House holiday rentals in South Boston

My family and I were fortunate enough to spend the thanksgiving holiday here. It was the perfect space for a group gathering. Would highly recommend!

Great option when staying in Newton and right down the street from an incredible entrance to a hiking trail. Serge was a great host and kept us informed the entire trip.

Amy was very responsive and communicative. The house was clean and maps took us right to the home. It was too early in the season to enjoy the pool but it was pristine and would have been great for hot summer weather. Amy was wonderful with trying to accomodate any requests and we liked the location from easy access to Salem and within a one hour drive to Boston!

I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽

Super fun and eclectic house! What really made the stay were the owners, they are thoughtful and very responsive, they clearly care a lot about their guests!

Scott was very easy to communicate with, and he was very nice. They were so thoughtful and even left us a dozen eggs from their backyard chickens! The place was spacious and peaceful. Check in and checkout process was very easy!

Absolutely incredible stay. The host was very helpful. The house is absolutely beautiful, and the lake is stunning. The basement was so so fun- darts, ping pong, billiards, and more games. We miss the house already!

Hands down one of the best Airbnbs my family and I have stayed in! We didn't want to leave this place. To top it off, Michelle is a great host. 5/5 rating for sure!

We had a fantastic stay at Johnny’s place. The house is great - comfortably enough space for a family of 4 and well configured, well-located 5 mins walk from great coffee shops and restaurants in Charlestown and only 20 mins walk from the North End and central Boston. Johnny was extremely accommodating. Highly recommend!

We can’t rave enough about how wonderful of a host Steve was! My friends and I visited Boston for the first time for my birthday and Steve not only was incredibly responsive and made sure we were well taken care of the entire trip, but he also got a surprise Birthday cake to celebrate our special occasion. Steve was also very generous to let us stay longer in the Airbnb when our flight got delayed. He also had a great list of nearby restaurant recommendations and things to do. The Airbnb was fantastic and so clean and in a great location. The beds are comfy, utilities in great shape, and the living room and patio was such a perfect space to hangout. We all agreed that this was hands down the best Airbnb experience that we’ve ever had. Hats off to you Steve. We will definitely be back again for another amazing stay! Such a wonderful, stress free stay.

Everyone had such a great time. The house was in a great location and was big enough for our family gathering. The host was wonderful and very responsive. The house was very clean and had all the amenities that we needed. I would definitely rebook the next time we are in the Boston area.

Beautiful home, allows for a stay in Boston without the hustle and crowd of Back Bay. Easy walk for breakfast or lunch, quick drive into town for dinner or activities.

Susan’s home was perfect for my family’s visit to Cambridge. Very comfortable in a lovely neighborhood, easy walk to Harvard Square. Susan was easy to communicate with and very responsive - she even left us some great neighborhood recommendations. Will definitely stay again on a future visit!

We had a great stay! The house was very clean and in a quiet neighborhood. It was easy to find and made a perfect central spot for visiting Boston and exploring the coast. Javer was super responsive and communicated clearly throughout—would definitely stay again!

We really enjoyed staying in your beautiful home. It was decorated so nicely and so well appointed. The bathroom was so clean and bright. The neighborhood is so pretty and we enjoyed taking a walk with the dog when we arrived. The beds were comfortable. We would definitely stay there again.

It was a very pleasant stay at your house - it was very clean and very safe. Our parents had the most wonderful time staying there. Irvin was very responsive and always available during the entirety of our stay.

Errington is an extremely responsive host and our group enjoyed our stay! If we come back to Boston we will rebook.

Had a lovely stay at the apartment. It is spacious and is in a convenient location about 10 min walk to subway and could easily use public transport to get to points of interest in 15-30 min. Close to several parks/greenspaces and good restaurants. Maria is a very helpful, considerate, and polite host.

Great location!!! We were in town for a graduation, the location is super close to the train station and there are restaurants around the area. The house is conveniently located and is spacious. It was large enough to accommodate our entire party of 7. The rooms are spread between the first and basement floors. It was a great stay, we loved Boston! I would recommend and stay again.

Beautiful house in a beautiful neighborhood. We loved staying here!

This is my third booking at Kay's place. That should say enough when there are many other choices.

Carmen was a wonderful host! The location is perfect to walk everywhere to get a bite to eat or get needed items. Ferry not far away if you want to take it back and forth to Boston. The place was very clean, beds were extremely comfortable, and we had everything we needed.

We had a fantastic stay at Sue’s place! She was incredibly responsive and attentive, clearly committed to making sure we had the best experience possible. The home itself is perfect—clean, comfortable, and thoughtfully set up—and the location couldn’t be better. Honestly, there’s nothing we’d change. We had a great time and would absolutely return. Highly recommend!

What a spacious & great place to stay on the 1st floor of the house. Open kitchen & living room with a comfy couch. A kind gesture of nice snacks & drinks. Clean, bright & smelled like fresh laundry. Spacious bedrooms 2 full bathrooms. When we arrived it was warm in the house but the window air conditioners do the trick of cooling it down fast. Close to everything you need by driving or a quick Uber ride. Plenty of street parking & parking in the driveway but the driveway is narrow so a bit difficult for a bigger vehicle. Comfy beds, fridge & freezer. Plenty of dishes if you need them. Would definitely book again. Very responsive, host.