Waterfront holiday rentals in Portland

The apartment is beautifully designed, spacious, relaxing, and comfortable. What more could you ask for? We enjoyed our 3-night stay. Read some of the assembled books on birds and enjoyed delicious food at the local restaurants. Alice was a gracious and responsive host. You will truly love staying in her apartment!

Jean is a cordial, friendly on site owner manager who takes great pride in her accommodations. No detail is too small to get her attention. Our unit was crisp, clean and delightfully appointed. We could not have been more pleased with our stay and delightful accommodations.

We would give this Air B&B even higher ratings if possible. It is one of the cleanest, prettiest and most comfortable one we have stayed at in our years of renting. The bed is amazing and we slept so well each night. It is now listed in our favorites and we look forward to returning.

In short, a unique experience where we met a few extremely friendly people. The property has amazing views of the harbor without noisy working boats. We would out this at the top of our rental experiences.

Jennifer's place is so interesting, clean and tastefully decorated! We enjoyed our stay very much and definitely would return there, as many guests do. Be sure to check out the wonderful nearby Salt Water Cod Cafe and the many Maine-made things from Seaside Creations on the road to the Giant Steps on Bailey's Island. Also, the chocolate from Jennifer's candy store up the road is really good. Thank you Jennifer for making this experience possible!

Adorable, idyllic, comfortable, serene. Couldn’t have asked for a better spot for our Maine Minimoon! Some places have 5 stars and aren’t really legit — this is not one such place. Hillary’s place fully deserves ⭐️⭐️⭐️⭐️⭐️. We look forward to staying again soon!!

Great place. Three separate bedrooms with new beds - we all slept great. Lots of very thoughtful extras!

Kevin’s place was exactly what we needed for our two family trip to Portland! We had just enough space for the six of us and we could walk to nearby places to eat, shop and more. Easy to drive a little further out for more attractions! Everything was as described and we appreciated knowing ahead what to expect. Kevin was quick to respond to any questions we had and I’m confident he would have been responsive to any difficulties if we’d had them! We would definitely come back and recommend this place to anyone looking for a spot downtown.

Easy 5 stars! Phillip was kind, proactive and responsive. The space, while quaint and simple, was clean, had all the essentials and, it was perfect for a week visiting my grandparents/ working remote! Not to mention my dogs loved being a half mile from the Bath dog park. Highly recommend if you’re looking for a Maine mid-coast getaway!

Amazing surroundings and views. The reserve loop walk is great.The perfect Maine coastal experience.

We booked the Beach Bliss House in OOB for our girls' weekend. There was more than enough room for the 8 of us to stay comfortably, and we especially loved the large kitchen/dining area. The dining table can easily seat 8-10 and it was put to good use for our meals and card games. Although we could only enjoy it for a couple of hours due to the weather, the roof top deck is amazing. The ocean view, ample seating, and hot tub are so inviting. At only 3/4 mile to the pier, you can easily walk to all the action in the center, and head back to the more peaceful location of the home when you're ready to relax. The beach is just steps away! This would be an ideal place to stay for a summer vacation. The host, Jason, was VERY responsive to any questions we had, replying to messages almost immediately. We would definitely consider staying here again and recommend to everyone.

Shirin’s home was the most beautiful and relaxing location I’ve ever stayed in. The view, the sounds of the birds, the space- I couldn’t have asked for more on our hopefully annual Maine vacation. Boothbay Harbor has captured our hearts, and I cannot recommend staying here enough. Close enough to drive 6 minutes to Coastal Maine Boatnic Gardens and just a few minutes to downtown- parking has always been relatively easy (and free) on the street downtown. BOOK TODAY!

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

I wanted a peaceful place by the water to unwind and Maggie’s home nailed it. Every aspect of our stay exceeded expectations. The deck views were amazing—islands, ospreys hunting, and a duck and her ducklings feeding along the shoreline. At low tide we poked around in the sand at the bottom of the rocks, and could have easily walked out to the center of the bay but it was juuuust a bit chilly for us. Easy to drive, park and walk along beach on the Atlantic side and explore. We didn’t have time to kayak but hope to be back to give it a go. So much beauty and nature, but with all the amenities that make it easy to relax. Maggie was responsive, and she and her family obviously care very much for the property. Check the propane BEFORE you plan to grill :), and bring flip flops to easily get from the house to the grotto (which was so comfy and cozy) and back again.

My family of 6 throughly enjoyed our stay. We loved the town of Freeport and Portland was just a short drive away. The house was incredible and the location was just private enough but still walkable into town if you’d like. James was wonderful to communicate with and we had no issues our entire week long stay. Would highly recommend if you considering this area.

Absolutely incredible! Gorgeous views, great neighbors and so peaceful. Loved having access to the bikes for daily rides. This is not a sterile empty Airbnb, this is a lived in and loved absolutely beautiful home. The layout is fantastic with nice touches throughout. The kitchen was not only beautiful but had great knives and cast iron cookware. I felt at home the moment I stepped inside. I definitely did not want to leave. Shannon was very responsive and welcoming. Highly recommend!

Great vacation place; I would definitely stay there again. Steps from the beach as listed; beach chairs available as listed. It was super clean, bright, and comfortable. There were 5 of us and there was ample space for each of us. Full kitchen. Attention to the little extra details with big impact--like: the extra USB & C tech plugs in EACH ROOM; cinnamon in the cupboard; enough towels, plates, forks; soap; backpack style beach chairs, & more. We could focus on relaxing and fun. Thank you for a great stay, Karen!

Unit was very clean, situated in a quiet residential area and within walking distance to many of Portland's best bars, restaurants and attractions. Host was communicative and provided clear guidance on check-in/-out procedures and offered up suggestions to local attractions. On my recommended list - dinner at Twelve (one of the best restaurants in the US, IMHO); on-site food truck tacos washed down with a Hazy IPA at Bellflower or Austin Street Brewery; an everything bagel with lox & morning latte at Forage; the East Promenade for a food truck lunch, then a stroll along the waterfront trail to the port area for an ice cream cone at Gorgeous gelato; afternoon coffee at Double Great Coffee; and a post-dinner whiskey @ Independence Ice. Only downside on my visit was the upstairs neighbor. Dude clearly isn't a principal dancer in the Portland Ballet, as light on his feet wouldn't describe him. Not a stereo or TV issue - you can just hear the noise from him walking (8AM-10PM when there)

This was a perfect location for enjoying being in the heart of Old Orchard Beach. You get live music down stairs, a few steps away from the beach, quick walk to downtown/pier. Totally worth it! The condo is beautiful and comfortable.

The place was very easy to find, great location. Walking distance along the beach and sidewalk to attractions, great access to the beach. Very clean and well maintained place. The hosts are very responsive and polite with good recommendations of places to eat and things to do. Would definitely stay again!

Great 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

We had a great stay at Julie's condo. Condo was clean and well furnished. Very close to beach. Easy to check in and get our keys.

My stay here was wonderful! The perfect homebase for our trip. Everything was exactly as described and then some. A great sea breeze and a cozy space to rest and relax before hitting the beach or walking into town. I felt right at home. I can't wait to go back again! 💜