Family-friendly vacation rentals in Randolph

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Randolph 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!
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars1 week ago
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.
Cabin in Falmouth
4.66 out of 5 average rating, 584 reviews

Waterside Guest House

AubreyRating, 5 stars3 days ago
Had a lovely stay here! It’s a really beautiful, charming location close to lots of great shops and restaurants.
Superhost
Townhouse in Mashpee
5 out of 5 average rating, 3 reviews

4th July week! Cape Cod Townhome

DmitryRating, 5 stars82 months ago
The place is great if you don't mind having to drive to a beach or to town. It's spacious and clean. And Ruth is a great host. She was very responsive.
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
Home in East Falmouth
4.9 out of 5 average rating, 60 reviews

Peaceful waterfront home with dock/ hot tub

ConorRating, 5 stars8 months ago
We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!
Superhost
Home in Plymouth
4.87 out of 5 average rating, 79 reviews

Amazing ocean front 3 bedroom

CrystalRating, 5 stars6 months ago
We had a wonderful stay! The house was great! Views were awesome from the top balcony! We wished the bushes and shrubs had been trimmed a little to have a better view from the main level but it was still a nice view from the one area there. House was quite roomy and had everything we needed in the kitchen. There are not tvs in the two spare rooms which would have been good after dinner for our teenagers while winding down after family time. The host is wonderful and communicated great. Overall we had a great family vacation and a good time. The house is nice. Would recommend!

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. 😃😃
Top guest favourite
Cabin in Rockport
4.97 out of 5 average rating, 447 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

AnaisRating, 5 stars2 weeks ago
Our stay at Dogtown Cabin was absolutely wonderful! Julie was consistently available for any questions or concerns and she was kind and welcoming and made sure we had everything we needed. The cabin itself was cozy yet spacious. Plus it was equipped with everything we needed to help make our stay comfortable. They had some great trails on the property and my family had a great time exploring them. The beautiful property is serene and private but close enough to a lot of tourists destinations. And let’s not forget the animals! My son had a great time meeting the horses and chickens. But I will say hands down the best part of our stay were our adorable furry hosts, Darwin and Azore! They greeted us every morning! Hanging out with them made our stay even more special! We honestly can’t wait to come back.
Guest favourite
Condo in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars1 month 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, 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!
Guest favourite
Home in Sandwich
4.93 out of 5 average rating, 212 reviews

Cottage in the heart of the village

ColleenRating, 5 stars2 days ago
Blake added a nice booklet that had things to do in the area!! Which was a very nice touch! The home also had people walking their dogs and cute little restaurants within walking distance with great food! Defiatley worth another stay!
Guest favourite
Apartment 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!
Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 157 reviews

1 of a Kind Pond-Front Home, Minutes from Downtown

WadeRating, 5 stars4 months ago
We loved staying at this lakeside cabin for thanksgiving with family. Beautiful sunsets, great location, charming house. Loved it!

Family-friendly home rentals with a pool

Top guest favourite
Cottage in North Kingstown
4.98 out of 5 average rating, 44 reviews

Vineyards, Newport, Narragansett, In-Ground Pool

VictoriaRating, 5 stars9 months ago
What a wonderful home and host. Check in was easy and flexible as we weren't sure when we'd arrive. We were greeted by all the fixings for stores and everything was well stocked. Main bedroom bed was very comfortable, bathrooms and kitchen were clean as was the pool in the backyard. We had everything we needed and Tricia gave us great local recommendations for shopping, food and things to do. Would highly recommend if you're traveling to the area with a group/family.
Top guest favourite
Home in Plymouth
4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars6 months ago
Marla's vacation home was very lovely. We liked the pictures of her place, but once we arrived we realized that she had remodeled a number of rooms. Each room was updated, very clean and cozy. Marla has made sure that her place is stocked with all of the large and small conveniences that guests would want in a home away from home. The location and the surroundings are stunning, especially with the Fall foliage. One can tell that Marla takes great pride in her beautiful rental. -Mark & Susan G
Top guest favourite
Home in New Seabury
4.91 out of 5 average rating, 54 reviews

Private POOL*New Seabury*3 Bedroom

Jean PaulRating, 5 stars8 months ago
The home was pristine, more than what we could have asked for. Shelly was an amazing host, again, more than we could have asked for. You want a gorgeous home, with a stellar host, in the cape, with a private pool, amazing amenities, on a golf course and very close to the beaches, fun spots for kids, and shops, go to this place.
Superhost
Apartment in North Falmouth
4.79 out of 5 average rating, 108 reviews

Falmouth, Cozy Studio Near Old Silver Beach

Anna GraceRating, 5 stars8 months ago
We had a wonderful weekend stay! The house is located in a quiet neighborhood and the upstairs apartment was very clean. There is quick access to local beaches and restaurants. We would stay again!
Top guest favourite
Guesthouse 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.
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!
Guest favourite
Condo in Falmouth
4.73 out of 5 average rating, 15 reviews

Condo in Falmouth MA

RoberthRating, 5 stars1 week ago
Wonderfull place very peacefull and quiet . Beautiful lake in the Back as well. Patrick was very quick with his responses.overall great experience
Home in Dartmouth
4.86 out of 5 average rating, 35 reviews

Sweet dreams on Elm Street - steps to the village

AndreaRating, 5 stars9 months ago
We can’t say enough about Amy’s place. It was a peaceful home with a beautiful in the ground pool surrounded by amazing gardens. Amy is a very responsive host. We will be back!

Quick stats about vacation rentals that are family-friendly in Randolph

  • Total rentals

    20 properties

  • Nightly prices starting at

    $97 CAD before taxes and fees

  • Total number of reviews

    750 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore