Family-friendly holiday rentals in Milton

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Milton 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 stars40 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!
Superhost
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars6 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
Cottage in Westford
4.92 out of 5 average rating, 37 reviews

Beach & pond cottage ! Westford MA and Boston!

MelanieRating, 5 stars6 months ago
We had an absolute blast on our girls getaway weekend!! The cottage and community were amazing, exactly what we were hoping for and Doug couldn't have been nicer or more helpful. He was always available by text or phone. The cottage was clean, nicely equipped, and a great location!! We will definitely be renting this cottage again on our next trip!!! Thanks for having us... we loved every minute!! 🧙🧙🧙
Superhost
Flat in Roxbury
4.78 out of 5 average rating, 323 reviews

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

GinaRating, 5 stars1 month ago
Alex was an excellent host, responding to my questions and even gave helpful suggestions regarding places to eat etc. Everything was as advertised and the place was very clean.
Guest favourite
Flat in Holliston
4.96 out of 5 average rating, 121 reviews

Loch Link

MichaelRating, 5 stars4 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

Top guest favourite
Home in Wakefield
4.96 out of 5 average rating, 260 reviews

Welcoming 7-room house <15 miles to Boston & Salem

TyroneRating, 5 stars2 weeks ago
Karen was absolutely incredible. She was very responsive, respectful, and accommodating. We very much enjoyed our stay as my team and I were there on business. She was able to take care of us even on short notice. I really couldn’t be happier with her communication, the quality of their home, and the entire experience. Thank you so much Karen for inviting us into your home. This was truly a 12/10 experience. 😃😃
Guest favourite
Flat in South End
4.96 out of 5 average rating, 374 reviews

Charming South End Duplex (Pets Ok)

HelenRating, 5 stars1 week ago
We just a wonderful few days in Boston for the marathon. Maude was the perfect host… we really appreciated the flexibility with check-in and check-out and were so grateful for the provisions left for us, particularly as we arrived late! The location is perfect, it meant that we could explore everywhere in the City on foot. The neighbourhood is particularly great for restaurants and when the sun came out and the temperature rose, the vibe was fabulous. As a previous review mentioned, if you’re looking for a pristine, freshly painted apartment then it’s not for you, but if you like ‘quirky’ and a house with bags of character, (I especially loved the art), then I’d highly recommend.
Guest favourite
Townhouse in Allston
4.93 out of 5 average rating, 186 reviews

Sparkling Condo With Modern Amenities

AllisonRating, 5 stars8 months ago
Michelle was very responsive and great at communicating leading up to our stay. The house was easy to find, good neighborhood, perfectly clean and had everything we needed. Parking was included which was awesome. The T was easy to walk to so we could go downtown every day easily. The host recommendation for Lulu’s Allston was spot on, it was nearby and great. We felt right at home and had a wonderful stay and check out was also easy. Thank you Michelle for hosting a wonderful place!
Top guest favourite
Flat in Concord
4.96 out of 5 average rating, 206 reviews

Mema's Place --Lovely apartment in private home

DarleneRating, 5 stars2 weeks ago
Wonderful and serene place to stay. Lots of room, clean, perfect for two and a puppy. Would definitely recommend.
Guest favourite
Home in South Boston
4.91 out of 5 average rating, 1,091 reviews

Sanitized Modern 3BD private home-near BCEC

LizRating, 5 stars1 week ago
We loved our stay in South Boston - it was perfect for our family of four with two teens. We loved the location and the ability to walk or take public transportation. The townhome was the ideal space for us and the home was just as advertised - very clean with comfortable beds. The laundry was great as well. We did not cook during our short stay, but the kitchen was nice with everything you need. It was also extremely convenient to the airport, which we appreciated the morning we left on an early flight. Tiffany has truly thought of everything - I highly recommend this lovely townhome.
Guest favourite
Home in Beverly
4.95 out of 5 average rating, 152 reviews

Lovely 2 Bedroom Victorian 1.5 Blocks To Ocean!!!

