Kid-friendly holiday rentals in Portland

the perfect cabin nestled in the woods in a quaint town! We spent the week in Emily’s peaceful cabin and it was the perfect Maine getaway. The pond is a highlight! I loved getting to stay in this lovely cabin.

We stayed at Kathleen’s charming place in and had a wonderful experience. The space had everything we needed and was also perfect for my husband and me to work remotely. I worked from the second bedroom with the daybed, while my husband set up downstairs. The location is within walking distance to everything, and Kathleen gave us some great local recommendations. We’d love to stay again!

Great location on the east end--residential with short walk to the Eastern Promenade and large waterfront park, as well as downtown and tourist amenities. Very efficient use of the small space. Because we wanted to take advantage of dining out, the lack of a kitchen was no problem for us. The bedroom was surprisingly large and bathroom a tad small, but overall a very homey and comfortable stay for a few days.

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.

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!

Stayed here for 1 night to cap off a Maine coastal trip and it was a perfect place to unwind and relax. Good walkable food options and very comfortable bed.

I can’t say enough about what a nicely appointed home in a beautiful setting this is. I came for peace and tranquility and it did not disappoint. I haven’t had such good sleep in over 2 years. Highly recommend and plan to return next year! Thank you all so much for sharing your lovely home.

The upstairs apartment was perfect for our stay in Portland. It’s clean, cozy, and a great location. We really enjoyed our stay and recommend it.

Great location close to downtown Portland. Lots of walkable places close by for coffee and breakfast. A little farther to some unique restaurants. We Uber'd a lot which worked out great to avoid parking around Portland. We would definitely secure this nice place the next time we come to Portland!

We absolutely loved our stay. This was our first time in Portland and coming back to this unit after a full day of activities felt like we were right at home. Lucie has truly made this unit so warm and inviting with great attention to detail. The location itself is also great, not too far from the city to drive but not too close either. Thanks again!

We absolutely loved our stay here. Extremely clean, great shower, super comfy bed and location was great for our weekend exploring Portland. Would definitely stay again!

This was my second stay at Scott‘s amazing penthouse. So beautiful and comfortable and clean and you can’t beat the views across the harbor. I really needed a break and loved the comfortable beds! Just as described. Close to restaurants, shops and waterfront. The proximity to everything and the parking so close by made for a relaxing weekend. Scott was always immediately responsive when I had a question. I hope to be back for a third time in the future.

First time in Portland and this apartment was perfect for two people. Comfortable bed, clean kitchen. We did not have a car and did not need one to get around downtown. Literally five minutes to the harbor and so many great restaurants. Would absolutely stay there again.

Nice town home in the West end of Portland. Easy walking distance to a lot of restaurants and attractions. Host was very nice and responsive, and check instructions were very easy. The unit comes with some wonderful personal touches and basic supplies like snacks, wine, coffee, butter etc... The neighborhood felt safe, the building is an older building so you will hear neighbors walking around upstairs. Parking is tight on the streets but there is supplied parking in back. We found the parking to the left of the building to be too tight even with our small rental, but luckily the spaces in the back were always available. The unit is spacious, with a living room, kitchen, and separate bedroom. Although the bathroom is very tight, especially around the toilet, and could be an issue for a plus size person. The host was nice enough to leave us a bottle of wine and a wonderful welcome sign. Would definitely stay again.

The unit is rustic, will not be to everyone's taste, but it's unusually spacious and tucked away from all traffic noise, not to mention walking distance from downtown and the Old Port. Lots of places to eat! Easy to find a parking spot on the street. All we ever heard from outside were children playing and birds. The stairs are steep, so not advised for those not fit or who have balance issues, and it takes awhile for the heat to warm up the place on colder nights (though it does get there). But Sharon is responsive and accommodating. We enjoyed her little perks like Swedish Fish.

Great stay! Location is perfect for everything we wanted to do, be by the water, stay right next to downtown, and a short walk from our tour with Eco Adventures. Furniture was very comfortable and everything was clean. Great restaurants in the area. Would return back!

Great stay

Beautiful, spacious and bright house, with everything you need to be comfortable and explore Portland. At one point, we had a problem with the fire alarm and Allyson not only answered in minutes, but also told us how to fix the problem and left us extra batteries so it wouldn't happen again. Don't hesitate to stay at Allyson's, not only is it the ideal accommodation for a family, but Allyson was the best host. Thank you very much!

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!

Loved my stay! Jason and Steve were great hosts, and super responsive. it was great getting to bring our dog too! I would stay here again.

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

The Baxter Suite was perfect for our weekend stay with 4 people. Thomas was a great host- very responsive and accommodating. The apartment is beautiful and very clean. The bathroom is gorgeous and beds were so comfy. One note is that the only mirror is in the bathroom and there is no full length mirror (not a huge issue but a small struggle with 4 women trying to get ready at the same time lol). The free parking spot was very nice to have but there was also plenty of street parking available. Overall Thomas’s place had everything we needed and we would stay here again!

We stayed at a few of Spencer's places while our child was at Bowdoin college. The places are lovely and convenient and made visiting our child a pleasure.

We enjoyed our stay at this Airbnb! The location allowed us to walk to most every where. There are a few gyms near by that have day passes. The kitchen was spacious and bathroom quite large. I loved the fact that there was a huge supply of sheets, towels, pillows etc. Plenty of hot water for everyone to shower. The queen bed was comfortable. The feedback about the couch from our children is that it’s more comfortable to sleep on as a couch than pull out bed. There is natural light and great wall unit ACs that made our stay comfortable. It’s very quiet inside given that it’s on a busy street. We had a really fun long weekend and highly recommend!