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Family-friendly holiday rentals in Randolph

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 20 holiday rentals in Randolph

  • Nightly prices starting at

    Randolph holiday rentals start at £89 per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Randolph holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Randolph rentals

  • 4.8 Average rating

    Randolph stays are highly rated by guests – averaging 4.8 out of 5!

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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Guest favourite
A welcoming entryway showcases a wooden staircase leading to the upper levels. The space is enhanced by decorative topiary arrangements and features light-colored flooring providing a bright ambiance. Natural light emanates from a nearby doorway, revealing glimpses of the outdoor area.
Home in Stoughton

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 abundance on-street parking. Pet friendly!

4.93 out of 5 average rating, 158 reviews
Top guest favourite
A modern dining area features a glass-top table surrounded by four black chairs, positioned over a decorative rug. A colorful wall art piece is displayed nearby, and an electric fireplace adds warmth to the space. Light-colored walls and flooring enhance the ambiance.
Flat in Quincy

“Very Modern Apartment” Dedicated Driveway Parking

Whether you are just getting away for the weekend or looking for an extended stay, we are committed to creating a comfortable experience. Professionally cleaned & sanitized Great customer service High quality linens and towels. Very spacious 1100 sq ft 2 bedrooms and 1 bath unit with high ceiling. Each bedroom features a queen bed with foldable twin beds. Fully stocked with everything you might need for longer comfortable stay. Located in a very nice residential area.Dedicated driveway parking

4.96 out of 5 average rating, 126 reviews
Guest favourite
A modern living area features a stylish orange sectional sofa, paired with decorative pillows. To the rear, the kitchen showcases stainless steel appliances, white cabinetry, and a dining space, while a staircase is visible in the background.
Home in Weymouth

Beautiful 3BR Home by the Water - Family Friendly

Welcome to our newly renovated 3-bed, 2-bath single-family home nestled in a serene and welcoming neighborhood in North Weymouth: • Walk to Wessagusset Beach and George Lane Beach • Just a 2-mile drive to Hingham Shipyard's dining, shops, and commuter boat to Boston • 11 miles from Downtown Boston • 3 miles from commuter rail or subway stations (bus #220, a 2-minute walk, takes you to Quincy Center or Hingham Shipyard) Ideal for families or groups seeking relaxation and easy city access.

4.91 out of 5 average rating, 140 reviews
Top guest favourite
A serene view of the lake at sunset is framed by lush greenery and a manicured lawn. Three blue Adirondack chairs are positioned near the water's edge, offering a perfect spot to enjoy the fading light. The sky displays warm hues reflecting on the calm surface of the lake.
Guest suite in Braintree

Sunset LAKE VIEW studio. Recently upgraded!

Welcome to Sunset Lake! Enjoy beautiful sunsets year round! Cozy in the winter with plenty of extra blankets and a great heating system! Light a fire at night. We are walking distance to South Braintree Square. You will enjoy nature and still have close proximity to city. Walk to a super market, pharmacy, nail salon, bank, a tavern w/ live music. Other restaurants within walking distance include Mexican, Thai, Sushi, Italian, Vietnamese (pho), pizza and a great local coffee shop ☀️ 🌅

4.87 out of 5 average rating, 121 reviews
Top guest favourite
The living room features light-colored sofas and a coffee table placed on a warm area rug. Bright natural light enters through several windows, illuminating the space. A wall-mounted TV is visible, and a stylish coat rack adds a modern touch.
Home in Braintree

Near Boston w/ parking & deck, 3-bedroom home

Bright and cozy space located in Braintree Center, just 10-miles outside of Boston. Our home is an ideal location for families, friends, business travelers, and even wedding parties looking for more space, while also enjoying the proximity to Boston, Logan Airport, and more! Have a wedding, event, or want to see a sunset view of the Boston skyline? Granite Links Golf Course is 4 miles away! Looking to see a concert or Patriots Game at Gillette stadium? Arrive there in just 25 minutes!

4.95 out of 5 average rating, 146 reviews
Guest favourite
A modular queen sofa with light blue upholstery is positioned in a brightly colored living area. Vibrant patterned cushions enhance the seating, while an ottoman and area rug with a similar design add comfort and style. The kitchenette and additional furnishings are visible in the background.
Flat in Randolph

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!

