
Family-friendly vacation rentals in Randolph
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Top-rated family-friendly rentals in Randolph
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
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Popular amenities for Randolph 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!

Hopkinton Mass 3+ Bedrooms - Great location!
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.

Waterside Guest House
Had a lovely stay here! It’s a really beautiful, charming location close to lots of great shops and restaurants.

4th July week! Cape Cod Townhome
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.

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.

Peaceful waterfront home with dock/ hot tub
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!

Amazing ocean front 3 bedroom
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

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

The Solar Powered Dogtown Cabin at Applecart Farm
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.

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)
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.

Sparkling Condo With Modern Amenities
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!

Cottage in the heart of the village
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!

Cambridge Getaway @ Harvard & MIT
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!

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

Vineyards, Newport, Narragansett, In-Ground Pool
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.

Our families slice of heaven
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

Private POOL*New Seabury*3 Bedroom
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.

Falmouth, Cozy Studio Near Old Silver Beach
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!

Country Cottage in the City
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.

Spacious 3-BR Furnished Beach Home
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!

Condo in Falmouth MA
Wonderfull place very peacefull and quiet . Beautiful lake in the Back as well. Patrick was very quick with his responses.overall great experience

Sweet dreams on Elm Street - steps to the village
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
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- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- Brown University
- New England Aquarium
- Sandwich Glass Museum
- Faneuil Hall Marketplace
- Sagamore Beach
- New Silver Beach
- Prudential Center
- Freedom Trail
- Onset Beach
- Good Harbor Beach
- Crane Beach
- Symphony Hall
- Roger Williams Park Zoo
- Oakland Beach
- Boston Public Library
- Scusset Beach
- Pinehills Golf Club
- South Shore Beach
- Aaronap Cellars
- Minot Beach