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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)

Crow's Nest

Registration# 2018-4091. Watch the bustling harbor over coffee or wine on your private roof deck, walk to Portland's best restaurants, stroll the Eastern Promenade, shop your way to the heart of the Old Port...Just a taste of all that's within a short walk from the front door! You'll find more windows than walls in this airy sun-filled 'nest' in Portland's hippest neighborhood, the East End! NOTE: All guests must agree to House Rules below within 24 hrs of booking to be confirmed by host.

Charming, Minimal Apartment on Munjoy Hill

Located at the top of Munjoy Hill, our minimal, cozy, first floor apartment is the perfect Portland location - a short walk to numerous restaurants, coffee shops, breweries, the Old Port and Casco Bay Ferry Lines, and very close to the East Promenade with its ocean views, picnic spots, and trails for walking and running. Our place is good for couples, solo adventurers, small families, and business travelers. We live in the building and are usually around to answer question or help if needed.

Luxury One Bedroom Loft in Portland’s Old Port

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.

Joyful Munjoy Hill Garden Suite

Attached guest suite with private garden entrance in Portland's vibrant Munjoy Hill neighborhood. Minutes from cultural, culinary, and outdoor pursuits in Portland's Old Port and Arts District. Walk to markets, restaurants, coffee shops, breweries, bars, bakeries, shops, galleries, museums, and more. Stroll along the Eastern Promenade gazing at picturesque Casco Bay. Trails, bike path, parks, beach, SUP/kayak/bike rentals, and ferry terminal all are steps away.

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.

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

Cozy Urban Treehouse on Munjoy Hill

Snack and sip your way through the food mecca that is Portland, Maine from this conveniently located, newly renovated one bedroom retreat. The lush and transportive attic apartment is easy walking distance from the Eastern Prom, the Old Port, and Bayside breweries, allowing guests a one-of-a-kind getaway. White lacquer floors are paired with antique furnishings, soft linens, and techy touches. Come for the lobster, stay for the lifestyle.

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, king sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

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 20 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.

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.

Cozy Rock Cabin #thewaylifeshouldbe

*As seen on Magnolia Network's 'The Cabin Chronicles'* Cozy Rock Cabin is an 800 sq ft cabin on three acres of wooded land. Carefully designed for couples and digital nomads, it has everything you'll need to explore southern Maine (#thewaylifeshouldbe) or just stay cozy in front of a fire.