Pet-friendly holiday rentals in Portland

Our son, his girlfriend, my husband and I enjoyed staying at the cottage in late October 2024. The location was quite scenic as it overlooked Casco Bay, near Portland, ME. The host made suggestions that we followed (bringing firewood & blankets). The kitchen was equipped with utensils & coffeemakers. The neighborhood was quiet. We enjoyed walking in the local preserve along the water and took advantage of visiting the Portland Museum of Art and eating at The Honey Paw, an Asian fusion restaurant.

Great place to stay and great people to work with! We had a wonderful stay.

This is the 2nd time I've stayed at Emma's place. I came both times for a workshop and ceremony that took place in both Freeport and in Portland. Drives to Portland were the longest, and not too taking, and I chose to stay at Emma's place BECAUSE of the way the house holds me: the spaciousness, the attention to art and wisdom, the lighting and unfussy-yet-design-inspired furniture choices, the plant life, the textures and colors: all these things are soothing and welcoming. It was a pleasure to drive "home" exhausted, knowing what it feels like to open that back door.

Can’t say enough about how great our stay was! Andrew was incredibly responsive, let us check in early and check out late without even asking. It was a great location on the island, very walkable, even for my mother with a bad knee (she was exhausted after the first day though). Would absolutely stay again!! 10/10

Perfect weekend retreat for a small family with a young one. Close to downtown, museum, and the firepit was so nice at night. 5 stars all around and will return in the future. Thanks Phillip!

Jeffrey’s guest house is super special, it was amazing to be able to look out every window to experience coastal Maine and so serene and peaceful. Located on a beautiful property right on the bay in a wooded setting. Very private and quiet. We absolutely loved our stay - in fact we extended it another 3 days to be able to enjoy it longer. Jeffrey was very accommodating and even credited us for the 2nd cleaning fee charged by Airbnb because we needed to change our payment method for the extended stay. I can’t say enough about the comfy bed!! I felt like I was sleeping in a cloud with super soft sheets and perfect mattress. I wish all Airbnb hosts were as thoughtful about the personal touches as Jeffrey. I had to work a bit during the trip and the internet was very stable and easy to connect to. It was a perfect retreat for us. Highly recommend staying here! We will. Definitely will Return!

Nancy’s home is absolutely a magical way of visiting Portland! It’s spacious, beautifully decorated, cozy, AND close to everything by foot. Highly recommended place to book!

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!

I would absolutely stay here again! The check-in process was smooth, and Michael was incredibly flexible and responsive to any questions we had. The directions to the property were clear and easy to follow. Although we didn't cook while we were there, the place had everthing you would need to host. The house comfortably accommodated all six of us for the night, and since the weather was beautiful, we spent much of our time enjoying the stunning backyard. The entire setup was absolutely perfect—couldn't have asked for a better stay!

We would 100% recommend Dina’s place to ANYONE (and we hope to be back)! The place is beautiful and would accommodate a small to large family. The pool and hot tub are incredibly nice and peaceful surrounded by trees. The furniture is incredibly comfortable and the kitchen great to use. Dina is also incredibly thoughtful and quick with her replies. We got a little turned around arriving at night (the GPS lead us up the road a bit), but we found it!

Gorgeous house, peaceful area, a great back deck with pool and hot tub! Jey was a great host, very helpful and quick response time. The house was very clean and put together. I would totally recommend staying at jeys house!!

this house was perfect for a girls weekend getaway!! spacious and beautiful, still super close to all the activities in portland, but wonderfully peaceful! it was too cold to use the pool but it looks great and I would love to book this house again later in there summer to be able to use it! the beds were super comfortable and easy off street parking. thanks for a great stay!

We had a wonderful stay in Angela’s beautiful home. It had great amenities, was super clean, and had everything we needed. Loved the pool and fire pit. The kitchen was roomy for cooking too. 5 stars!

We had a magical getaway for the weekend! We watched a porcupine forage around the yard both evenings from the hot tub. We named him “Steve”. We loved the walk down to the river and enjoying sunrise from the hot tub with coffee. We will definitely be back!

We had a wonderful stay. The house was spotless and beautiful with a fully stocked kitchen, super comfortable beds, and great amenities. Our kids loved the heated pool , hot tub, board games, and the easy walk to the beach. The location is also great and close to lots of restaurants and shopping. Stephanie was very kind, helpful, and quick to respond to any questions.

great accommodation, thoughtfully decorated, clean with everything you need. Perfect as a hiking base, lots of recommendations from the wonderful hosts

This was a great place to accommodate five or six people. The kitchen was well equipped with all the tools we needed to cook at home, including several spices. We enjoyed a lovely patio to sit on in the back. There were a few board games available that we enjoyed. This was a great option!

Off the grid enough to feel completely alone in the woods, but close enough to where you can get dinner or find other things to do with only a short drive. Highly recommend.

Wonderful stay, the place was in a beautiful location, walkable to Wolfe’s Neck Farm where we love to walk. My husband and I were there the first few days, then our adult daughter joined us for two nights. The place is small (described accurately) but the three of us found it very workable. The king bed was very comfortable. There was plenty of outside patio space to lounge and soak up the sun when it was out. This was a work trip for us as we were getting a property in a nearby town ready for sale. We didn’t have time to use the provided kayaks but hope to in a future stay. The hosts very friendly and accommodating, highly recommended this property.

This place is perfect getaway for a couple. Looks exactly like the pictures. The location is amazing. We will definitely be back.

The views were amazing and the place was perfect! They’ve thought of everything (beach chairs, extra linens, coffee) and the flowers and birds make the property even more lovely. I stayed with my daughter and there is privacy within the space. The beach is a five minute walk from the house. We will definitely stay again!

Sadie’s place was a great central location to parks, the waterfront, restaurants, and more! Once we got to the Airbnb, we parked and didn’t use our car for our visit. The house is 1 min from a nice lookout spot of the city at Fort Sumner park. Bed was comfortable and kitchen was well stocked for those who want to cook. Highly recommend!

An absolute gem of a place in the perfect location. You can walk anywhere from it, it’s in the action but also quiet at the same time. Was the perfect place for the perfect trip. Heidi was so nice and helpful!

We recently stayed at this Airbnb and had an incredible experience from start to finish. This place truly exceeded my expectations, and I wouldn’t hesitate to recommend it to anyone. First and foremost, the location of this apartment is unbeatable. It’s situated right in the heart of Portland, making it incredibly easy to walk to everything — fantastic restaurants, great shopping spots, and close to the waterfront. The apartment itself was spotless