Bailey Island vacation rentals

Very unique home, beautiful views, quiet, everything we were looking for. We ordered Lobsters from across the street (super nice people) in the morning and they had them ready for pick up at dinner.

Great stay at Nathan’s place. Nathan was very responsive to any questions we had, and his scones are amazing. Boothbay Harbor is beautiful as well

We had a great stay at the cottage, it was the perfect size for two people. We loved going down to the water to explore tide pools and seeing the lighthouse.

We had a great stay! The house is very nice with a view of the bay and the screened in porch was an great place to be outside but away from the bugs. The surroundings are peaceful and quiet and the house had everything we needed with appropriate notes in all the right places.

Heather and Dan were super helpful during our stay when we ran into a few issues. Really friendly and their beautiful cottage was perfect for our romantic weekend getaway. Would love to stay here again!

What an awesome airbnb! The views are stunning and surroundings couldn’t have been more peaceful. The cottage itself was exceptional and had everything I needed and more. Wish I could've stayed there longer! 10/10 would recommend this place to anyone!

Loved our time here! It’s about a 40 minute drive from Portland and then 5-10 from Brunswick. The neighborhood is quiet and perfect, exactly what we needed to relax! We loved coming back from Portland and grabbing dinner and gelato in Brunswick, such a nice way to unwind from a long day. Highly recommend and would love to stay here again :)

We had an unforgettable stay at this charming oceanfront cottage! From watching bald eagles soar overhead to seeing seals swim by, the wildlife alone made it an incredible experience. On one particularly clear night, we were even lucky enough to catch the northern lights—truly magical! We also took advantage of the fully stocked kitchen. We were able to cook fresh lobster outside, which tasted even better with the stunning 180-degree ocean views as our backdrop. Nestled in a quiet neighborhood on a quaint island road, this home is the perfect getaway. The bright and open kitchen flows seamlessly into a cozy living room that leads to a large deck. We were treated to breathtaking sunrises from the living room each morning—a truly spectacular way to start the day. Whether it was sipping coffee in the morning or enjoying an evening drink, the deck was the ideal spot to soak in the peaceful surroundings. Ryan and Sharon

Beautiful location on the water with stunning views, tranquil and peaceful with plenty of osprey and bald eagle sightings (there is a nest across the bay on Pettingill Island visible from the property). The house is very well-appointed and well-decorated. Irena was very communicative and responsive, and the house directions are clear and complete. We would stay there again. Thank you!

It was our first time using Airbnb and we couldn't have been luckier to find TwinHeart TreeTop hosted by Buck and Marie. It is a very clean,quiet and comfortable place. Marie and Buck are fantastic hosts,so nice and very accommodating. The area around Small Point is magical with so many things to see and do. The private beach is spectacular,we even saw some gray seals feeding. We'd love to be able to return. Thanks again to Buck and Marie for allowing us to stay in their special place.

We loved every minute we spent in this beautiful cabin. The views were stunning and the cabin was cozy. It's a truly delightful spot.

My partner and I had a lovely stay at this home! It was beautifully decorated and the view was gorgeous, even in the fog. We especially enjoyed the cozy gas fireplace.

Perfect location views are outstanding and it is so peaceful Second time staying here and would love to come back again

We had a great stay here! The place was perfect location and in a very nice area. Very quiet and close by to a lot of things. Also, very clean!

We’d knew we’d stumbled upon something extra special after reading one excellent review after another here…and yet still hadn’t fully imagined how perfect it would all be in person. Our anniversary weekend started with the beautiful and relaxing drive out to the point where we were warmly welcomed by Deborah who had a wealth of local tips and answered our every question. Highlights: Spectacular views over the water and inviting spaces to relax in the lovely garden; the clean, relaxing, beautifully and uniquely designed studio; dinners at Enoteca Athena and Blue (Grey Havens Inn); easy hikes, notably Morse Mountain and out to the beach… But the best? Deborah. With her thoughtfully placed vases of flowers, sweet offerings and treats, and especially her contribution to the overall feeling of connection in this special part of Maine. Thank you!

The views were amazing and the place was perfect! They’ve thought of everything (beach chairs, extra linens, coffee) and the flowers and birds make the property even more lovely. I stayed with my daughter and there is privacy within the space. The beach is a five minute walk from the house. We will definitely stay again!