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!

a wonderful place to stay.

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!

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 house was perfect for me and my guests! All 7 of us fit perfectly, It didn’t feel too overcrowded! We loved the beautiful view off the deck and the hot tub was an amazing touch! The house was very clean and had everything we could’ve needed. I loved how clear the instructions were for everything and how responsive the hosts are if you need anything!

Everything was as described! Very tranquil setting. Loved sitting on both the sunporch and deck watching the boats go by. The house was immaculate and very well equipped. NIce to relax without the distraction of tv for a change. Enjoyed their Bose radio.. Also the verizon phone /computer connection was excellent. It was a great home base for exploring the mid coast of Maine. Lots of good restaurants near by and the owner offered many heloful hints as to what to see, where to est and what to do. His communication was excellent. Would highly recommend this rental.

David could be the greatest Airbnb host we’ve ever had! He was extremely attentive and answered all my questions before, during, and after the stay. We had a welcome packet of snacks, drinks, and small gifts for the kids waiting for us when we arrived. The skee ball machine was actually even more fun than we thought it would be and we used all the various games included in the house for a memorable “family Olympics”. The neighbors were quiet and it was easy to get to some great destinations like Portland and Kennebunkport. David’s house was a lot of fun!

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.

Our stay was awesome! It was very clean and very accommodating! Tim was also super responsive, and quick to get on the phone with us when we had questions about anything we needed! Would definitely 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.

Oh gosh where should I start? This must have been one of the most beautiful Airbnbs I have ever stayed in. It felt so comfortable right from the start, there were fresh flowers on the table and the bed is extremely comfortable (and a King size bed which is a huge plus). The kitchen is well equipped, the bathroom is spacious, the living area is super cozy and there are two seating options for eating your meals. Our favorite one was the round table right by the beautiful big window. There is a huge tree outside and the surroundings are so green and lush it was amazing! Parking is right outside, the place is very easy to find and it‘s super quiet at night. Oh and the black out curtains, perfect! Stacey has amenities laid out if you ever forget or run out of anything. All in all a perfect place, 5 stars! Thank you for putting so much love into this place, Stacey, it really shows!

Nice stay, nice host, lots of recommendations in binder for things to do. Nice hot tub. Cozy place and location. DQ right across the street.

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!!!