4.86 out of 5 average rating, 136 reviews
Guest favourite
Home in Quincy

5BR-4BA Adams Shore Home FREE Parking & W/D 284

Pet-Friendly 5-Bedroom Coastal Home – Walkable to Marina, Harbor & Wollaston Beach | Perfect for Families & Groups | Easy Downtown Boston Access Why Guests Love Our Home: ★ Five Free On-Site Parking ★ Great Location - Close to restaurants and public transport. ★ First-Floor Bedroom & Bathroom – Elderly-friendly setup ★ Dedicated Workspace – Perfect for remote work ★ High-Speed Wi-Fi ★ Self Check-In ★ Fully Equipped Kitchen ★ Washer & Dryer ★ Fresh Linens & Toiletries Included

4.88 out of 5 average rating, 189 reviews
Guest favourite
Flat in Randolph

1 Bedroom Basement Apartment

Cozy basement apartment in a private home with separate entrance and parking. Features a fully equipped kitchen, bathroom, and living room. Located in Randolph, MA, just south of Boston. 6-minute drive to public transportation (Quincy Adams Train Station). Accessible by car only, so we recommend renting a car or using Uber. Close to local beaches and ski areas for outdoor adventures. Perfect for a peaceful, convenient stay with easy access to Boston and surrounding attractions.

4.88 out of 5 average rating, 370 reviews
Guest favourite
An open living area is illustrated, featuring a light-colored sectional sofa with blue accent pillows. A large flat-screen television is mounted on the wall. A wooden coffee table sits on a patterned area rug, while a dining area is visible in the background.
Holiday home in Randolph

Built 2020 Private Home/4 Beds/2.5 Baths/EV Charge

Kick back and relax in this calm, quiet & stylish single new built home. Within 20-25 minutes driving distance to Boston downtown, Logan International Airport, Encore Casino, China Town, Financial District. 5-10 minutes away from Park & Ride shuttle to The Airport, 110 Grill, Legal Seafood, Five Guys, Starbucks, LA Fitness, Tavern in The Square, Bank of America, AMC movie theater, South Shore Shopping Mall, Chase Bank, BJ or Costco, Kohl’s, Olive garden.

4.96 out of 5 average rating, 116 reviews
Guest favourite
A spacious bedroom features a large bed with a light-colored comforter and decorative pillows. Two lamps provide soft lighting. Mirrored closet doors reflect the room, and artwork hangs on the wall, adding a touch of character. Warm wooden flooring complements the neutral decor.
Home in Canton

Gorgeous 2nd Floor Home with Private Entry

Welcome to your home away from home! This beautiful second-floor 2 BR unit keyless self check in offers a private entrance and private stairs. Features: · Newly Installed AC · Fully Kitchen: Equipped with smart utilities, including an oven, microwave, dishwasher, washer, and dryer. · High-speed internet. · Comfortable Sleeping Arrangements: 2 beds & a sofa bed, perfect for accommodating up to 4 guests.

4.95 out of 5 average rating, 104 reviews
Top guest favourite
A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.
Home in Dedham

Cozy, historic 3 bedroom home close to Boston!

Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.

4.98 out of 5 average rating, 302 reviews
Top guest favourite
A spacious living room is displayed, featuring a large sectional sofa with accent pillows. A coffee table sits atop a textured area rug. A modern fireplace is framed by brick, and a wall-mounted TV offers entertainment options. Natural light is provided through large windows.
Guest house in Foxborough

Bates Boutique ☆ Home Away From Home

Stay at a recently renovated Bates Boutique specifically for your enjoyment. Highlights: - Fully redesigned kitchen & dining area - Relax in the living room with a 65" Smart TV (live channels, Netflix, Disney+, Hulu, Apple+, HBO Max, and others included) - Cozy bedrooms with heavenly bedding - 3 workspaces to ensure you can get work and play done - Outdoor patio & grill for fun inside & out

4.97 out of 5 average rating, 214 reviews

Popular amenities for Randolph family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
A historic stone farmhouse is set on a spacious green lawn, complemented by a vibrant red barn in the background. Tall trees provide shade, and a carefully arranged stone border outlines the lush garden area, creating a tranquil outdoor setting.
Farm stay in Hopkinton

1790 Stone Manor Farm

4.96 out of 5 average rating, 166 reviews
Top guest favourite
An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.
Home in Hopkinton

Hopkinton Mass 3+ Bedrooms - Great location!

4.95 out of 5 average rating, 179 reviews
Top guest favourite
Cottage in Mendon

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

4.95 out of 5 average rating, 154 reviews
Superhost
Home in Somerset

Campfires & Porch Swings Hot Tub | Pets Welcome

4.87 out of 5 average rating, 125 reviews
Guest favourite
A charming living area features two upholstered armchairs with decorative cushions, complemented by a round coffee table. Natural light filters through large windows adorned with wooden frames, illuminating the intricate wood ceiling beams above. A fireplace is situated in the corner, adding warmth to the space.
Home in Providence

Cozy Home next to City Park

4.92 out of 5 average rating, 209 reviews
Guest favourite
Farm stay in North Andover

