Holiday rentals with outdoor seating in Bailey Island

a wonderful place to stay.

Perfect weekend retreat for a small family with a young one. Close to downtown, museum, and the firepit was so nice at night. 5 stars all around and will return in the future. Thanks Phillip!

Jeffrey’s guest house is super special, it was amazing to be able to look out every window to experience coastal Maine and so serene and peaceful. Located on a beautiful property right on the bay in a wooded setting. Very private and quiet. We absolutely loved our stay - in fact we extended it another 3 days to be able to enjoy it longer. Jeffrey was very accommodating and even credited us for the 2nd cleaning fee charged by Airbnb because we needed to change our payment method for the extended stay. I can’t say enough about the comfy bed!! I felt like I was sleeping in a cloud with super soft sheets and perfect mattress. I wish all Airbnb hosts were as thoughtful about the personal touches as Jeffrey. I had to work a bit during the trip and the internet was very stable and easy to connect to. It was a perfect retreat for us. Highly recommend staying here! We will. Definitely will Return!

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

Thoroughly enjoyed our stay! We unexpectedly had beautiful cloudless days most of the week. Great location & easy to get to the Harbor and Southport both of which we enjoyed! Recommend the Carriage House for a really top quality meal as well as Blue Moon Cafe (good lobster roll) which was one of Shirin’s recommendations. Would totally stay here again!!

We loved our time staying here, the house was beautiful and just as described/ seen in the pictures. Randy was a great host and always very responsive with some great local recommendations. Would definitely love to return!

We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!

This is such a beautiful space! Very cozy and tucked away in a residential area. The home felt safe and was very close to downtown Freeport, where there are great options for food/beverage and shopping.

Enjoyed our stay so much! Nestled into a picturesque and quiet town. Super easy to get to and from Portland without having to stay in the hustle and bustle of staying directly downtown. The house itself is charming and clean. Felt like we were coming back to our own home every night after exploring Portland and the surrounding cities. Plus, the banana bread was such a sweet and thoughtful touch. 10/10 would recommend to anyone!

Cute place! I enjoyed my stay. The hot tub was hot when I arrived, which I didn’t expect but highly appreciated!

We had a great stay. The location is quiet but just a few minutes away from amazing restaurants, cafes, and breweries. Highlights: The bed was super comfortable. The sauna was great on a rainy day. The walkability to the Back Bay trail was appreciated.

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!

This was our second stay with Emily in less than a month. Just as comfortable and convenient as the first time. We hope to book her space again for the holidays this year.

I had an amazing stay! Rachael was a very responsive host, and was very helpful throughout my stay. The location was quiet but within driving distance of all the things I wanted to do, and it matched all my expectations based on the listing. If I’m ever back in the area, I would certainly love to stay here again!

A lovely place to stay in Portland’s East End. Great location in a very quiet and walkable neighborhood. (I happily did not need a car during my visit.) The apartment is great, with a comfy bed, smart TV and a nice little patio too. And you’re just steps from the Eastern Promenade park, which is one of Portland’s best amenities imo and leads to a beach, waterfront trail, dock w/ kayak rentals, etc. Jennifer was a very kind host; thank you!

Our stay at The Bee Keepers Cottage was amazing. The property met our needs perfectly and it was super cute and cozy. The host was very responsive and communicative. And for any star gazers out there, the sky on a clear night is mesmerizing.

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!

Great place to stay if you want to be close to downtown but with a larger, comfortable space. The place is exactly as described, exceptionally clean and tastefully decorated. No dollar store products here! The ground coffee and half and half really made it feel like we were staying at a friend’s home.

We had a great time! The condo is clean, cozy, and comfortable. I highly recommend this AirBnB, especially for the beach proximity.

Great location (definitely check out Pedro’s across the street). The place was clean and well stocked with necessities. Beds were comfortable, pillows were good, curtains would have been nice due to the early sunrises.

We loved our stay! The space is beautiful and cozy. The walk to the family friendly beach was just the right distance for my 4yo. The neighborhood is adorable and friendly! With an amazing bakery and ice cream shop just around the corner! Dave was a great host and took great care of us.

Great place to stay, Ogunquit is such an endearing place to be 😄