Family-friendly holiday rentals in Portland

Modern East End studio, perfect Portland home base

Enjoy all Portland has to offer from this clean and spacious studio in the city's hippest neighborhood. Walk one block to enjoy Duckfat frites at the Oxbow beer garden or head down Washington Ave for the best restaurants in Portland including Cong Tu Bot and Izakaya Minato. Walk 5 mins up Munjoy Hill to picnic on the Eastern Promenade overlooking Casco Bay or 10 mins down into the Old Port. Do it all from this beautiful and private apartment! Unit licensed through the City - STHR-006036-2024.

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)

Munjoy Hill, East End 1 BR Portland, ME

The Portland Observatory marks your way home to this apartment atop Munjoy Hill. Furnished for guests, private entrance, 1st floor unit of our 2 unit home of twenty years. BEST LOCATION! Skip the car. WALK to restaurants, music, shops, breweries, beach, parks, & historic Old Port. Stones throw to fresh produce, bakeries, wine & spirits. Furnished with LOCAL ART (made by your host in adjacent studio) the cozy apartment offers humble elegance. Just arrive, fun awaits. All are welcome here.

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.

Curated 2BR East End Retreat-Walk to Beach +Dining

Prime Munjoy Hill spot near ocean! A quick and easy walk to the Eastern Promenade park, East End Beach, and restaurants, cafes, food trucks, and breweries. Yet, our immediate vicinity is peaceful and quiet. It’s the best of both worlds. Whether you’re here to relax by the water or enjoy the local food scene, this location has it all. Only a 5 minute drive to the Old Port- or take the 30 min walk on the scenic East End trail along the water (20 min walk via the direct route).

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

*Serene* West End 2BR w/ Balcony: The Mermaid Cove

The Mermaid Cove is a bright and airy two-bedroom apartment located in Portland’s historic West End. This large private apartment is serene, yet only a few minutes walk to the center of downtown and the Old Port. Each of the two separate bedrooms are outfitted with a queen-sized Casper mattress. With a fully stocked kitchen and bathroom, separate office nook, laundry, and off-street parking, The Mermaid Cove is an easy and convenient place to call home for your visit.

Sophisticated Charm at an unbeatable price!

Apartment is centrally located to all downtown amenities and transportation system. Located in the beautiful West End on a quiet residential street approximately 1 mile from the downtown area. Apartment (3rd floor) gets beautiful sun throughout and has all of the traditional charm and character of the West End homes but updated bathroom and kitchen, both recently remodeled in 2017. Rental includes access to one parking space for a small to mid size vehicle. STHR-001018-2019

Cozy townhouse, fireplace, park free, walkable!

Charming 1 bedroom, 1.5 bath mini townhouse. Prime West End location walking distance to restaurants, shops, theaters, museums, Old Port, Maine Medical. Private entrance, small deck, dedicated parking spot. Kitchen features period soapstone sink, gas stove, dishwasher, pantry; cozy living room has gas fireplace and attached half bath. Bedroom, upstairs, has an attached full bath. Air conditioning in upstairs bedroom (only.) Ceiling fans in downstairs kitchen/living room.

Central-Local Studio in Vibrant Portland, Maine!

Spacious and private studio apartment, with sitting area, queen size bed, table and chairs for dinning, kitchen and full bathroom. Newly updated appliances in a well maintained building. Wood floors lend charm, while modern decor makes for a contemporary feel. This comfortable space is perfect to come back to after exploring the surrounding neighborhood. The Studio is steps away from Portland's best restaurants, shops, nightlife and more!

Downtown Penthouse Suite - Stunning Harbor Views

CO2024-01992 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.

East End Unit

Our unit is located in the East End on a quiet street just up from the waterfront. Minutes walk to the Eastern Prom, the Old Port, and many excellent restaurants and bars. Private entrance and the entire driveway is reserved for you. Free street parking. The one-time fee for EV charging is $20.