Family-friendly holiday rentals in South Boston

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Popular amenities for South Boston family-friendly rentals

Family-friendly home rentals with a hot tub

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
Apartment in South Boston
4.91 out of 5 average rating, 66 reviews

South Boston. Minutes away from Convention Center

LeeRating, 5 stars1 week 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!
Guest favourite
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars8 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.
Superhost
Apartment in Roxbury
4.78 out of 5 average rating, 328 reviews

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

AnneRating, 5 stars3 weeks ago
Alex was helpful chasing off people in the reserved parking space!
Guest favourite
Apartment in Holliston
4.96 out of 5 average rating, 121 reviews

Loch 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!

Family- and pet-friendly home rentals

Guest favourite
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 favourite
Apartment in South End
4.96 out of 5 average rating, 380 reviews

Charming South End Duplex (Pets Ok)

AnnaRating, 5 stars1 week 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 favourite
Townhouse in Allston
4.93 out of 5 average rating, 189 reviews

Sparkling Condo With Modern Amenities

MelissaRating, 5 stars1 week 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
Home in Everett
4.89 out of 5 average rating, 302 reviews

#7 Comfortable Spacious Home Near Boston + Parking

DanielRating, 5 stars2 weeks ago
We went to Boston to attend a college graduation so we rented this house for the family. We were very happy with the home and the location. The house was stocked with all of the basic necessities. It is newly renovated with a great kitchen and was very clean and comfortable. The neighborhood was great for walking, with several small grocery stores and restaurants close. Wally was a very proactive and professional host. I highly recommend staying here.
Guest favourite
Cabin in Cohasset
4.92 out of 5 average rating, 334 reviews

Lionsgate at Cohasset

PritiRating, 5 stars2 weeks 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.
Superhost
Condo in Cambridge
4.86 out of 5 average rating, 104 reviews

#2A MIT & Harvard amazing location!

LisaRating, 5 stars2 weeks ago
Great stay! Perfect for our needs while visiting our son. Cute and comfortable living space, comfortable bed, hot shower, great coffeemaker with pods provided, nice dining table, good location. Really appreciated the offer to check in early/out late, though we didn't end up taking advantage of it. We'll be back!
Guest favourite
Apartment in Cambridge
4.87 out of 5 average rating, 443 reviews

Cambridge Getaway @ Harvard & MIT

JasonRating, 5 stars2 weeks ago
We really enjoyed our visit to Cambridge—the top floor of Kevin's house is spacious and well-appointed and the location is amazing. It's great to be on a beautiful, quiet street (with a free parking space!) and still be able to walk to Harvard Square, Central Square and public transit. The location is also great for EV drivers, as the Cambridge Municipal Garage (two blocks away) offers overnight charging for a very low price. We felt right at home and will certainly consider renting again the next time we need two bedrooms in the Boston area!
Guest favourite
Apartment in East Boston
4.89 out of 5 average rating, 439 reviews

Country Style.Boston Logan Airport & Train 3 bed.

SherryRating, 5 stars2 weeks ago
The place was perfect for our stay. The commute to Cambridge went smoothly and we were close to many attractions in Boston. It was nice to come back to in the evenings after long days, very comfortable.

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
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars8 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 favourite
Apartment in Winthrop
4.96 out of 5 average rating, 313 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

BethRating, 5 stars1 week 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
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 favourite
Apartment in Holliston
4.96 out of 5 average rating, 121 reviews

Loch 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 holiday rentals that are family-friendly in South Boston

  • Total rentals

    150 properties

  • Nightly prices starting at

    $46 AUD 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