Family-friendly holiday rentals in San Mateo County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in San Mateo County

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite

Home in Half Moon Bay

4.91 out of 5 average rating, 417 reviews

Poplar Beach Getaway: Family-Friendly, Near Beach!

Family-friendly, relaxed home in a quiet residential neighborhood - 1/2 block from the blufftops, a 10-minute stroll to lovely Poplar Beach, and 1/2 mile from scenic Main Street restaurants, shops, and cafes. 3 bedrooms with queen beds, two baths, a living area, a well-equipped kitchen, a spacious kid-friendly den, and a backyard with a new deck ensure you all have room to spread out and relax after a fun day at the beach or exploring the area. Short drive to San Francisco, Santa Cruz, San Jose.

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Guest favourite

A serene outdoor space features a swimming pool surrounded by lush vegetation and a gently sloping waterfall. Steps lead from the house to the pool area, with a slide positioned nearby. A vineyard is visible in the background, enhancing the tranquil setting.

Home in Portola Valley

4.93 out of 5 average rating, 180 reviews

3 BR Home on Vineyard nr Palo Alto & Stanford

Professionally cleaned detached home nestled among an oak grove, waterfall & vineyard in the hills above Stanford (10 min), Palo Alto (20 min), Menlo Park (10-20 min), Mountain View (25 min) and San Francisco and San Jose. Perfect for families and groups; staycations, off-sites or startups visiting Silicon Valley . See resort-style amenities below. LATEST UPGRADES: better AC, faster internet & WiFi6 for lots of devices & bandwidth. Pickleball lines on tennis court; putting green w/ remote tees.

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Top Guest favourite

A spacious deck is depicted with comfortable wicker seating arranged around a light-colored table. Lush greenery is observed in planters, enhancing the natural ambiance. Sliding glass doors provide a view into the indoor living area, inviting the outdoors inside.

Guesthouse in Woodside

4.94 out of 5 average rating, 219 reviews

A beautiful Tree house -your own retreat

This charming 2 bedrooms is nestled among the trees in beautiful Woodside, California. This town is 30 minutes from San Francisco and right behind Stanford University. Our tree house is a private, peaceful, modern and a very comfortable detached guest house. The house has a fully equip kitchen, BBQ and very peaceful settings, enjoy nature hikes and be surrounded by peaceful trees and yet just minutes away from town. If your days are not available try airbnb.com/h/woodsidebestplacetostay

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Guest favourite

A bright interior space features large windows allowing natural light to fill the area. Colorful cushions in various shades are arranged on the floor, complemented by wooden accents and an open ceiling design that highlights the natural surroundings.

Treehouse in Half Moon Bay

4.99 out of 5 average rating, 157 reviews

Paradise Treehouse & Heavenly Cabin

A soulful and energetic paradise. Beautiful, private, peaceful & wild surroundings complimented with modern luxuries and comfort. A stunning, unique, & unrivaled experience sure to impact you deeply. Soak in the outdoor tub while you plan your next adventure. Just minutes from the beach, amazing hiking, views and biking. Outfitted with organic latex mattresses, down comforters, top of the line appliances, smoking fast internet and a spectacular wifi sound system with world class acoustics.

FamilyIndoor spacesOutdoor spaces

Top Guest favourite

Tall redwood trees rise from the forest floor, creating a serene canopy. A distant view of the bay is visible through the trees, with a blanket of clouds resting over the landscape. The sky is clear, contrasting with the lush greenery of the forest.

Guesthouse in Woodside

4.97 out of 5 average rating, 383 reviews

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

Indoor spacesFamilyAccess

Top Guest favourite

A spacious living room features a large sectional sofa adorned with accent pillows. A coffee table sits at the center, complemented by a patterned area rug. Natural light floods in through the large windows, highlighting the wooden beams on the ceiling and the stone fireplace.

Home in Half Moon Bay

4.94 out of 5 average rating, 226 reviews

5 min walk to Beach, Sleeps 11, perfect for family

Welcome to our beach house in the beautiful Half Moon Bay! Our 2 story home is located in the family-friendly Alsace Lorraine neighborhood, it's perfect for a memorable family vacation. It's 1 block from the scenic coastal bluff trail & Half Moon Bay State Beach. Downtown is a few minutes walk to restaurants, shops & cafes or simply chill on the beach & watch grey whales or dolphins. Each bedroom also has an office desk to make our home an ideal location for working remote.

