Holiday rentals with outdoor seating in Portland

This cozy and beautiful home was squeaky clean and very well organized. Our kid enjoyed going up and down the staircase. We only stayed overnight but would have loved to extend our stay if possible. Would definitely recommend!

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

We had such a cozy and comfortable stay! The space was thoughtfully stocked with everything we needed and the little touches made it feel extra welcoming. The location is also superb! Extremely walkable and close to tons of amazing restaurants. One of our favorite parts was starting each day with a walk along the Eastern Promenade which then led us to make our way into beautiful Old Port. Meredith is a wonderful host- so kind and friendly. Her pup is extra cute too. Highly recommend staying here if you’re visiting the area!

Adina’s airbnb is in an incredible location—we were able to walk to all of the restaurants we wanted to visit easily and it was only a 10-15 minute ride from the airport. The airbnb itself was perfect for my brother and I, since there is a bed and a pull-out couch that were both suitable. Adina was very good at anticipating our needs and at making sure everything was going well with our stay—she’s a wonderful host! Whenever I decide to stay in Portland again, I would be grateful to stay at her place.

Cozy place in a nice area! Walkable to downtown. Great communication - very nice and accommodating! We had a great trip :-)

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!

Dax was a very friendly, accommodating host. The place was very cute and also very clean upon arrival. We would definitely book again!

Amazing stay with everything we needed. Wonderful location and comfortable space. Would love to stay again.

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!

This cute little cottage was perfect for my stay in Old Orchard Beach. My stay was in cold January but the cottage was warm and cozy. The highlight was being steps from the beach and being able to roll out of bed and catch the sunrise each morning.

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

Great location, clean place, and very responsive hosts. We loved being within walking distance to so much!

You cannot beat the location with this rental. We love coming to Willard Beach with our pup, and when our old go-to BNB stopped renting we were so worried we wouldn’t find another. But this condo worked out so perfectly in terms of location (across the road from both Scratch Bakery and Willard Scoops, comfortable walk to the beach with several entrance options) and the actual comfort of the condo itself. The proximity to the beach was really a plus for us, as we didn’t have to get up as early to make the dog friendly beach hours! Host is responsive, and any household items (eg. soap, coffee filters) that were missing from the condo we could easily run down to get from Hannaford. The downsides: It is on a second floor walk up, which may be challenging for those with mobility issues. Hand railing is odd too. Bit pricey, couldn’t swing a full week this time around as the price shot up dramatically when I added Friday to the duration. But overall, really lovely!