Family-friendly vacation rentals in South Boston Waterfront

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in South Boston Waterfront

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

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Guest favorite

The exterior of the house features a combination of brick and siding, with large windows allowing natural light to fill the interior. A spacious driveway provides access, complemented by well-maintained landscaping and a second-story balcony overlooking the surroundings.

Apartment in Winthrop

4.96 out of 5 average rating, 303 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

A comfortable living room features a beige sectional sofa and a sturdy wooden coffee table. Natural light enters through multiple front-facing windows, illuminating the patterned area rug beneath. Decorative items are placed on surfaces, creating a welcoming and cozy atmosphere.

Apartment in Beverly

4.97 out of 5 average rating, 330 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

A cozy outdoor space features a stone fire pit surrounded by a paved patio. A wooden bench sits nearby, with a barbecue grill positioned to the left. Lush, manicured shrubs and small trees frame the area, providing a sense of privacy and tranquility.

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

A casual living area features a light blue sofa adorned with floral cushions, complemented by a beige armchair. Natural light filters through two windows dressed with floral curtains. A table holds a decorative lamp, and a neutral-colored area rug sits beneath a coffee table.

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

A cozy reading nook is situated next to a custom-built wooden bookshelf filled with books and decorative items. A rocking chair with a striped cushion invites relaxation. Soft natural light streams in, highlighting the warm wooden floors and the workspace's inviting ambiance.

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

An outdoor space is presented, featuring a wooden picnic table surrounded by a sprawling lawn. A slide is integrated into the landscape, complemented by vibrant greenery and a nearby garden area. Outdoor seating is also visible in the background, enhancing the communal atmosphere.

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 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 .

Guest favorite

A beautifully renovated Victorian home features a distinctive red exterior with large bay windows and a stone foundation. Lush greenery surrounds the entrance, complemented by flowering plants along the walkway. A spacious front porch invites relaxation and enjoyment of the serene neighborhood.

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

The front exterior of the house features a charming porch with white railings and hanging flower baskets. Lush greenery surrounds the entrance, complemented by a stone path and flower beds. A tall lamp post stands by the walkway, enhancing the inviting appearance of the property.

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, 2BA 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. Transut 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

The exterior of a single-story house is depicted, featuring a grassy backyard and a deck. Green plastic chairs are positioned on the lawn. A section of the yard is enclosed by a fence, with trees providing shade in the background.

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

A dining area is presented with a wooden table set for six. A vase filled with vibrant flowers is centered on the table, and natural light illuminates the space through large windows adorned with sheer curtains. A living area is visible in the background.

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.

Top guest favorite

A cozy living space is presented with a blue couch and a gray armchair positioned near a wall-mounted smart TV. A light-colored rug covers the wooden floor, while sheer curtains frame a window, allowing natural light to enter the room.

Apartment in Cambridge

4.8 out of 5 average rating, 668 reviews

MIT/Harvard/Inman- 2 Bedroom Apt.

First floor apartment located in our 2 family home. Located in vibrant and hip Inman Square. 5 minute walk to the New Union Square Green Line T stop. I live in a separate apartment upstairs with my husband and 2 children. City of Cambridge Inspected and Licensed as a LEGAL short term rental apartment. Registration No. STR-14611 with the City of Cambridge,MA