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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.

Luxury Year-round Treehouse with private hot tub

Skyframe is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

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.

Charming 1st Floor Flat by the Prom

1st floor renovated 1890 3-bed apartment ready for gatherings! Walking distance to restaurants, bars, breweries & plenty of shopping! Located 2 blocks from Eastern Prom, beaches and walking paths. Taxi ride to downtown Street parking only, but typically easy and free! Apartment living, some noise. Building is Owner Occupied and has long term tenants. Please be respectful, and no loud parties! A/C installed first week of June to last week of Sept. License #STHR-001107-2019

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!

Parkside Retreat on Portland's Eastern Promenade

This one-bedroom, first-floor apartment located on the Eastern Promenade - across the street from beautiful Casco Bay and central to the Old Port and West Bayside communities. The neighborhood is full of recreational and dining opportunities with the 88-acre park and trail system, restaurants, sandy beach, waterfront playground, kayak rentals, tennis and basketball courts, etc.

HotTub+Firepit/5 min to DockSquare, Dining, Beach

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."