
Family-friendly holiday rentals in South Boston
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Top-rated family-friendly rentals in South Boston
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Boston family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Ultra Modern House in Newton ; Boston
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!

South Boston. Minutes away from Convention Center
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!

Newly renovated, close to Foxboro and Boston
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.

Modern, Spacious 1BR for 4 - Easy Marathon Access!
Alex was helpful chasing off people in the reserved parking space!

Loch Link
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

Family Home + Near Downtown + Cool Backyard!
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.

Charming South End Duplex (Pets Ok)
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:)

Sparkling Condo With Modern Amenities
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.

#7 Comfortable Spacious Home Near Boston + Parking
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.

Lionsgate at Cohasset
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.

#2A MIT & Harvard amazing location!
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!

Cambridge Getaway @ Harvard & MIT
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!

Country Style.Boston Logan Airport & Train 3 bed.
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

Luxury Ultra Modern House in Newton ; Boston
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!

Newly renovated, close to Foxboro and Boston
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.

Cody's Place Boston Airport Pool/Beaches ParkFree
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!

Country Cottage in the City
Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.

Loch Link
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
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- Hampton Beach
- Boston Common
- Fenway Park
- Revere Beach
- TD Garden
- Harvard University
- Lynn Beach
- Brown University
- Duxbury Beach
- North Hampton Beach
- New England Aquarium
- Sagamore Beach
- Faneuil Hall Marketplace
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Sandwich Glass Museum
- Good Harbor Beach
- Prudential Center
- Roger Williams Park Zoo
- MIT Museum
- Rye North Beach
- Museum of Fine Arts, Boston
- Oakland Beach