Family-friendly vacation rentals in Bailey Island

Lori’s is exactly what we need while visiting family over a holiday. She is very gracious to host us over Thanksgiving as the last occupants of the year. Even during a snow storm, her place is cosy and beautiful. This is our second year coming, and we love it every time. We would recommend it for those looking for a charming getaway from busy life. Thanks Lori!

Meghan's home was a perfect place to stay for my sister's Bachelorette weekend! The home is located in a quiet community with views of the river and bay, and it was conveniently located with just a short drive into the heart of Portland. We found our stay extremely comfortable, especially on such a cold and dreary April weekend. Meghan had the hottub ready for us with matching robes for all which was a fun surprise. Check in and check out were a breeze. We even took a breakfast recommendation from the guest book (Forage Market, yum!), a tasty experience indeed. Thanks again, Meghan!

We had the most amazing stay at Madawaska! Amazing views from the bedroom and hot tub in a beautiful, peaceful, and private location overlooking the water. And such a wonderful design of the cabin. We will definitely be back!

We love staying at the Brownie. It’s a great home for any active family that appreciates a quiet surrounding. Great home and so close to SR. It can’t be beat.

This house has a beautiful location super close to the beach and a close walk to restaurants and activities. It has great views and plenty of room for a large group! Check in was super easy and they greeted us and went through everything so clearly that we knew where everything was and how to use it all - which was very helpful with such a big place with so many amenities. The hosts were communicative and helpful leading up to our stay and again with check out. The house itself is stunning with everything stocked for your stay. The only thing to be aware of is that there is a train that runs close by so definitely bring your sound machine. Would definitely rent this place again!

Great place. The bed was really comfortable. Hot tub was nice and private and relaxing.

Paul's house was wonderful! It smelled so fresh when we arrived and was very clean. The house was more spacious than i expected. It was just us two of but could absolutely fit another couple and a few kids with plenty of privacy. We really enjoyed fires in the wood stove with firewood provided. The soaks in the hot tub were amazing! The beach towels were greatly appreciated for wrapping up in to hurry in from the cold! We had fun grilling in the snow and found everything we needed in the kitchen. We felt right at home. Our dog had a blast playing in the big backyard too! Paul has great communication and was very fast to respond. Paul's vacation home is perfect place to relax and unwind! Thank you for sharing your beautiful Maine getaway Paul!

Gorgeous grounds and location for a quiet peaceful weekend getaway! David was very responsive and personable. The cabin is eclectic with something new and interesting in every corner.

This home is amazing! It was perfect for our group of ten family members that were in the area to celebrate a wedding for the weekend. Our hosts could not have been more accommodating and we were so impressed with their hospitality!! So many nice touches and such a spacious, comfortable home - no detail overlooked. Enjoyed our stay immensely and would definitely return.

Cozy and comfortable place to stay while exploring the area. Close to most anything you’d want to do in Southern Maine.

Absolutely love this place! The life of the brewery and the community is simply unmatched :) the hosts were warm, friendly and super responsive

We had a wonderful stay at this Maine house--Barb, the property manager was incredibly responsive, helped with a heating issue while we were there and had the repairs done same day--The house was well equipped with everything you need for a family getaway at the beach! puzzles and games galore, kitchen was fully stocked with everything needed for family meals (including lobster cooking essentials--bibs, crackers, steam pots) Great little fire pit out front which we enjoyed, and fenced in back yard area so pets or kids can be safely contained :) Linens, towels, all clean and provided--truly a wonderful home away from home, perfect for our family trip to the beach!

We loved our stay at Katie's house in Portland. It was very comfortable, clean and nicely decorated. We would love to stay again soon!

A group of 5 of us stayed at Kathy's listing and felt like we had plenty of room. We were all comfortable and found the location to be great with plenty to do within walking distance. Some of the doors were glass with blinds/shades that weren't entirely opaque so we had to be somewhat mindful when changing in our room. The front door battery was dead when we arrived and so the door was unlocked but this was quickly resolved with the help of the host and extra batteries on site. Location was fabulous and peaceful. No issues with finding free street parking, either. Overall, we enjoyed our time here and would stay at this listing again!

Great retreat to feel relaxed and inspired. The location suits our needs for comfort and accessibility to surrounding disc golf courses and is great for travelers looking to escape screens, and the stress of cluttered and busy lifestyles. It feels like home as soon as you arrive .

I have stayed at Anne’s place many times. Anne and her husband are always very nice and friendly. The apartment is spotless, comfortable and you can’t beat the location, just up the hill from charming Falmouth Town Landing and beach and an easy drive to downtown Portland.

100 percent recommended!!

Great place to stay in Ogunquit area! The cottage is exactly as described, and well located between Wells and Ogunquit - you do need a car to get around easily as others have said. This is a fantastic place to stay with kids - having the pool facilities especially is great as a break from the beach. Julie and Derek left great advice as well as flexibility on check-in - thanks again!

Great home for our large family gathering. Great location near Sunday River skiing, Downtown and snowmobile trails right outside the door. We had a great time and will be back.

Was a very nice peaceful getaway the home was spotless and had everything we needed plus extra great place to disconnect

No frills but perfect for what we needed. Easy ski in and ski out. Kitchen is a bit tight and very little cooking stuff but otherwise comfortable and great for a ski weekend

A good ski in ski out location. Perfect for us. Thank you.

We absolutely loved our visit to Appledore Cottage! It was quaint and perfectly relaxing. The screened in porch was the best place to just sit…very quiet and peaceful!