Family-friendly vacation rentals in South Boston

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in South Boston

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Winthrop

4.96 out of 5 average rating, 302 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Top guest favorite

Apartment in Beverly

4.97 out of 5 average rating, 327 reviews

Victorian Near Beaches, 2nd Floor of 2 Family Home

Great location for visiting Boston and the Northshore of MA. Close to Endicott & Gordon Colleges. Very safe residential neighborhood, only a short walk to 3 beaches, seaside park, quick market, steps to coffee shop. 4 miles from downtown Salem, MA, USA. Close to commuter rail inbound to Boston or out to Rockport/Gloucester. Sleeps 4, 2 bedrooms, 1 1/2 baths, fully equipped kitchen, dining rm, living rm, attic loft with platform bed, W/D, front porch for relaxing with private entrance & parking.

Superhost

Home in Wayland

4.78 out of 5 average rating, 486 reviews

Tiny house experience steps from the water!

-Tiny house experience in quiet private neighborhood on its own lot with great backyard & fire pit on private secluded St. -prof cleaned after each guest -High speed internet/ expanded cable -Built in full bed with queen sleeper futon bed that can sleep 2 more -Just a few steps from beautiful Dudley Pond for swimming/fishing and great walking trails Wayland is one of nicest towns in MA yet only a min or two from anything you need and less than half hour from Boston. texts returned instantly

Guest favorite

Apartment in Beverly

4.75 out of 5 average rating, 297 reviews

Salem/Beverly- Explore Boston's North Shore!

Winter deal- 125 pr night. 3 night minimum- stays through 3/15. Bringing the gang to Boston's North Shore? You'll love this unfussy, spacious, apartment in Beverly. Plenty of room for the family! College visits, holidays & more. 1st floor with spacious eat in kitchen. Centrally located on a quiet side street with parking. Walk to beaches, entertainment, a vibrant downtown with a great food scene and just steps from the commuter rail with trains to Boston, Salem or points north!

Guest favorite

Condo in Cambridge

4.89 out of 5 average rating, 138 reviews

#1A Harvard MIT Central location! in unit W/D

WALK to Harvard, MIT and steps to all public trans & blue bikes! Gorgeous fully furnished monthly stays! Great for tourists, visiting nurses, Harvard, MIT fellows, etc! In-unit w/d and full eat in kitchen (granite counters, dishwasher/disposal (all cooking utensils, etc.). Light filled large bay windows living room with custom built in bookshelves & picture book library. Wood floors, AC/WIFI/all utilities included! Pets (yes large dogs too) welcome w. preapproval.

Guest favorite

Condo in East Boston

4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

Welcome to our family home. It's convenient, comfortable, safe, and close to downtown Boston! We have a backyard and open space with a beautiful deck. It's a great place to spend time and enjoy a peaceful outdoor setting in the city. Located in the waterfront neighborhood of Jeffries Point, East Boston. A 5-minute walk to lovely parks and the HarborWalk. And just ONE SUBWAY STOP to downtown Boston. We love Boston - and hope we can share it with you!

Superhost

Apartment in Beverly

4.85 out of 5 average rating, 172 reviews

Huge 1 Bdrm w/ 3 Queen Beds + Sleeper Sofa

Stunning carrara marble on kitchen walls, white quartz ledgewood cap both fireplaces, new hardwood kitchen floor & newly refinished hardwood in Bdrm & Lvrm, new vanity & floor tile in bathroom, newly installed washer/dryer/frig/gas stove. Huge Bedroom w/ 2 Queen Beds + Huge Living Room w/ 1 Queen Bed + 1 Fold-Down Sofa. Good Wifi/Cable TV. Great location! Off-street parking! Eat-in kitchen. Common use deck/yard w/ gas grill.

Superhost

Apartment in Milton

4.85 out of 5 average rating, 119 reviews

Retreat Milton/Boston line (transit close) Pets

The house is tastefully decorated and can accommodate a larger group , sleeps 6-8. 5 min to Boston , 1.3 miles to Central Ave Transit, or bus at end of street. The house is 20 min to Downtown Boston , it is a duplex totally separated for your own privacy. Reasonable alternative to Hotels , perfect for groups going to Convention Center. I recently added mini splits for additional cooling and heating needs , central ac .

Top guest favorite

Home in Brighton

4.97 out of 5 average rating, 163 reviews

Clean, spacious condo just steps from the MBTA

Perfect location for you to rest and relax during your Boston vacation. Located in a great area just 0.2 miles from the Green MBTA B Line, which will take you right to Fenway Park (3.4 mi) or Downtown Boston. The condo is 1.5 mi to Boston College, 3 mi from Longwood Medical area. Located on the top floor of a beautiful, fully renovated Victorian home. Central heat and air! Located on a very safe street in Brighton.

Top guest favorite

Home in Melrose

4.96 out of 5 average rating, 104 reviews

Spacious 5BR Near Boston | Family-Friendly Stay

Experience the best of Boston just 7 miles away in this 5BR, 3BA family-friendly home. Features include a chef’s kitchen, fenced yard, large deck, Smart TV, central A/C, and parking for 3 cars. Families enjoy added perks like Pack ’n Plays, high chairs, stroller, and more. Transit is just 1,000 ft away for easy city access. Perfect for vacations, business trips, or long-term stays. Stylish, peaceful, and fully equipped!

Superhost

Home in Canton

4.83 out of 5 average rating, 168 reviews

3 bedroom impeccable private home, quiet street

Clean, quiet house with 3 bedrooms, full kitchen, fenced in yard, smart TVs (no cable). Quiet, safe, clean neighborhood, close to restaurants, and amazing outdoor destinations (Blue Hills reservation for hiking, swimming, photography, biking, etc), also golf course, horse barns, rock climbing, ice rink and more! Please note, the driveway and yard are shared with the downstairs unit.