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Guest favourite

A spacious grassy yard is surrounded by lush gardens, showcasing colorful flowers and greenery. A seating area with wooden chairs is situated near a fountain, providing a tranquil spot to enjoy the views. The sky displays varying shades of blue, contributing to the serene atmosphere.

Home in Half Moon Bay

4.86 out of 5 average rating, 339 reviews

Oceanfront w/ Direct Beach Access + New Hot Tub

This private oceanfront retreat offers direct beach access, lush gardens, and a spacious lawn. Walk to restaurants, music venues, and galleries nearby. Relax in the hot tub with ocean views or gather around the fire pit at sunset. Surfer’s Beach and Princeton Harbor are just north, and the Coastal Trail passes by for scenic biking and walking. Enjoy surfing, golfing, horseback riding, swimming—or simply unwind with a cocktail while watching the sunset.

Indoor spacesFamilyQuiet

Top Guest favourite

A rustic caboose, painted in bright red, is nestled among lush green trees. Vintage machinery, featuring large wheels and a copper detail, is positioned nearby, surrounded by a gravel area. The ambiance is quietly rural, under the canopies of towering redwood trees.

Train in Cupertino

4.94 out of 5 average rating, 464 reviews

Caboose in the redwoods just outside of Cupertino

This rustic caboose is just 10 minutes from Cupertino and downtown Saratoga, perfect for both business travelers, outdoor adventurers, and everything in between. There are lots of nearby hiking and biking trails, as well as other exciting outdoor activities. Being so close to Silicon Valley, yet feeling so far from it all is a truly unique experience unlike anywhere else. Pets generally ok. Check with hosts. Pets must not be left alone.

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Top Guest favourite

Home in San Mateo

4.9 out of 5 average rating, 153 reviews

SFO 10 Min • Family 2BR + Patio Games • Baby-Ready

Two queen bedrooms, a private patio with lawn games, an in-unit washer/dryer, and a baby-and-toddler setup that covers everything from crib to high chair — this is the Bay Area family home you've been searching for. Ten minutes from SFO, a block from groceries and restaurants, and a short walk to Seal Point Park's waterfront trails, it's the kind of place where you actually unpack and settle in, not just sleep between activities

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Superhost

The image showcases a modern Airstream parked on a sandy area overlooking the ocean. A large retractable awning extends over an outdoor seating arrangement that includes a fire pit surrounded by chairs. Lush green grass and a wooden fence frame the scene, highlighting the coastal setting.

Campervan/RV in Half Moon Bay

4.95 out of 5 average rating, 241 reviews

Beachfront California Coast Airstream_Luxury (NEW)

This spectacular location comes fully equipped with the 'top of the line' 28 foot' Airstream, (Big Sur & Tommy Bahama class limited edition) with horizontal flip rear tail door for seamless indoor/outdoor living. Overlooking a stunning beach, perched high on a cliff this one of a kind experience boasts breathtaking views of the California coastline and Pacific Ocean to create an unforgettable magical experience of a lifetime.

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Top Guest favourite

An open-concept living area is highlighted by a wood-burning fireplace with a textured white surround. Mid-century furniture, including a leather sofa and colorful chairs, is arranged around a plush area rug, while large windows provide natural light and views of the outdoor space.

Home in San Mateo

4.95 out of 5 average rating, 154 reviews

Eichler Home w/ Fire Pit & Private Backyard

Welcome to a beautifully renovated 1956 Eichler home in San Mateo - mid-century character with all the comforts of today. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & 8-person outdoor dining - Enclosed atrium w/ custom mural & red maple tree - Dedicated home office w/ door & fast Wi-Fi - Wood-burning fireplace & open-concept living - 20 mins to SF | 15 mins to SFO | Near Caltrain

KitchenIndoor spacesHospitality

Top Guest favourite

A spacious bedroom features vaulted wooden ceilings and large glass sliding doors leading to an outdoor deck. A comfortable bed is flanked by two bedside tables with lamps. A decorative painting hangs above the bed, and a wooden dresser adds functional storage.

Guesthouse in Woodside

4.99 out of 5 average rating, 593 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

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