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Family-friendly holiday rentals in South Boston

Find and book unique family-friendly homes on Airbnb

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Popular amenities for South Boston family-friendly rentals

Family-friendly home rentals with a hot tub

Flat in Fenway-Kenmore
4.73 out of 5 average rating, 83 reviews

Renovated 2Bed, 0.5 mile to Longwood Med Hospital

AmyRating, 5 stars1 month ago
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.
Guest favourite
Home in Brighton
4.96 out of 5 average rating, 266 reviews

Spacious 3 bed, in unit laundry, central Air

BillRating, 5 stars3 weeks ago
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!
Guest favourite
Flat in South Boston
4.91 out of 5 average rating, 66 reviews

South Boston. Minutes away from Convention Center

LeeRating, 5 stars2 weeks ago
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!
Superhost
Flat in Roxbury
4.78 out of 5 average rating, 329 reviews

Modern, Spacious 1BR for 4 - Easy Marathon Access!

YsamarRating, 5 stars2 weeks ago
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.

Family- and pet-friendly home rentals

Guest favourite
Townhouse in Everett
4.91 out of 5 average rating, 253 reviews

#9 Modern Home 15 min to Boston. Relax in Style!

DawnRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars3 months ago
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.
Guest favourite
Flat in South End
4.96 out of 5 average rating, 381 reviews

Charming South End Duplex (Pets Ok)

StephanieRating, 5 stars5 days ago
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!
Guest favourite
Townhouse in Allston
4.93 out of 5 average rating, 189 reviews

Sparkling Condo With Modern Amenities

MelissaRating, 5 stars2 weeks ago
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.
Guest favourite
Cabin in Cohasset
4.92 out of 5 average rating, 336 reviews

Lionsgate at Cohasset

TerriRating, 5 stars2 weeks ago
Kao’s home worked great for us. His garden is absolutely beautiful and the area is quite serene. Would definitely stay there again.
Top guest favourite
Home in Melrose
4.96 out of 5 average rating, 110 reviews

Upscale 5BR Family Home Near Boston

DaleRating, 5 stars1 month ago
The home was in a very nice and quiet area of town with groceries, gas and restaurants a short walk or drive away even in during busy hours of Boston traffic. The home was actually larger than expected with two full bathrooms, one on each floor. Everything was clean and ready for us with a well equipped kitchen and filtered water. There was a nice booth area to eat as well as counter seating and a dining room. We only had three in our party, but you could comfortably house a much larger family in the rental. We have a few more trips planned to Boston this year and will book this first if it is available, would like to stay again.
Guest favourite
Flat in East Boston
4.89 out of 5 average rating, 441 reviews

Country Style.Boston Logan Airport & Train 3 bed.

SarahRating, 5 stars2 days ago
Very cute spot, had a great stay here
Top guest favourite
Home in Cambridge
4.93 out of 5 average rating, 103 reviews

Private Apartment. Dog friendly. Parking

JenRating, 5 stars1 month ago
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!!

Family-friendly home rentals with a pool

Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars42 months ago
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!
Guest favourite
Guest suite in Canton
4.71 out of 5 average rating, 108 reviews

Newly renovated, close to Foxboro and Boston

StacyRating, 5 stars2 days ago
Smaranda was outside when we arrived, she greeted us and since it was around dinner time she offered some recommendations for dinner. It had been quite windy that day so the pool and hot tub had some leaves and debris in them. She was very apologetic (obviously not her fault, we can't control Mother Nature) and was very attentive and worked hard to get both the pool and hot tub ready for us to use. She showed us how everything worked and the instructions were clear and easy to follow. We used both the pool and hot tub after we got back to the space after dinner and they were both very nice and relaxing. We enjoyed our stay and everything went as planned. We would definitely stay again if Smaranda would have us! Stacy and Ray
Guest favourite
Flat in Winthrop
4.96 out of 5 average rating, 313 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

BethRating, 5 stars2 weeks ago
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!
Top guest favourite
Guest house in West Roxbury
4.95 out of 5 average rating, 197 reviews

Country Cottage in the City

GraceRating, 5 stars2 days ago
This was such a a delightful place to stay. The surroundings were so beautiful and calm. We were greeted by turkeys, and a mother and newborn deer crossed our path as we left. The hosts, Susan and Mark, were friendly, attentive and accommodating. I would certainly come back in a heartbeat.
Guest favourite
Flat in Holliston
4.96 out of 5 average rating, 121 reviews

Loch Link

ValentinaRating, 5 stars2 months ago
Se fosse possibile avremmo dato 6 stelle! immersi nella natura ma a due passi da ogni comfort, l'alloggio di Michael si è rivelato oltre le nostre aspettative. Istruzioni chiare su tutto e disponibilità dell'host a dare indicazioni e suggerimenti. Scelta come base per la maratona di Boston, questo alloggio si è rivelato perfetto anche per visitare lo splendido New England! lo consigliamo vivamente e speriamo di poter tornare presto!

Quick stats about holiday rentals that are family-friendly in South Boston

  • Total rentals

    150 properties

  • Nightly prices starting at

    $38 SGD before taxes and fees

  • Total number of reviews

    7.2K reviews

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Destinations to explore