Superhost

Apartment in West Newton

4.83 out of 5 average rating, 390 reviews

Airy, Sunny, CLEAN 2 BR in Waltham- 15 min BOS

CLEAN 2 bedroom with updated kitchen (granite counter top) and bathroom. Minutes to vibrant Moody Street for restaurants (great selection range from good old American food to Asian), local homemade ice cream shop, shops and a movie theater. Quiet, convenient location- 15 minutes to Boston and close to Brandeis University, Regis College, Bentley College and Lasell College.

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What guests are saying

Lovely East Cambridge Apartment

4.87 out of 5 average rating, 657 reviews3 days ago

This place was cozy with everything you might need, even toys if you have small children. Jimmy was a very accommodating host; going above and beyond! We were so lucky to have this space for a very reasonable price. We all agreed the beds were comfy too, and it’s not easy to get approval from 4 different adults.

Apartment in Cambridge

What guests are saying

2bed/2bath Apt at Waltham Landing. Middle Unit

4.88 out of 5 average rating, 131 reviews3 weeks ago

Had the chance of spending a few weeks at Mark's place as a temporary accommodation. The apartment is very spacious and comfortable, equipped with everything needed. Location is great, close to the train station, river walks and the famous Moody street. Plenty of parking space. The proximity to the rail line was not an issue as sound insulation was pretty good. Many thanks Mark!

Apartment in Waltham

What guests are saying

Sunny, clean Wollaston 2BR near Red Line and beach

4.94 out of 5 average rating, 157 reviews3 days ago

We had a wonderful stay at Jon and Gina’s place. It is located in a safe, calm, and very walkable location. The unit is very spacious, comfortable, and clean. The metro train station is a short walk away from which one can access locations throughout the greater Boston region. We did not get an opportunity to meet Gina; however, Jon was a very kind, thoughtful, genuine person who was always ready to be of help. We were here during the Boston Marathon extended weekend and we thoroughly enjoyed ourselves.

Apartment in Quincy

What guests are saying

Modern City Triplex!! Close to Center

4.9 out of 5 average rating, 172 reviews2 months ago

This is a fabulous Airbnb for a large group. We were an extended family group of 8, and it was perfect. It's a beautifully furnished old house, with a user-friendly living area on the main floor, and 2 floors of bedrooms upstairs. There is lots of space to gather and enjoy the evening, with a well-stocked kitchen and dining area, which was great for making dinner for 10 people. But with space to get away to the bedrooms if desired. The bedrooms were what we expected, one huge, one small and 2 medium sized, just as described. All comfortable. The 2 bathrooms were great. There was convenient free parking for our 2 cars. It was easy to walk to the T to get into downtown Boston, or easy to drive in. We loved our stay here, and were the envy of our friends! Our only negative is that it was hard to control the temperature, as it is a lovely old house on 3 stories, so the downstairs could be cold or the upstairs too hot, but we worked with it, no problem. We loved our stay, highly recommended

Apartment in Roxbury

What guests are saying

Beverly Farms Apartment “Homeport”

4.94 out of 5 average rating, 675 reviews1 week ago

We had an amazing stay at Homeport! The house was quiet, clean, and had everything we needed for a comfortable visit. The location was perfect, allowing us to easily explore both Salem and Boston. It was the ideal spot for our little celebration before graduation, and we couldn’t have asked for a better experience. Highly recommend!

Apartment in Beverly

What guests are saying

Victorian Charm, Modern Style w/Private Entrance

4.93 out of 5 average rating, 407 reviews1 week ago

Sure! Here’s a polished Airbnb review based on your notes: ⸻ We had a fantastic stay at this Airbnb! The space was private, roomy, and spotless—exactly what we were hoping for. The location was perfect for exploring Boston, and the host was incredibly responsive and helpful throughout our stay. The kitchen was well-stocked and very clean, making it easy to prepare meals. Having both an upstairs and downstairs bedroom and bathroom gave everyone plenty of space and privacy. We especially loved the charming courtyard Highly recommend this spot for anyone visiting the area. We’d absolutely stay here again!

Condo in South End

What guests are saying

1st Flr 2BR unit with parking + steps from train

4.85 out of 5 average rating, 193 reviews2 weeks ago

This was a great stay. Clean and exactly what it looks like in the photos. It was such a relief to find a place that could accommodate our family of 4, my need to telework while I was there, and also be clean and relaxing and close to family in Roxbury. Oh, and having off street parking is so incredibly valuable. Grateful we found this place & we'll definitely be back. There was a little technical difficulty that was no one's fault that delayed our ability to get in. George was responsive, apologetic, and addressed it immediately to our satisfaction. I'm delighted.

Apartment in Jamaica Plain

What guests are saying

LargeDuplex10Beds w/prkg near Downton

4.96 out of 5 average rating, 114 reviews2 weeks ago

Fatima's place was welcoming, clean, and well-equipped. She was extremely accommodating and helpful. I enjoyed the amount of space we had for a large group. The transit nearby was down but they still had busses to accommodate. Definitely an amazing value for what we paid. I'd definitely recommend it for a bachelor party or any large group outing. We couldn't have had a better time!

Home in Dorchester

What guests are saying

House of Three Gables

4.99 out of 5 average rating, 316 reviews1 week ago

We stayed over in Michael’s place for a small overnight girls trip (4 of us) and it was the perfect size! Beds were comfy, everything was clean, and Michael was very proactive in letting us know about checkin beforehand. It’s also in a great location, close to all of the downtown attractions but still in a quiet neighborhood. I’d definitely recommend this place and stay here again!

Apartment in Salem