Holiday rentals with outdoor seating in Portland

a wonderful place to stay.

Cathy’s place was wonderful for our family stay. Lots of space to hang out, everything is super clean, and Cathy provides everything you could need. She was also very gracious when we were not out by 10 AM, thinking that checkout time was 11. We would definitely stay here again and strongly recommended. Thank you, Cathy!

We came here for a private getaway on our honeymoon and it did not disappoint. The price was a bit much, but for such a special time I felt it was worth it at the time I booked, and worth it it certainly was. beautiful, quiet, serene, it was perfect for a getaway. I would absolutely recommend, and I already have, this stay. 10/10

My family and I stayed at Michael and Naomi's home in Falmouth and we had a blast! Their home is lovely and comfortably fit 4 adults and a toddler. We visited in August and had a couple of sticky days and were so happy that they had AC units throughout the home. This allowed our toddler to nap and us to relax in comfort. Their kitchen was well stocked with various coffees, creamers and all the cookware we needed to make our meals. The home was a short walk away from Mackworth Island and a quick 5m drive to Portland. It made getting around so easy! Michael and Naomi were very responsive and flexible with our arrangements and we would absolutely stay in the future! We loved it.

Angela was a fantastic host, responding quickly to any questions. The home was nice, close to downtown, and a HUGE yard for the dogs

Stop scrolling & just book this amazing home! Randy is an excellent, gracious & very responsive host! Check-in was a breeze w/ wonderful detailed instructions for the house and region sent in advance. This house is awesome, pristine clean, beautifully decorated and outfitted. Totally turnkey set up as they thought of everything one might need to cook, relax, sleep, explore and enjoy your visit! It's very evident that these hosts want their guests to have an exceptional experience and we did! Beds were comfy along with plenty of high quality linens and supplies. We truly cannot wait to return on what will be our regular road trips to Maine! We toured Boothbay, Chebeague Island, Brunswick, Portland, Kennebunkport, Freeport and Ogunquit while we were there. Yarmouth is awesome with super friendly locals! Close by, we found Rosemont Market, Maggie Mae's Cafe and Royal River Grille convenient options among many good ones in the area. Thanks to our host for the wine & chocolate!

We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!

The host was very accommodating and responsive! The place was spotless clean and even left us a complimentary bottle of wine. Would 100% recommend staying here! Perfect size for 4 people

Enjoyed our stay so much! Nestled into a picturesque and quiet town. Super easy to get to and from Portland without having to stay in the hustle and bustle of staying directly downtown. The house itself is charming and clean. Felt like we were coming back to our own home every night after exploring Portland and the surrounding cities. Plus, the banana bread was such a sweet and thoughtful touch. 10/10 would recommend to anyone!

We needed a place for my son’s externship. Setup for a long stay and feel like home. All the amenities made for an easy tradition to have everything provided and setup beyond expectations. Super quick and kind with any questions and concerns. Would highly recommend anyone to stay at this listing. A east walk to downtown and any site seeing.

Great apartment close to many shops and restaurants. Patio is a big bonus on nice days!

Bill’s place (the Norwood Inn) was perfect for our girls weekend while we were in Portland for a wedding. Bill and Charlie were proactive in communication and helping us be aware of check-in details and other tips. The area was walkable and we enjoyed starting our mornings walking to get coffee. Ample safe parking. Nice kitchen and a great deal for the price …. Not a luxury spot as much as just amazing location and great hosts! I’d book again.

Exactly what we were looking for. Completed our Maine trip perfectly was close to everything we wanted to go do and see I would highly recommend

Upper floor apartment with two fairly steep narrow flights of stairs for access: But the climb is worth it! This is a primarily residential neighborhood, very quiet and peaceful. Yet there are restaurants and bars just a few blocks away: the James Beard award winning Zu Bakery, the Ugly Duckling cafe, Smalls, and a low-key locals’ bar down at the end of the block. Apartment was spacious, with separate sections for dining, lounging, and a small built in desk/counter for working. Bedrooms are to the rear and quiet. Mattresses were quality & the apartment’s interior was super clean. It’s a shoes-off place, which helps. We appreciated the better than average knives, pots, pans, and the small selection of basic supplies, which included a good amount of paper supplies, coffee, etc. Thanks to Glen for being such a good host! This is what Air B&B is supposed to be like!

Kate’s place was cozy and clean with lots of added amenities. It was in a great location to explore the town and easily walk to places if you wanted! Definitely would recommend to family and friends!

Very comfortable place with lots of character. Really nice neighborhood, just a ten to fifteen minute walk from the center of Portland and the old port area. We would definitely stay here again if we come back to Portland!

Great stay

Very nice stay! The location is perfect, everything you need is on site. I recommend it!

Wonderful little spot very close to the beach. Plenty of places to walk to from the location as well as a short drive to Old Orchard Beach. Would come back in a heartbeat!

We had a great stay at Tysons place. Its a perfect location, only like 5-10 minutes drive from Old Port. The home is clean and beautiful. Street parking was super easy. Always space right on the side of the home. Each room has its own A/C. Would definitely recommend staying at Tysons place!

Great place! Close to the beach. Easy and fast communication when we needed to specify parking questions.

Great location (definitely check out Pedro’s across the street). The place was clean and well stocked with necessities. Beds were comfortable, pillows were good, curtains would have been nice due to the early sunrises.

Julie’s place was very nice and very clean. The location was great, right across the street from the ocean. The kitchen was well-equipped and there was even a small basket of treats. Julie responded very quickly to any messages we sent. We would highly recommend this place.

We loved our stay! The space is beautiful and cozy. The walk to the family friendly beach was just the right distance for my 4yo. The neighborhood is adorable and friendly! With an amazing bakery and ice cream shop just around the corner! Dave was a great host and took great care of us.