Waterfront holiday rentals in South 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!

My stay here was fantastic! You truly cannot beat this location. It's perfectly situated with easy walking access to local shops, restaurants, and scenic spots. Parking is right outside, so exploring other nearby towns is a breeze, too. The place was clean, cozy, and had everything I needed for a comfortable stay. Highly recommend!

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.

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.

These accommodations were perfect! Overlooking the Casco Bay harbor, the view was even better than depicted in the pictures. The condo was meticulously clean and very well appointed. The beds and pillows were so comfortable we slept even better than we do at home. The location could NOT have been better! It overlooks Portland’s old-town shopping district, and is easily walkable to all of the best restaurants in town. There is a beautiful walking trail just up the street, and you can easily catch the ferry to the islands from this location. It is convenient, beautiful and welcoming.

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

I have been renting in this area for 40+ years. Mara's attention to detail was over the top. We arrived to a note and a gift card to the local lobster places. (Who does that!) There were bones and everything we needed for our sweet dog. The outside shower was the best and the only one I used. Having a 2nd bathroom in the basement and laundry was great. Air conditioners and a well stocked kitchen. And the sunset views and nights around the fire with family were the best. And use of the garage with bikes, sand toys and kyacks-never seen that before. Wish I had booked for a few more days. Will definitely come back next year. Thank you!!

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.

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!

This was our fourth stay at Ralda's house. It is easily one of my favorite places to stay. The house is pristine and comfortable, and the proximity to Higgins Beach can't be beat. We're already looking forward to our next stay!

This home was beyond expectations. The views are amazing. Going to sleep with the ocean breezes blowing in , listening to the waves and then waking up to the view of the water is just awesome. Immaculately clean, well stocked and great location. Although we would have been content just to sit and enjoy the views every day, there are great day trips. Besides the light house visits, hiking in the state parks, shopping in Freeport, browsing in Kennebunkport and even a day trip into Boston. We all (mom, dad and 2 grown sons) loved every moment of our 9 day stay.

Had a great stay here! We have 9 guys in town for the weekend and this was a perfect set up - plenty of inside and outside space, great kitchen and amenities, great seating and furnishings, fully stocked supplies and even some snacks, 5 minutes to downtown. Highly recommend this property for a large group or even a couple of families with kids for a getaway that is still accessible to downtown Portland and the area. Michael was super responsive and pleasant to work with. Will definitely be back if we end up in the area in the future!

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!

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 absolutely loved our stay at Greg’s place in Old Orchard Beach. It was easy to get in and Greg provided the codes to the doors as well as explained where to park. The condo was spacious and very clean, one of the cleanest Air BnBs I’ve stayed at. I typically clean on arrivals but didn’t need to this time. We had the sliders open the majority of our time and enjoyed looking at and hearing the ocean all the time. The one very warm day we had, the AC worked great. The bed was super comfortable, for once I didn’t long for my own bed at home as this one was almost as good. The location was great and it was easy to walk to everything. The music playing at the Brunswick was great entertainment at night. We enjoyed hanging out in the living room or on the balcony listening. It did go until late but it didn’t bother us. We would definitely stay at Greg’s condo again and plan to book our next trip soon. It’s been one of our favorite vacations we’ve had in a while.

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! 💜