Family-friendly holiday rentals in South Boston Waterfront

This condo was perfect for what we needed. Just two bedrooms, a kitchen and living room, so we could relax in between walking adventures. I wish I had come across this back in the fall when my daughter was playing soccer for Northeastern because the soccer field is literally across the street. There is a nice walking trail about a quarter of a mile away. We really liked Coolidge Corners. Easy to get Ubers. The place was perfect and comfortable and easy to get in/out.

We had a great stay! This house was in a great location, and very nice/spacious. We also appreciated the very thorough and clear communication regarding check-in etc, before the stay. I highly recommend Joel as a host!

The apartment was exactly like described in an amazing location. I was attending a conference at the EXPO center, and it was an easy 25 minute walk there and back. Area is safe and clean. The best feature is the is less than a minute walk from a beautiful park and beach. Multiple Restaurants within walking distance and had no trouble getting items delivered. Would definitely stay again. Thank you so much Tanya!

Very quiet area. Close to the orange Line and multiple busses. Check In/out was easy. Apt room temp was good. Hot water was extra hot, so also a plus. Cable TV was nice.

Great place. We loved the location and the surroundings. Wally was you receptive and proactive. Everything we needed was available. The instructions and local information was great and even though we had a plan of things to do, it provided us a couple of awesome ideas for our down time. Would definitely stay there again and would recommend. Thanks Wally.

This is such an amazing place. We arrived very late but the instructions to get in were great and there was stuff in the fridge to keep us going until the morning. Maude had left detailed instructions and tips to work the lights etc. We felt really comfortable and probably the most relaxed on our US trip. It is also a very walkable and safe area. Don't hesitate to stay here!

We had a fantastic stay at Louisa’s beautiful place! The home was spotless, filled with great natural light, and equipped with everything we needed for a comfortable stay. The location was perfect—just a short walk to Harvard, making it incredibly convenient. Our time here was not only enjoyable but also highly productive, thanks to the peaceful atmosphere and charming surroundings of this lovely street. We will definitely be returning to Louisa’s amazing home, where we truly felt like we had a home away from home. A special thanks to Louisa and James for their hospitality and for making this trip so wonderful and unforgettable.

Had a wonderful stay with my friends in Boston. The rooms and living spaces were very comfortable and clean. Michelle was very reachable and responded quickly. Would recommend this home to anyone.

Our stay in Lionsgate cabin in Cohasset was heavenly abode for a week during our stay in the last week of May. The cabin is located in peaceful surroundings with beautiful bird watching areas. The bird feeder outside our cabin kept me and my toddler daughter occupied throughout our stay here. The lawn areas and seating outside are great areas to take a stroll and listen to nature’s music. The cabin is comfortable and cozy with enough provided even for a long stay. It is located within short travel distance from many good restaurants, grocery shops and metro. Very close to the beach, we visited Nantasket and Hull many times during our stay. We loved our stay here and will stay here again. Highly recommend this cabin.

We very much enjoyed our stay at Kevin’s place. Great location. Easy access to the train and the city. Lots of nearby restaurants. Kevin was friendly and accommodating and provided some nice treats to eat and drink. The apartment was very comfortable. We especially enjoyed sitting out on the rooftop patio. We will be sure to stay again when visiting the area.

The place was perfect for our stay. The commute to Cambridge went smoothly and we were close to many attractions in Boston. It was nice to come back to in the evenings after long days, very comfortable.

We had a fantastic stay at Laurie's place. We loved the extras in the kitchen like half & half and coffee! We had enough towels for our stay. The beds were comfy. Laurie was very responsive to the questions I had. I would recommend this place for sure!!

Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!

The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.

The host communicated well and was very thoughtful. The bed wasn't very comfortable and the heating unit was a bit tricky to figure out, but overall, we had a great stay.

We had a wonderful stay! It's very close to Boston, and other area attractions like Salem and beaches, but still peaceful. We enjoyed sitting at the pool. Kathy was very responsive and checked in with us to make sure we had everything we needed. They provided clear instructions for getting into the space and I had no issues navigating in and out of the neighborhood or to the basement apartment. I would definitely stay again if I'm needing a place in the area!

We needed a nice little place to stay while we visited family and friends. This was perfect. Cute and convenient, plus lots of fun amenities like a clubhouse, ball courts, kayaks and the lake. We went off season, so the pool was closed and it was too cold to boat, but it was still fun. We enjoyed walking the community, playing ping-pong and driving the golf cart.

Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.

Our second time, weeklong stay! And we hope to do it again next year. Just simply meets our needs very well. It's a joy to stay here!