House holiday rentals in South Portland

Great backyard with a pool, hot tub, fire pit and privacy with the woods.

Jason was a fantastic host—responsive, helpful, and easy to communicate with. Although we encountered a few minor issues during our stay, he responded immediately and went above and beyond to ensure everything was resolved quickly. The space itself was absolutely beautiful and made for a wonderful stay. I would highly recommend this place to anyone and hope to return in the future!

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!!

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!

Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!

Beautiful home in a quiet, family-friendly community. We loved being able to walk up to the pool and play in the game room in the main clubhouse area. The house is a short drive to downtown Kennebunkport and local beaches. It is a quick 30 minute drive up to Portland. Our daughter loved sleeping in the private bedroom upstairs. The kitchen was fully stocked with appliances. The space was immaculate when we arrived. Steve was responsive to any needs we had during our stay. A great find!

Great place to stay! Clean and comfortable. Excellent location, close to many restaurants, and other activities!

Central location, but was surprisingly very quiet and private. Kelsey is an excellent communicator and host.

Kevin's place worked really well for my two dogs and myself. There is a fenced in back yard. I liked the setup of the primary bedroom with the attached full bath and laundry. Comfortable bed! Very quiet neighborhood and very convenient to access other areas of Portland. I really appreciated the back deck setup. I need to find the comfy chair they have out back for my own home! Clean and usable kitchen. Nice stack of Maine materials and recommendations for local items to check out. Overall, a very pleasant stay, thank you!

Omg. SUCH a gem!💎 The house - adorable!✅ The host - amazing, communicative, friendly and SO sweet!✅ Incredibly dog-friendly✅ Safe, very quiet neighborhood✅ This was such an incredible stay! The house, the yard, the twinkle lights, the beach, just everything! I was here on a work trip in the winter and I’m crossing my fingers work will bring me back to SoPo in the summer when all the flowers are open and the water is warm! Even in the winter, it’s a beautiful, magical space 💕 couldn’t have asked for anything more! Lisa, thank you thank you for sharing your incredible space with me & Sookie. It has SUCH a good vibe and you are awesome! 💛 (Omg and the beds?! SO comfy!!)

Great place! Beautiful neighborhood to walk in and comfortable, quiet place to come back to. Finn was very helpful and we enjoyed our stay.

Beautiful spot for a quick getaway or longer vacation. Host was very responsive and sent clear instructions for check in and check out. Sent great recommendations for places close to the condo. Would definitely stay here again!

Angela‘s place was very clean had a lot of cute little things around that made me laugh. We flew in very late at night when everything was closed and we’re thankful to see that she had water in the fridge and coffee for the morning since nothing was open for us to stop. Very close to downtown Portland.

Here’s anCarley's home was wonderfully equipped with all the essential amenities to make my stay comfortable. I particularly appreciated the thoughtful touches like coffee (with filters!) and a well-stocked kitchen, which made the space feel warm and homey rather than like a typical hotel. During my visit, it snowed, and Carley had everything I needed to stay safe, including a shovel and rock salt to keep the steps clear. The extra blankets were a cozy bonus that I truly appreciated on chilly nights. The home is situated in a quiet, charming neighborhood with convenient access to nearby stores, making it an ideal home base for visiting family in the area. Highly recommend!

Suzanne & Brian’s place was absolutely perfect for a girls weekend away! Beautiful home with all the amenities you could think of in a very serene setting. It’s very clear they love their place and take excellent care with it. Super responsive and friendly hosts- I wish every Airbnb experience was like this! Such a nice quiet getaway still within easy driving distance to Portland and plenty of things to do.

We really enjoyed Gregory's home! It was great for a big group - very spacious. It was also well located - close to various shops and restaurants and only a 20 min drive to Portland, but it felt very secluded and peaceful. The property was beautiful and there were some lovely walking/running trails in the immediate vicinity. The hot tub was also a very nice perk - would definitely stay here again!

We had a great stay! Everything was exactly as described and Ian was very responsive.

Beautiful home in the heart of old orchard!!! The space was peaceful and quiet! Super close to the beach while not too close to any noisy streets. The home itself is perfect for a little weekend getaway for two! Plenty of parking and easy to find even at night! Overall a great experience would definitely stay again!

We loved our stay in Portland. The house was beautiful and lay out was great. Our group enjoyed the spacious kitchen and open floor plan. The location to downtown Portland was awesome with just about a 10 minute drive to get to Old Town! Check in was a really easy process and the host was very attentive and thorough! 10/10 would recommend.

We really enjoyed our stay at this Air Bnb. We have stayed at over twenty different locations with Air Bnb and this was the cleanest. Beds were comfortable, space was open and uncluttered. It was nice to be able to have dinner on the back deck. We would definitely stay here again.

We had a great stay at Capt Gene's! He was very helpful before our trip with giving ferry instructions which made our first day less stressful and more enjoyable! I would definitely recommend anyone to stay at Capt Gene's!

This cozy yet spacious cottage by the sea was so well appointed and peaceful. We went with another couple and both of our rooms faced the sea so we all got to hear the waves when we retreated to our rooms at night. Lisa was easy to communicate with and very helpful! If we ever get back to Peaks Island….we would definitely stay here!! Thank you Lisa!

Beautiful, well-appointed home. All the little things add up to a stress-free experience. Fully stocked with towels, cooking supplies, even q-tips if you forget your own! By far the cleanest, most comfortable AirBNB I've stayed in. Photos don't do justice to the view from inside and from the patio. Incredibly quiet at night and the feeling of seclusion helped recharge my batteries. Super clear directions and entry instructions. Nothing beats dinner or wine by the firepit overlooking the bay except for the sunrise over the water. Would 100% stay again.