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Family-friendly vacation rentals in South Boston Waterfront

Find and book unique family-friendly homes on Airbnb

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Popular amenities for South Boston Waterfront family-friendly rentals

Family-friendly home rentals with a hot tub

An open-concept kitchen and dining area features modern furnishings, including a long dining table surrounded by black chairs. Large windows offer views of greenery, allowing natural light to fill the space. A sleek kitchen island with bar stools complements the contemporary design.
Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars41 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
A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars2 weeks ago
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.
Guest favorite
The kitchen features modern cabinetry and high-end stainless steel appliances, including a refrigerator and microwave. A dark countertop extends to a breakfast bar with two white stools. Warm hardwood floors and soft overhead lighting create an inviting cooking space.
Apartment in South Boston
4.91 out of 5 average rating, 66 reviews

South Boston. Minutes away from Convention Center

LeeRating, 5 stars4 days 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
A spacious backyard is shown, featuring a wooden playset with a slide and swings. Lush greenery surrounds the yard, with tall trees providing shade and privacy. The grass is well-maintained, creating a suitable area for outdoor activities.
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars7 months ago
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.
Guest favorite
A charming red cottage is set against a backdrop of lush greenery. A golf cart is parked on the gravel driveway beside an outdoor canoe. The cottage features a sun-filled porch with multiple windows, inviting natural light into the space.
Cottage in Westford
4.92 out of 5 average rating, 39 reviews

Beach & pond cottage ! Westford MA and Boston!

KatherineRating, 5 stars4 weeks ago
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.
Superhost
The open layout showcases a living area with a comfortable sofa and decorative pillows. A granite counter separates the kitchen from the space, which features natural light from large windows adorned with light-filtering shades. A piece of framed art and a potted plant complete the ambiance.
Apartment in Roxbury
4.78 out of 5 average rating, 327 reviews

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

KatieRating, 5 stars1 month ago
Alex’s place was wonderful and a perfect location for someone who wants to travel Boston on foot. Very close to the T which made getting around really easy. Alex was also a very flexible, responsive, and kind host for our stay. Would definitely stay there again!
Guest favorite
A serene swimming pool is surrounded by lush greenery, with a rock feature and vibrant lounge chairs in various colors. A shaded seating area with an umbrella is visible, reflecting tranquility and inviting relaxation.
Apartment in Holliston
4.96 out of 5 average rating, 121 reviews

Lake Link

ValentinaRating, 5 stars1 month 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!

Family- and pet-friendly home rentals

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!

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 favorite
A sitting area features a classic blue wall with two framed botanical prints above a marble fireplace. An orchid in a pink pot and a small potted plant add color. A comfortable armchair and a leather sofa complete the cozy layout, enhancing the inviting atmosphere.
Apartment in South End
4.96 out of 5 average rating, 379 reviews

Charming South End Duplex (Pets Ok)

AnnaRating, 5 stars3 days ago
Wow! What a surprise gem in the heart of South End. The bakery, the restaurants, the book store, and wine and cheese shop across the way was AMAZING! I can't wait to come back and stay longer. Maude stocked the house with all the essentials and a few treats for us to enjoy at the house. I highly recommend staying here:)
Guest favorite
A comfortable living area is presented, featuring a flat-screen television mounted on the wall. A wooden coffee table and a soft rug complement the space. A small dining setup with a round table and two chairs is visible, illuminated by natural light from a nearby window.
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
A welcoming living room is equipped with two comfortable sofas, a wooden coffee table at the center, and a wall-mounted TV. Natural light enters through multiple windows, while a modern electric fireplace adds warmth to the space, enhanced by a vibrant area rug.
Townhouse in Allston
4.93 out of 5 average rating, 188 reviews

Sparkling Condo With Modern Amenities

MelissaRating, 5 stars3 days 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
A modern living area features two stylish sofas, a round coffee table, and a television displaying a scenic landscape. A cozy hanging chair is positioned nearby. Natural light fills the space through large windows, and a ceiling fan adds to the comfort.
Home in Everett
4.89 out of 5 average rating, 301 reviews

