Holiday houses in Old Port District

A bright living area is illuminated by natural light, featuring large arching windows draped with soft curtains. A comfortable sectional sofa is paired with a modern accent chair, and a round coffee table centers the space, anchored by a textured area rug.

4.96 out of 5 average rating, 104 reviews

Luxurious Two Bedroom Loft Adorned with Local Art

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.

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4.97 out of 5 average rating, 301 reviews

Cottage in Portland

4br2ba House+parking@PeacefulOasis on Munjoy Hill

This standalone 1500sf 3-story cottage is set in an ideal location, close to the Eastern Prom, cafes, award-winning restaurants, breweries and the Old Port. -Main floor: well-equipped kitchen + open concept living/dining room -Upper floor: 3BR (1 queen, 1 full, 1 twin) + bath -Garden level: 1BR/1 bath (queen) with private entrance - Off-street parking for 1 car This charming home @ A Peaceful Oasis offers plenty of space, privacy & comfort, making it the perfect home base for your stay.

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Condo in Downtown Portland

The kitchen features modern stainless steel appliances, including a range and microwave. Granite countertops provide ample workspace, along with white cabinets for storage. A coffee maker and various utensils are neatly arranged, contributing to a functional and well-equipped cooking area.

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.

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4.88 out of 5 average rating, 534 reviews

4.99 out of 5 average rating, 153 reviews

An open dining area features a round wooden table surrounded by blue chairs. A comfortable living room area is visible, with a gray sofa and art on the walls. Large windows allow natural light to brighten the space, enhancing the modern design.

Apartment in Portland

Harborview - Curated East End Escape w/ Parking

Harborview is a newly renovated, top-floor apartment perched on the edge of Munjoy Hill in Portland's East End. This home is a short stroll to the Eastern Promenade and the East End Beach, the Casco Bay Islands Ferry Terminal, and the historic Old Port. The apartment features a spacious open kitchen, dining, and living room floor plan adjoined by a large private deck. It's the perfect spot to gather, relax, and dine while enjoying the breathtaking views of Casco Bay!

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4.97 out of 5 average rating, 517 reviews

A common area is depicted, featuring a spacious couch adorned with yellow pillows. A light wood coffee table is centered on a striped rug. Natural light flows through large windows, illuminating a dining table with several wooden chairs, complemented by a cozy décor.

Apartment in Portland

Bright and cozy Munjoy Hill neighborhood apartment

Bright and cozy apartment in Portland's Munjoy Hill neighborhood with private backyard deck. Short walk (like a minute!) to neighborhood bagels, coffee, breweries, beach, playgrounds, restaurants and 15 minute walk to the Old Port & Downtown. Ample/free street parking available. Our family of four lives upstairs, our home is surrounded by flower gardens and located on the Portland Trail system. We welcome all folks of all backgrounds to our home and neighborhood!

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A modern lounge area is highlighted by large skylights, allowing abundant natural light to fill the space. A sleek, white sectional is complemented by colorful accent pillows and a patterned area rug. Exposed brick walls add an element of rustic charm, with scenic views of the harbor visible through the glass.

4.97 out of 5 average rating, 327 reviews

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.

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Loft in Downtown Portland

An urban scene in Portland's Arts District features historic brick buildings with large windows. Colorful banners showcasing art design hang from lamp posts, while greenery from nearby trees adds a vibrant touch. The image captures the local atmosphere, highlighting the blend of culture and community.

Central Arts District Studio with Free Parking

2026 City of Portland registration STHR 000854 Enjoy the quieter end of Oak Street in the heart of Portland's Arts District. Abundant dining, shopping, galleries and museums are steps from this home-away-from-home studio apartment. This is a perfect space for couples, solo adventurers and business travelers. Easily walk to everything the peninsula has to offer from this centrally located studio apartment! Free off-street parking for one car available.

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4.94 out of 5 average rating, 772 reviews

A spacious living area features exposed brick walls and large windows, providing ample natural light. A comfortable sofa and two accent chairs are arranged around a stylish coffee table. A chandelier hangs above, and a television is positioned on a console in view.

4.91 out of 5 average rating, 64 reviews

Old Port Loft - 301

Discover the charm of Portland, Maine, from the comfort of our elegant 3rd-floor unit located in the heart of the Old Port. Steps from Portland’s vibrant nightlife, offering unmatched energy—but expect the buzz of the city late into the night (especially in the summer months when there is live music and outdoor dining just outside the building). Sound machines and earplugs are provided for guests comfort. Maine Lodging License #32635

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Superhost

The exterior of a three-story building is shown, featuring light green siding and multiple windows with shutters. Two trees are located in front, providing shade. The area is lined with a sidewalk and parked cars, contributing to the accessible downtown environment.

4.77 out of 5 average rating, 604 reviews

Downtown Apartment w/ Parking - Come Work or Play!

Whether traveling for work or pleasure, our apartment is the perfect spot to call home in the heart of downtown Portland. It's steps from the Merrill Auditorium and 6 or less minute walk to the Old Port, One Monument Square, restaurants and shopping on Exchange Street, and the Courthouse. Features of the 1st-floor apartment include off-street parking, work space, cozy living room with TV, and coffee bar.

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A bright living room is illuminated by sunlight streaming through large windows. A round dining table with white chairs is set near a cozy seating area featuring a patterned sofa and decorative cushions. Built-in shelves display books and decorative items, complemented by warm wooden accents.

4.94 out of 5 average rating, 627 reviews

Bright & Sunny West End Apartment.

This sunny 3rd-floor apartment is in a historic row house that was built in 1835. With the Portland Museum of Art and the State Theater a 5-minute walk away & the Old Port just 15, this home is steps from the best eateries, arts and shopping the city has to offer! When you arrive, park your car in your private spot behind the house and forget about it for a while.

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Superhost

A spacious living area features large windows that provide cityscape views. Two leather sofas and a glass coffee table are arranged around warm hardwood flooring, while a lamp adds soft lighting. Natural light illuminates the room, creating a bright and airy ambiance.

4.79 out of 5 average rating, 674 reviews

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.

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