Family-friendly holiday rentals in Randolph

Find and book unique family-friendly homes on Airbnb

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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Superhost

Home in Stoughton

4.95 out of 5 average rating, 125 reviews

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and unlimited on-street parking. Pet friendly!

Superhost

Guest suite in Dover

4.97 out of 5 average rating, 284 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

Superhost

Apartment in Dedham

4.83 out of 5 average rating, 196 reviews

Lovely townhouse apartment minutes from Boston

Book your stay at this peaceful and centrally-located townhouse-style apartment just minutes from Boston. This newly renovated space features 2 bedrooms (one queen bed and one twin bed), one full bath (second floor), cozy living room with pull out sofa, and eat-in kitchen. Take advantage and relax by the outdoor fire pit (reservations required) or walk to Dedham Square for delicious food and shopping. Dates you need not available? Make sure to check out our other listing just next door!

Superhost

Place to stay in Sherborn

4.97 out of 5 average rating, 310 reviews

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Superhost

Apartment in Randolph

4.85 out of 5 average rating, 117 reviews

TLC Boston- private unit in family home.

One bedroom unit, with a well decorated open space living room area. Queen bed and queen modular sofa and optional air bed. 15 miles from Logan Airport and located just .2 miles once you exit the highway. Convenient highway access to Boston, Foxboro Stadium, and Cape Cod. Short distance to the Blue Hills hiking trails, shopping mall, shopping centers, and restaurants. Few blocks walk to bus stop to access public transportation into Boston. A diverse community and family friendly!

Superhost

Home in Quincy

4.97 out of 5 average rating, 149 reviews

Artist's Haven (2)

Explore Quincy/Boston from my spotless home! As a Superhost, I'm committed to providing a memorable stay to earn your 5-star review. Experience a vibrant, artsy, and tranquil environment that mirrors my passion for art. This immaculate, peaceful 1-bedroom apartment on the SECOND floor is crafted for a perfect energy flow—a sanctuary of creativity, designed, and adorned with my original artworks, adding a unique and inspiring touch to every corner. Certificate # STR-23-8

Superhost

Guest suite in North Weymouth

4.82 out of 5 average rating, 271 reviews

Lovely studio on the coast! Beach close by!

Wonderful location located in north Weymouth. Quiet, Spacious studio apartment. Outdoor deck with patio furniture. Plenty of space for 3 guests max. - Walking distance to George lane beach & Wessagusset beach. - Convenience store, Pizza & Sandwich shop on our block. - 2 miles to Hingham shipyard - 5 miles to Nantasket beach - In between several commuter rail stations and across the street from a bus stop. - 4 miles to Quincy center - 30 minute drive to Boston!

Superhost

Guest suite in Abington

4.88 out of 5 average rating, 334 reviews

South Shore Luxury Apartment

Luxury in-law suite with new appliances, new bed and bedroom furniture, heated bathroom floors, jacuzzi tub, electric fireplace, and off street parking just steps from your own private entrance nestled into the Ames Nowell State Park. Just minutes away from the South Shore Hospital, make this your home away from home! FireTV, Echo Studio, Wii console & games in living room for guest use. 2 hours Early Check-in/Late Check-out available $30

Superhost

Apartment in Randolph

4.88 out of 5 average rating, 343 reviews

1 Bedroom basement apartment

Apartment is in a basement of a one family house with a separate entrance and parking. Includes a private kitchen , bathroom and living room. located in Randolph Ma South of Boston,6 minutes to public transportation reachable only by car since you can only get there by taking the highway. We recommend our guests to rent a car or use uber. Closest train station is Quincy Adams Train Station, beaches , ski area

Superhost

Guesthouse in West Roxbury

4.95 out of 5 average rating, 200 reviews

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. Besides the pool, there are two garden ponds where we keep decorative fish, and a regular parade of various types of birds and even wild turkeys and deer.