Family-friendly holiday rentals in Portland

4.97 out of 5 average rating, 531 reviews

Cozy East End 2 Bdrm. with Private Entrance

This sunny two-bedroom apartment is beautiful & spacious, located in the sought after east end, on Munjoy Hill. Just two streets away from Washington Ave., the city's newest food hub, you have access to not only a lively restaurant scene but also breweries, distilleries, a natural wine shop, a meadery and a kombuchery! The other side of Munjoy Hill, a short walk away, is the Eastern Promenade, with gorgeous views of Casco Bay, walking trails & bike paths. Walk to the Old Port and downtown.

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Flat in Parkside

4.9 out of 5 average rating, 485 reviews

Beautiful Bright Oasis - Balcony & Parking

Welcome to The Port City Oasis, an Airbnb gem in Portland! This two-bedroom apartment offers vintage charm, cozy beds, and a private balcony. Just a 5-min walk to downtown and 15 mins to the Old Port, it's in a prime location for exploring Portland's shops, cafes, and restaurants. Please note that this 3rd-floor walk-up may not be suitable for guests with mobility issues. No matter what brings you to Portland, our comfortable and inviting space provides the perfect home base for your stay!

4.98 out of 5 average rating, 184 reviews

Flat in Peaks Island

Peaks Island Master Bedroom Suite

Enjoy your stay at this conveniently located, light-filled, modern, chic living space--only a 4-minute walk from ferry, great sunsets, close to market and restaurants with a private entrance and deck. Walking distance to the best island beaches. Located on a quiet, dead end road off the main street. The space is found at the rear of one of Peaks Island's most beautiful, original Cape homes. Guests can enjoy a comfy queen size bed, organic cotton sheets, and a pull-out sofa bed.

4.83 out of 5 average rating, 107 reviews

Flat in West End

A Retreat with Spa-like Bathroom

Enjoy this large studio with great natural light, spa bathroom, comfy bed, located within walking distance to downtown and neighborhood restaurants. The eat-in kitchen is great to cook at home after a trip to the farmer's market. The main room is large. In addition to the comfy queen bed there is a desk and seating area. Look out at the park across the street; better yet-get out there. The bathroom is a fully tiled wet-room and has 2 shower heads. A great place to wind down.

4.92 out of 5 average rating, 498 reviews

Historic Munjoy Hill Retreat-Rooftop Water Views.

This stunning one-hundred-year-old home is a spacious retreat on Munjoy Hill, one of Portland's most desirable and walkable neighborhoods. Enjoy the sea breeze off Casco Bay and gorgeous views of the working waterfront from our two rooftop decks. Staying here you are just steps away from all you could want to do or dine on in our little city by the sea. Its luxurious interior and location make it a perfect getaway spot for couples or small groups of friends visiting Portland.

4.98 out of 5 average rating, 107 reviews

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!

4.92 out of 5 average rating, 289 reviews

Urban Jewel Box on Munjoy Hill

Snack and sip your way through the food mecca that is Portland, Maine from this conveniently located, newly renovated studio gem. The artfully appointed open floor plan studio is easy walking distance from the Eastern Prom, the Old Port, and Bayside breweries, allowing guests a one-of-a-kind getaway. Original wood floors are paired with exposed brick, marble, soft linens, and techy touches. Come for the lobster, stay for the lifestyle.

4.95 out of 5 average rating, 510 reviews

Tiny home in Portland

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018

4.98 out of 5 average rating, 152 reviews

Comfy Munjoy Hill Getaway with Private Entrance

Cozy, newly renovated, street level apartment on the south side of Munjoy Hill with a private entrance! This is the perfect spot for you to call home for quick visits to the peninsula and also well equipped for longer stays. Short walk to the Eastern Prom, restaurants, breweries, and everything else that Portland has to offer. Portland short term rental license number: STHR-001469-2019

Apartment in Downtown Portland

4.99 out of 5 average rating, 163 reviews

Stylish Downtown Loft – Prime Location | A/C

This stylish 1-bedroom condo is perfectly situated in the heart of Portland's vibrant Old Port, right on iconic Exchange Street. Step outside and explore award-winning restaurants, breweries, gourmet coffee shops, and unique boutiques – everything Portland has to offer is right at your doorstep! License number: STHR-006583-2024 Check-in: 3PM, Check-out: 10AM

4.99 out of 5 average rating, 134 reviews

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.