouse Suite - Stunning Harbor Views

2023 City of Portland Registration #20182242-ST Private 1850's Old Port Penthouse w/Breathtaking Views and Complimentary Parking Nearby. 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 ferries and smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

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. 2026 City of Portland registration STHR 000854

Modern West-End 2 BR w/ Deck - Incredible Location

Airy, spacious apartment in the quiet, friendly West End. Walk to Longfellow Square in about 8 minutes and to the Old Port in about 20, with restaurants starting about 2 blocks from the apt. Two off-street parking spaces, private deck. 2nd bedroom is a loft with its own door, overlooking the main living space. Just walk out the door for your adventure and return to your home away from home in comfort, convenience and style.

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.

Coastal Penthouse - Center of Downtown Portland!

Overlooking Portland’s historic downtown rests this coastal penthouse located on the most vibrant street in the city! This one-bedroom apartment is fitted out with all of the amenities needed for a Maine vacation! Enjoy relaxing in luxury while only feet away from Portland’s most popular destinations. This penthouse is perfect for those here for business or a Maine getaway!

Cute apartment with parking

Recently renovated, comfortable one-bedroom (QUEEN bed) apartment located in the beautiful West End district right by Old Port. Off-street parking for one vehicle is included. You will be able to just park and walk to many great things that Portland has to offer and easily drive to South Portland/Cape Elizabeth. License Number: STHR-004170-2022

Lovely, East End, one bedroom apartment.

Located in the heart of Portland's East End this unit has it all. It is within two blocks of the Eastern Promenade and a 15 minute walk to downtown Portland. Private entrance, full kitchen, dining room, and queen sized bed. Enjoy all that Portland has to offer; breweries, restaurants, food trucks, museums and amazing access to Casco Bay.

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.