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Family-friendly vacation 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

Apartment 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 favorite
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 favorite
Apartment 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
Apartment 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 favorite
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 favorite
Condo in Cambridge
4.88 out of 5 average rating, 101 reviews

#3A-Cambridge Walk to MIT+Harvard Amazing Location

ErenRating, 5 stars3 months ago
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.
Guest favorite
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 favorite
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.
Guest favorite
Apartment in Cambridge
4.87 out of 5 average rating, 444 reviews

Cambridge Getaway @ Harvard & MIT

MarkRating, 5 stars3 days ago
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.
Guest favorite
Apartment in East Boston
4.89 out of 5 average rating, 440 reviews

Country Style.Boston Logan Airport & Train 3 bed.

LynetteRating, 5 stars1 week ago
This was a great place to stay! Very responsive host!
Top guest favorite
Home in Cambridge
4.93 out of 5 average rating, 102 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!!
Superhost
Apartment in Coolidge Corner
4.84 out of 5 average rating, 487 reviews

★Location ★ Walk to Subway ★ One free parking spot

ToddRating, 5 stars1 week ago
This was a great place in a great location! You can walk to restaurants or hop on the green line train right across the street. They are very responsive and everything was as advertised in the listing. Will definitely stay here if I am ever back in Boston!

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 favorite
Guest suite in Canton
4.71 out of 5 average rating, 108 reviews

Newly renovated, close to Foxboro and Boston

StacyRating, 5 starstoday
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 favorite
Apartment 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 favorite
Guesthouse in West Roxbury
4.95 out of 5 average rating, 196 reviews

Country Cottage in the City

JulieRating, 5 stars2 weeks ago
Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.
Guest favorite
Apartment in Holliston
4.96 out of 5 average rating, 121 reviews

Lake Link

MichaelRating, 5 stars5 months ago
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!

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

  • Total rentals

    150 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 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

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