MelanieRating, 5 stars5 months ago
This Airbnb was one of the best we ever had stayed in! Her house was beautiful, cozy and clean! Johanna was a great host and would definitely love to stay here again!!
Superhost
Home in Medford
4.84 out of 5 average rating, 137 reviews

Sunny home minutes from Boston. Free parking.

LaurieRating, 5 stars1 week ago
We spent 3 nights at Elizabeth’s place. We were 5 adults and had enough space for us all! The house is well located, easy to go to the center of Boston to visit. Beds are confortable and neighborhood really calm. Highly recommended!
Guest favourite
Flat in Cambridge
4.87 out of 5 average rating, 438 reviews

Cambridge Getaway @ Harvard & MIT

LindaRating, 5 stars1 month ago
This is an authentic Cambridge home that has been owned by the host's family for multiple generations. Kevin is accommodating, and he generously left some snacks and drinks in the full kitchen for us. Well-stocked kitchen was super convenient for eating breakfasts. Note: there are significant stairs to get into the unit. Once there it's quite spacious. And I love the operable bathroom window. :) Thanks for a lovely stay in a convenient, walkable neighborhood!

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 stars40 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!
Superhost
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars6 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
Flat in Winthrop
4.96 out of 5 average rating, 303 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

StephanieRating, 5 stars1 month ago
Frank went above and beyond to communicate check-in instructions, rules of the Air BnB, had all the thoughtful amenities for a slumbo! Definitely an ideal location for nicer weather with the location! Unfortunately the weather hindered the ability to fully enjoy this experience with the water so close! Would book again with better weather!!!
Superhost
Cottage in Westford
4.92 out of 5 average rating, 37 reviews

Beach & pond cottage ! Westford MA and Boston!

MelanieRating, 5 stars6 months ago
We had an absolute blast on our girls getaway weekend!! The cottage and community were amazing, exactly what we were hoping for and Doug couldn't have been nicer or more helpful. He was always available by text or phone. The cottage was clean, nicely equipped, and a great location!! We will definitely be renting this cottage again on our next trip!!! Thanks for having us... we loved every minute!! 🧙🧙🧙
Top guest favourite
Guest house in West Roxbury
4.95 out of 5 average rating, 193 reviews

Country Cottage in the City

GarryRating, 5 stars6 days ago
Lovely cottage surrounded by countryside: there were ducks, wild turkeys, chipmunks and blue jays in the garden. 5 mins drive from the lovely town of Dedham and 30 mins into central Boston. Cottage is small but beautifully decorated and has everything you need. Mark was super helpful.
Home in Plymouth
4.9 out of 5 average rating, 184 reviews

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

NancyRating, 5 stars6 months ago
The house was perfect for a wedding weekend for our family of 10, including 3 children. The house is spacious, private, and very well equipped. It has everything you might need, including a great selection of toys and books for children. The hosts were super-responsive, answering our questions immediately. After our first day we figured out it was easiest to turn around in the driveway rather than trying to back out onto the busy road. We were sad to leave. Thank you for sharing your wonderful historic home.
Guest favourite
Flat in Holliston
4.96 out of 5 average rating, 121 reviews

Loch Link

MichaelRating, 5 stars4 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!
Guest favourite
Home in Hull
4.96 out of 5 average rating, 23 reviews

Spacious 3-BR Furnished Beach Home

BriannaRating, 5 stars10 months ago
We had a wonderful stay. Perfect place for families with children. So close to the beach with all the beach and home necessities you need while on vacation! Quaint town that was quiet but still has plenty of restaurants to visit. Overall, a great place!

Quick stats about holiday rentals that are family-friendly in Milton

  • Total rentals

    70 properties

  • Nightly prices starting at

    £22 before taxes and fees

  • Total number of reviews

    2.9K reviews

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    70 properties include access to wifi

Destinations to explore