Waterfront holiday rentals in South Portland

My husband, toddler and I stayed here and had a great time! We loved sitting on the roof deck and the living room has an amazing view of the water. We walked almost everywhere, which was so nice. Overall great location! Would recommend to anyone!

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.

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.

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.

Kate’s place is in a beautiful location and has so much to do. We loved the wildlife, the easy access to Portland and all the yard games. We can’t wait to come back!

Our group was two small families with kids ages 6 and 8. Everyone had a great time. If you’re looking for a home to get out into nature, this is it. The private dock and lake gave us hours of time to play outside. Kayaks, paddle boards, and fishing off the dock was fun and all part of the house. Kids had a blast and so did the adults. Perfect for family summer vacation. We had a few rainy days but either played board games inside or went into Portland which is only 20-30 minutes away. Visited Mackworth Island in Casco Bay. Must do if you want to have a day excursion. The house well kept and easy to navigate. We spent more time outside on the lake than inside.

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!!

My friends and I loved staying at Carol’s! Check in was so easy, and the location is quiet & close to the East Promenade. Amenities were perfect for what we needed, and Carol was so kind and friendly!

Just as described! Peaceful and private location with a responsive host!

Yvonne needs to get an INFINITE number of stars, not just 5. Her Luxurious property really stands out from the crowd and this is coming from a very picky guest with high expectations and love for cleanliness, beauty and comfort. Truly a home away from home. If you reserve this property to stay for an endless number of days, you will NOT regret it. This property offers you all: The one million dollar view, the beauty of nature and lots of things to do while feeling relaxed. We traveled with 2 kids, a grandma, and a small dog and we all enjoyed our time there. Yvonne has thought of every little detail and I doubt that many hosts out there would go out of their way to make their guests feel special. There was a welcome gift, lots of games were provided for entertainment, kayaks, paddle boards, fire pit wood, outdoor kitchen and bathroom.... The lake is beautiful and clean. You will NOT run out of things to do inside this big home on a very hot or rainy day. We will be coming back!

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)

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.

Julie was very responsive and so helpful with everything from check in to departure. The location was perfect so close to the beach and everything downtown. We love that she had a snack basket when we arrived. We had a nice stay.

Location was great; close to town, but quiet in the evening. Close to the beach. Tammie’s place was spotless! Coffee was delicious! Felt so comfortable and right at home. Excellent! If we ever would be back in the area, would not hesitate to stay there again.

All of Maine feels 'rustic' to me. This was a great Airbnb with that in mind and fantastic value for the area. It's a very short walk to the beach and right next to a great BBQ restaurant which serves local beer and even gluten-free pizzas! The roof deck was glorious. The TV is 'megalithic'. I cannot believe the bath isn't mentioned in the listing! It's deep. I brought bath salts and enjoyed many hours in the tub. Perfect! This was truly a home away from home with everything I could possibly need. Some of the windows don't quite seal so there is road noise in the bedrooms. It feels like the ground underneath the building has shifted over the decades so I'm sure straight lines for windows are impossible to sustain. It's a quiet road at night. One bed is firm, the other is soft. The hosts are very responsive.