#7 Comfortable Spacious Home Near Boston + Parking

MikeRating, 5 stars1 month ago
We had a great time here, definitely a diamond in the rough! Everything is exactly listed as described and was very easy for us to get around. The rooms were very spacious and plenty of space to park our cars. It was alot of our groups first time coming to visit Boston and do thing in the city which was a very short drive to and in the evening there were so many nice local spots to eat at, awesome memories for sure! Wally is a great Host who will communicate with you and check in with you to make sure you are doing good definitely in good hands. Thank you Wally for hosting our group with an amazing first trip to MA and to alot more future trips!
Guest favorite
A newly remodeled kitchen features modern stainless steel appliances and ample counter space. White cabinetry contrasts with warm wood paneling and flooring. A dining area with a wooden table and chairs is visible, along with soft lighting from pendant fixtures above.
Cabin in Cohasset
4.92 out of 5 average rating, 334 reviews

Lionsgate at Cohasset

PritiRating, 5 stars1 week ago
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.
Guest favorite
Natural light fills the living room, featuring a cozy day bed and a green plant beside it. A decorative wooden sliding door adds character, while a wall sign displays the word 'BELIEVE.' Light hardwood floors enhance the space's warmth.
Apartment in East Boston
4.89 out of 5 average rating, 437 reviews

Country Style.Boston Logan Airport & Train 3 bed.

DaveRating, 5 stars2 weeks ago
What a wonderful unit in a beautiful part of Boston. Beautiful decor and plenty of room for the whole family. Only minutes away from transport into the centre of Boston and the Airport. Elisangela is an amazing host who was very responsive to any queries we had.
Guest favorite
A kitchen countertop with wooden cabinetry is displayed, featuring a vase with flowers, snack packets, and a trash can. Below, a pet feeding station with two stainless steel bowls is observed on a mat, indicating a well-equipped space for furry guests.
Apartment in Ipswich
4.87 out of 5 average rating, 292 reviews

Ipswich Apartment

NatalieRating, 5 stars3 days ago
Molly was incredibly responsive and so friendly! We felt very at home and the space was perfect for our weekend stay. Easy to walk right into town too!

Family-friendly home rentals with a pool

An open-concept kitchen and dining area features modern furnishings, including a long dining table surrounded by black chairs. Large windows offer views of greenery, allowing natural light to fill the space. A sleek kitchen island with bar stools complements the contemporary design.
Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars41 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
The backyard features a tranquil swimming pool with sunlit reflections, surrounded by elegant outdoor seating arranged on a stone patio. Large windows in the main house offer views of the inviting outdoor space, enhancing the serene atmosphere.
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars2 weeks ago
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.
Superhost
A spacious backyard is shown, featuring a wooden playset with a slide and swings. Lush greenery surrounds the yard, with tall trees providing shade and privacy. The grass is well-maintained, creating a suitable area for outdoor activities.
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars7 months ago
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.
Guest favorite
A spacious outdoor area features a crystal-clear pool surrounded by a paved deck. Several lounge chairs are positioned nearby for relaxation. The house in the background displays a welcoming design with a cozy porch. Lush greenery provides a serene backdrop to this inviting space.
Apartment in Winthrop
4.96 out of 5 average rating, 313 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

BethRating, 5 stars6 days 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!
Guest favorite
A spacious outdoor pool area is surrounded by lounge chairs and tables, offering a relaxing atmosphere. The pool is clear and inviting, with steps leading into the water. A rustic building with large windows is positioned nearby, set against a backdrop of lush greenery.
Cottage in Westford
4.92 out of 5 average rating, 39 reviews

Beach & pond cottage ! Westford MA and Boston!

KatherineRating, 5 stars4 weeks ago
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.
Top guest favorite
A light yellow cottage is positioned adjacent to a spacious swimming pool, surrounded by lush greenery. The pool features a diving board and a decorative tile border. Two lounge chairs sit nearby, while steps lead up to the entrance of the cottage.
Guesthouse in West Roxbury
4.95 out of 5 average rating, 196 reviews

Country Cottage in the City

JulieRating, 5 stars1 week ago
Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.
Guest favorite
A tranquil outdoor pool area is surrounded by lush greenery, featuring a swimming pool with a waterfall. Colorful chairs in pink and turquoise are positioned nearby, inviting relaxation. A hot tub is situated adjacent to the pool, contributing to the serene atmosphere.
Apartment in Holliston
4.96 out of 5 average rating, 121 reviews

Lake Link

ValentinaRating, 5 stars1 month 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 vacation rentals that are family-friendly in South Boston Waterfront

  • Total rentals

    50 properties

  • Nightly prices starting at

    G$8,368 GYD before taxes and fees

  • Total number of reviews

    2.7K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore