Holiday rentals with a fireplace in South Portland

We loved this place! We were renting for our daughter’s college graduation, and even though it poured all weekend- we really enjoyed just hanging out at the house. Mostly I loved loved the king size bed and I’m going to ask where the owner got it - slept like a baby!

This was our second year staying at Don’s and it was great as always! Beautiful space, clean, updated, and well stocked kitchen/linens. Location to the beach can’t be beat and all the beach things you’d need are available for use. Don and Sue are both wonderful and we look forward to future stays.

I had a wonderful stay at Cutter House! The beautiful grounds, with the charming red barn and friendly animals, created such a peaceful and inviting atmosphere. One of the highlights was the visits from the friendly, snuggly Great Pyrenees dog—such a gentle and affectionate companion who made the experience even more special. I loved spending time outdoors exploring the yard. The home itself is warm, cozy, and thoughtfully appointed. With two bedrooms and two full bathrooms, it was comfortable and convenient. The kitchen was well-stocked, and the fresh local coffee beans made my mornings extra special. The host Maria, was welcoming and communicative, providing helpful local tips and making sure I had everything I needed. Cutter House is the perfect retreat for anyone looking to relax in a beautiful, cozy setting with a touch of furry warmth. I look forward to returning! Don't forget to ask about Grace! She holds a record in Maine!!

This place was super clean with incredible views. Highly recommend.

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!

Great location and fully stocked with everything we needed - even down to beach toys for my kids and a wagon to haul it all back and forth!!

Such a great little spot in one of the nicest corners of Peaks Island! John was great, being flexible with me when my arrival time needed to be changed up. Would visit again and again!

This place is absolutely wonderful. Peaceful and beautiful. I wish we could have stayed longer. Our doggies loved the backyard. Thank you!

Who knew that inside an assuming building is a massive, quirky and cute space? It’s also in the perfect location close to restaurants. The apartment has everything you need and the space to host friends or family. The host was responsive. As someone who has lived in Portland and in many historic homes, it’s very normal for even the best renovated places to have a couple of more rustic details (wear & tear). The previous review disgracing this place is by someone who clearly this was not a match (they should have stayed in a modern hotel). It’s obvious that the host has been incrementally restoring this place and putting their own sweat in to make it a great airbnb. I would definitely stay here again. No question.

We had a car so this location was fine but might be a little far if you were planning on walking during your trip! With car it was perfect! 10 minutes to most places we wanted to go, a quiet street, cute place!! We would stay here again!

David and Valle’s house is welcoming, and it was just right for our family get-together. The kitchen is very well set up for cooking, and the counter is both beautiful and a great place for gathering and conversation. There are many lovely touches in the house. We appreciated the yard and gardens, and our dog loved the walking trail. The location is peaceful but just a few minutes from Portland. David communicated well and offered helpful ideas for our visit.

Caitlin and her adorable space were amazing! My friend/assistant trainer and I stayed two nights for the weekend to go to a continuing education dog training conference in Ossipee, only 25 minutes away. The host does not typically allow dogs; however, they were ADA compliant and had no issue allowing my friend/assistant’s well-trained service dog. Other accommodations in the area did give us a hard time, so we chose this space for many reasons, including the host’s welcoming attitude.

We slept like babies for two nights. The room was very dark and the bed was so comfortable. The shower was awesome and it was spacious and comfortable. We were hoping for the beautiful views but Mother Nature had other plans - rain and fog. Their property is stunning. Sue and Arthur were great hosts. We’ll be back.

Loved our stay! The airbnb is located above a restaurant, so parking in the assigned spaces can be a bit tricky if you arrive at night, but still no issues as we parked in a restaurant spot until we could move the cars later. The location is great, walkable to town and the cliff walk. The inside was more spacious than we anticipated from the photos and it was so nicely decorated! Would definitely come back! The side door was a bit tricky to lock, so I’d recommend only opening if you plan to use the little porch area with the full wall opened up.

We loved staying at Stacey’s place in South Portland. The apartment is beautiful, stylish, and cozy. Stacey has everything you could ever need and more. The location is great— in a quiet neighborhood in very close proximity to downtown Portland. We loved walking along the nature path just steps from the apartment. Stacey was very quick in responding to our questions. Overall, this may have been the best Airbnb I’ve ever stayed in. We would definitely book with Stacey again.

Wendy’s place was really nice and the hot tub is very private.. we definitely got our usage out of it… Wendy herself was extremely kind and open minded. She didn’t rush us out come check out, instead, she encouraged us to stay a little longer and enjoy the hot tub before our long journey back home.. she gave us good tips about golden gems only locals know about 🥰 She did have a cool book to share reviews but I didn’t have a pen.. also we left grape soda in the fridge from Canada for the next person to try!! Thanks again Wendy 5⭐️

My husband and I stayed here for our baby moon and it was perfect! The location couldn’t have been better and the airbnb was stocked with everything we needed. Nick was super responsive and made sure our stay was wonderful. We will absolutely be back!!!

Matt’s place was welcoming comfortable beds, well equipped kitchen. Matt was always responsive within a few minutes. Matt’s place was conveniently located to Portland with restaurants and shops. Spent A day at Cape Elizabeth, Peaks island and dinner in Naple….. previous visit was to Boothbay Botanical garden Really a great state to visit!!!