Winery Farmhouse w/ Private Hot Tub & Wine Tasting

4.97 out of 5 average rating, 132 reviews
Top guest favourite
A spacious wrap-around porch is shown with comfortable seating, offering panoramic views of the waterfront. The warm glow of sunrise reflects on the water, and a distant bridge is visible under a clear sky. The setting invites relaxation and enjoyment of the serene environment.
Home in Somerset

Beachfront W/ Hot Tub, Sauna, Pool & Panoramic View

4.99 out of 5 average rating, 192 reviews
Top guest favourite
A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.
Home in North Andover

Nana-tucket Inn

4.95 out of 5 average rating, 184 reviews

Family- and pet-friendly home rentals

Top guest favourite
The exterior of a spacious guesthouse showcases a blend of siding and stone finishes. A paved driveway leads to a two-car garage. Lush greenery and flower beds enhance the inviting entrance, while multiple windows allow natural light to fill the interior.
Guest suite in Sharon

Cozy Lakeview Guesthouse Near BOS, PVD, Cape Cod

4.96 out of 5 average rating, 232 reviews
Guest favourite
The dining area features a wooden table with six chairs, complemented by a striped table runner. A stylish vase with dried stems is placed at the center. A cozy couch, adorned in rich upholstery, is located beside the table, with a cityscape wall art piece above a dark cabinet.
Home in Hyde Park

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

4.86 out of 5 average rating, 359 reviews
Top guest favourite
A well-maintained yard sits on a spacious acre, featuring lush green grass and a variety of trees. The house is partially visible on the right, and a clear path leads to the sunroom entrance. Flower beds with blooming plants add color to the landscape.
Home in Walpole

Entire home 3 miles from Gillette, sleeps 7.

4.9 out of 5 average rating, 112 reviews
Top guest favourite
An updated kitchen features granite countertops, white cabinetry, and stainless steel appliances. A large island with seating for four is complemented by a dining nook with natural light. Potted plants add a touch of greenery, enhancing the inviting kitchen space.
Flat in Hull

Coastal Cottage Home

4.93 out of 5 average rating, 123 reviews
Guest favourite
Home in Wayland

Spacious 4 bedroom home with large yard

4.9 out of 5 average rating, 132 reviews
Top guest favourite
Apartment in Winthrop

Truly Oceanfront! Spacious Family Petfriendly Home

4.99 out of 5 average rating, 241 reviews
Guest favourite
Flat in Quincy

Beach Home next to Boston & T, King Bed, Park Free

4.93 out of 5 average rating, 197 reviews
Top guest favourite
A charming farmhouse exterior is showcased, featuring a weathered wooden facade and bright blue shutters. A welcoming front porch is adorned with pumpkins, while well-maintained landscaping and a mailbox are visible in the foreground.
Home in Scituate

Cozy, well-equipped beach cottage, steps to beach!

5.0 out of 5 average rating, 149 reviews

Family-friendly home rentals with a pool

Guest favourite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guest house in West Roxbury

Country Cottage in the City

4.95 out of 5 average rating, 217 reviews
Guest favourite
A spacious room features a full-sized bed with light bedding. A euro lounger is positioned in front, decorated with a soft throw. Mirrors on the opposite wall reflect the room's layout, and a window offers natural light, contributing to the overall bright atmosphere.
Guest suite in Rockland

Cozy Private Suite halfway between Cape & Boston

4.87 out of 5 average rating, 114 reviews
Superhost
A serene pool area is surrounded by lush gardens, featuring vibrant flowers in planters. A pool house is visible in the background, framed by greenery. The clear water of the pool reflects the surrounding natural beauty, inviting relaxation and enjoyment.
Home in Plymouth

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

4.9 out of 5 average rating, 198 reviews
Guest favourite
A cozy living area features a spacious daybed flanked by decorative pillows. Two armchairs are positioned across from a coffee table, enhancing the seating arrangement. A decorative vase adds charm beside the fireplace, while natural light filters through the window, illuminating the wood flooring.
Guest suite in Revere

Amazing studio

4.88 out of 5 average rating, 206 reviews
Guest favourite
Flat in Everett

Curated Designer Retreat • Pool • Gym • Dining

4.95 out of 5 average rating, 108 reviews
Top guest favourite
Cottage in Marblehead

Pool Is Open in Sept! Steps from Harbor + Old Town

4.99 out of 5 average rating, 167 reviews
Top guest favourite
A spacious exterior view showcases a two-story light gray house with a brick chimney, set against a backdrop of lush greenery and a mix of trees. A charming barn is visible in the distance, complementing the well-maintained gardens and open lawn.
Flat in Groton

Farmhouse Guest Apartment

5.0 out of 5 average rating, 108 reviews
Guest favourite
A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.
Flat in Brighton

The Murthy : Bright • Spotless • W/D

4.96 out of 5 average rating, 159 reviews

When is the best time to visit Randolph?

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Avg. price£211£178£212£225£274£324£234£220£218£236£222£195
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