Family-friendly holiday rentals in Portland

Sometimes photos just don't do the real thing justice, and this is the case with this property. The property and the views are truly spectacular! The home is huge and has everything you could ever need to live for a week or more. The porch, especially the screened in portion are magnificent and the hot tub was a perfect way to finish up a great day. We had so many plans to adventure out, but found ourselves wanting to stay and enjoy the pristine yard or just sit on the porch and enjoy each others company, we didn't want or need to leave. Having coffee and watching eagles fly by over the river was truly spectacular. Judy is one of the nicest, easiest hosts we have had the pleasure to work with and truly appreciates your patronage. And Hugh's journal on all things Graywood is a lifesaver. Not only would we return again, but we look forward to it.

David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.

Beautiful spot to stay at, we didn’t get so lucky with how weather panned out but it didn’t take away from the experience we had. Would recommend to anyone!

A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.

The house was beautiful and worked perfectly for our group! Check in was very easy, and the house was spotless when we arrived. My favorite part it was the yard - perfect for a big barbecue with a large group.

Nice stay, nice host, lots of recommendations in binder for things to do. Nice hot tub. Cozy place and location. DQ right across the street.

Jon’s cabin is a beautiful place to get away from it all. Very comfortable and well designed. We had everything we needed to cook and hole up for a few days. If you decide to drive to the lake, I would recommend 4WD. We had a truck but were not aware of how soft the ground was and ended up needing to be towed out. Still highly recommend! Enjoy your stay!

The spot was perfect for a weekend of skiing and riding snowmobiles. Exactly what we were looking for in a vacation home. Paul was great at recommending places and his response time was great. Also the wood burning stove made the weekend cozy and perfect.

We have stayed at Jackies place twice now and enjoyed it just as much this time as the last. Even though it rained for two days the house is plenty big enough to spread out. We had to change our reservation days twice because of circumstances and Jackie was very accomidating..

We had an absolutely beautiful, special, memorable and meaningful stay here, and immediately started plotting how to get back asap on our ride home. Naughty Dog Island is breathtaking, so incredibly peaceful, is a magical world all in it's own, and wow Kent has really figured it all out. Everything is so well thought out, from the nature of off-grid living to the peaceful hang out spots, the impressive communication making sure we had everything we needed, and with immediate response to any questions, we felt right at home and cared for in the best possible way. Kent and Heather went way above above and beyond for us, and were the kindest, sweetest, and most thoughtful hosts. The house was so comfortable and the island just gorgeous. Super easy and flexible check in/out and logistics of getting to and from. I can't say enough good things about this absolute gem of a place. I highly recommend a stay here, and promise you will never want to leave. Thank you Kent + Heather!!!!!

Thoughtfully designed and appointed place - has all the things you need and Marcia makes it very easy to get in and check out. Easy to get to Lewiston, Brunswick, Portland and everywhere in between!

Very clean, great location in Portland. Street parking was a bit challenging but doable!

Can’t say enough about how great our stay was! Andrew was incredibly responsive, let us check in early and check out late without even asking. It was a great location on the island, very walkable, even for my mother with a bad knee (she was exhausted after the first day though). Would absolutely stay again!! 10/10

A beautiful and cozy space with lovely natural light and generous room to spread out. The full kitchen is equipped like a real home, with everything from basic pots and pans to whisks and even nut crackers! A great place for cooking full meals. A nice quiet location, even with its relative proximity to a regularly-traveled road. I'm sensitive to noise and was never bothered by sounds of traffic. Pettengill Farm is only a few minutes up the road, a beautiful place to walk for both dogs and humans and really easy to access multiple times a day. Mandana was always very responsive to communication, and when there was a glitch with Airbnb's fee calculation she was extremely helpful and approachable and took care of it immediately.

This home was fabulous! The space was clean, lovely, and so comfortable. Additionally the neighborhood offered but walks in nature and restaurants/stores. I wish I could go back next month!

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.

Our stay at the beach house was great! You couldn't be closer to the water! So much fun kayaking, floating and swimming in the lake! House is much better than the pictures do it justice. For a 2 bedroom house its very big and spacious, beds were extremely comfortable. The no wifi was a little bit of a downer but there were plenty of board games to play. There is some street noise but not bad at all. Would most definitely recommend if you are looking for waterfront property. The access to the resort pool was a plus too for the kiddos!

This place had everything we needed. The view was spectacular! We really enjoyed seeing fireworks from the deck. The home was very clean, kitchen fully stocked. We loved hearing live music each day and night. So much walkable fun for the kids. We had a wonderful stay!

Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

Perfect little spot on Frye Island! Great location, walking distance to our favorite beach on island as well as the general store. House was clean, comfortable, just as described. We enjoyed our stay!

Maryann is SUCH a treasure! She really is the hostess with the mostest! Gives great recommendations, homemade coffee and treats, and if you mention you like something, she might get it for you! Making this Philly girl a wannabe Maine resident! Couldn’t recommend more.

Home is very expansive with room for multiple families to reside together. Lots of games and activities for all ages. Amazing location within minutes to airport and short drive to downtown

My family and I had a awesome time enjoyed the quiet and relaxing days. Michael was very helpful and very quick responses to any questions we had.The cabin was very nice it felt like home was very comfortable slept very well. Everything about the cabin and the island was well worth going looking forward to going again in the future.

We had a great time at Jim and Gwens place in Knight's Hill. The amenities were great and the location provided us with everything we were looking for near Moose Pond. Would highly recommend.