Holiday rentals with outdoor seating in Casco Bay

Stayed at Bethany's place for a long weekend at the end of the season. The location is unbeatable, the house is situated on its own little peninsula in a stunning cove; it feels very private and has amazing views of the water. There's tons of outdoor space and seating, along with several kayaks. The house itself is clean, quiet, and peaceful, although it's definitely small--probably best for one or two people, or a couple with a small child. Access is down an unpaved road but Bethany's very clear instructions made it easy to find, and she was responsive to any questions we had. Harpswell abounds with areas to hike and explore, lots of good places to eat (though you will definitely need a car) and is less than an hour from Portland and only half an hour from Freeport.

We had a wonderful stay at this beautiful beachfront home with our extended family, including a total of 6 adults and 5 kids. We had two additional adults spend one night, there was plenty of room for everyone. The house was spacious, comfortable, and perfectly suited for a group of our size. The location is unbeatable, right on Drakes Island Beach, with incredible views and direct access to the sand. While we didn’t go in the water, we spent plenty of time relaxing on the beach, walking along the shore, and enjoying the peaceful setting. The home was clean, well-maintained, and stocked with everything we needed. The large deck and open living spaces gave us plenty of room to spend time together and unwind. This was a perfect spot for a relaxing family getaway, and we’d absolutely return again. Highly recommended!

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!

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!

If you’re looking for a place in Freeport, look no further! I cannot say enough nice things about this experience. 1. The location is literally just minutes from the outlets, restaurants, etc…BUT away from the main road so you feel a neighborhood vibe vs the down town vibe which is SO relaxing. 2. The home was immaculate. Sheets, dishes, floors, bathrooms…you name it, it was clean! We felt so comfortable letting our children play and be kids. 3. The hosts were incredibly responsive, even in the middle of the night! You can just tell they’re good people◡̈ 4. Everything was thought of, from baby shampoo, to paper towels, trash bags, kids books, even ice in the ice trays! Everything we didn’t know we needed was provided. 5. The furniture was super comfortable. Every person that stayed said their bed was amazing, even the couches felt like you could just melt into. I could keep going, but bottom line, this whole experience was 10 stars and I’d book again in a heartbeat. ♡︎

A very nice, clean and convient apartment (house) near active area of Brunswick. Peter was quick to welcome us in person after we checked in. The house was well-appinted, relatively quiet and had all the amenities we could ask for. My only (small) negative might be about the mattress. I found it very firm, like a futon. Some may find this therapeutic, but I found it difficult to sleep well on. It's only a small issue; he cannot cater to all guests' sleep habits. The location is right on a busy thoroughfare and there is a lot of traffic during the day, but at night things got pretty quiet. The house is well insulated and very little road noise is heard. Overall, this is one of the best properties in which we have stayed over the years with Air BnB. I'd return. It's a very nice place, convenient location and good value. Enjoy!

John was responsive and flexible. The area was quiet, an easy walk to the water and close to some nice restaurants. Also, an easy and quick ride to downtown. His place was clean and comfortable. Great place to stay if you are visiting Portland.

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

I had a lovely stay. The accommodations were elegant and comfy, and Dan's hospitality was warm and responsive. The location was perfect for dining, the art museum, and access to the waterfront. There were some special touches that made it feel all the more welcoming (I won't spoil the surprise for future guests). It is a place I hope to return to in the future. Many thanks to our hosts!

Great location that is nearby for runs/walks and quick driving commutes to downtown and other hot spots. The space was cozy and clean.

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.

This is the perfect stay for two people for a getaway in Portland! You'll get a quiet spot in a nice neighborhood that is walkable to anything you would want to do or see in town. Sharon and Eric were awesome hosts and their place was a great place to recharge each day after being out and about in Portland. Highly recommend you book here!

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!

I really enjoyed my stay, and appreciate the proactive communication, lovely and comfortable apartment, and how walkable the area is. I wish I could have stayed longer because Nicholas and Emily have so many great recommendations for what to do in the area!

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.

This cute little cottage was perfect for my stay in Old Orchard Beach. My stay was in cold January but the cottage was warm and cozy. The highlight was being steps from the beach and being able to roll out of bed and catch the sunrise each morning.

This was a teeny tiny condo (<200 sq ft!) but spotlessly clean, well appropriated, and a great location. The bed was comfy and the loft area was tall enough to sit up and move around. It was a 5 minute walk to Pine Point Beach. There are about dozen other tiny cottages in the condo association, clustered around a central parking lot, so if all of them were full there wouldn’t be a ton of privacy but we were there in the off season and it was peaceful and quiet.

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.

Amazing apartment at a great location! Lots of character and the newly renovated kitchen was a plus. Very quiet neighborhood that allowed us to relax. Dave is a great host and was very helpful and flexible when it came to our check in time. We definitely recommend his place and will be back soon! Thank you Dave!