Family-friendly vacation rentals in San Mateo

4.99 out of 5 average rating, 836 reviews

The exterior of a cozy cottage is visible, surrounded by a lush garden filled with various plants and flowers. A stone path leads to the entrance, framed by vibrant greenery. Large windows allow glimpses of the inviting interior, enhanced by a seasonal wreath on the door.

Guesthouse in San Carlos

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

Treehouse in Half Moon Bay

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.

4.99 out of 5 average rating, 146 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.

Superhost

A cozy living area features a chaise lounge and a comfortable armchair, positioned near a vintage-style fireplace. A small desk is set against the wall, illuminated by a nearby lamp. Natural light brightens the space, highlighting the soft area rug and the neutral color palette.

Apartment in San Mateo

4.72 out of 5 average rating, 137 reviews

Gracious Flat in Downtown San Mateo

Don't miss your chance to stay in this historic mansion in downtown San Mateo- with new elegant touches placed throughout the flat, you can enjoy the old with the new. 3 blocks from San Mateo Caltrain, Philz coffee and all that lovely downtown San Mateo has to offer. Includes free parking & shared on site coin-operated laundry facilities. If you're modern urban people who accept noise from the train/other tenants & love the vibrant downtown diversity, this is the perfect place for you.

4.95 out of 5 average rating, 149 reviews

Eichler home w/ fire pit & private backyard

Step into a beautifully preserved 1956 Eichler home in San Mateo's Highlands - where mid-century design, a serene atrium, and a fire pit backyard come together for the perfect Bay Area stay. - Sleeps 6 | 3 bedrooms | 3 beds | 2 baths - Private backyard w/ fire pit, BBQ & 8-person outdoor dining - Wood-burning fireplace & enclosed atrium w/ custom mural - Dedicated private office w/ door - 20 mins to SF | 15 mins to SFO | near Caltrain - In-unit washer & dryer | AC | streaming TV

4.92 out of 5 average rating, 398 reviews

A large window showcases a view of lush trees and a serene outdoor area. Natural light floods the space, enhancing the warm tones of the elegant decor, which includes a small decorative bicycle and a floral arrangement on a nearby table.

Home in Belmont

Hidden French Gem for Fam/Biz~near Caltrain,SFO

Highly welcome respectful travelers to step through the 750ft super quiet European-style private studio with secluded bay view. Curl up in front of the 4K TV for movie nights at this stylish, soundproofed nest with a luxury mattress, washer and dryer! — welcome infant & kids. — Read everything to avoid surprises. — 5 min walks to park, Caltrain/restaurants; 10~13 min drive to SFO/Stanford; 20-25 min SF. — No pets, no smoking/vaping, no party! — book for 3 if need single bed

A dining area features a light wood table surrounded by four upholstered chairs. A decorative bench sits along one side of the table. Two abstract art pieces adorn the wall, and a potted plant adds a touch of greenery in the corner. Natural light enters through a large window.

4.88 out of 5 average rating, 238 reviews

12-Min From SFO, Tastefully Designed, Work Station

Welcome to the Laurel Pad, a home away from home. You'll enjoy the convenience this house offers - fully stocked kitchen, minutes away from amazing restaurants, supermarkets, parks, 13-min to SFO, 25-min to downtown San Francisco, and easy access to major companies around Silicon Valley. This bright and sunny house is tastefully designed and updated to offer functionality and aesthetics. You'll have access to fast wifi and dedicated driveway parking for up to two cars.

4.98 out of 5 average rating, 240 reviews

A cozy living area features a sectional sofa and coffee table, complemented by a 55" smart TV mounted on the wall. A standing desk with dual monitors and a small kitchenette, including a microwave and refrigerator, provide convenience. Three nature-themed artworks adorn the walls.

Guesthouse in San Mateo

Modern guest house in great location

Private 1 bedroom + 1 bathroom with your own entrance. Highlights: • self-checkin with code on digital lock • free parking + additional free street parking • professional cleaning and sanitizing • king size bed with premium mattress and linens • located at end of cul-de-sac in a safe and quiet neighborhood • standing desk with monitor and docking station • high speed WiFi • 55” smart TV • Rainfall shower, bidet toilet with heated seat, heated towel rack, makeup mirror

4.91 out of 5 average rating, 361 reviews

A cozy living area showcases a gray sectional sofa and two accent chairs. A light-colored coffee table is centered on a patterned rug. A television sits on a console, with large sliding glass doors providing natural light and views of the backyard garden.

Guest suite in San Mateo

San Mateo Getaway Private 2 Bedroom

Bright & spacious 2 bedroom apartment with beautiful backyard in San Mateo. In-law apartment with private entrance dedicated to hosting guests. Located in quiet residential neighborhood, but close to activities for families and singles. Amenities include wet bar area with toaster oven, coffee maker, mini fridge and microwave. Easy access to San Francisco/San Jose via 280 & 101. Close to SFO, Cal train/BART and Downtown San Mateo. Lots of street parking.

4.99 out of 5 average rating, 147 reviews

An inviting deck area features two white lounge chairs adorned with pillows, positioned near a door leading into the studio. A light-colored rug lies in front of the entrance, while a wooden railing offers a view of the surrounding greenery.

Guesthouse in San Carlos

Delightful Hideaway in San Carlos

Fully equipped executive studio in the heart of Silicon Valley. This studio is ideal for accommodating executives, visiting doctors and nurses and other professions that might require long term stays. Visitors will enjoy the warm family-friendly environment and delightful garden setting. It is also well-suited for those on vacation who delight in visiting the nearby cities, as well as those who have families close by and want to have their own private spot.

4.93 out of 5 average rating, 313 reviews

Home in Foster City

Lagoonfront Retreat: 3BR House Near SFO

Our stunning Airbnb listing offers both convenience and relaxation. 5min to multiple supermarkets and 15mins to SFO. Enjoy breathtaking views of the lagoon, modern decor, a fully-equipped kitchen, two comfortable living areas, and three cozy bedrooms with high-quality linens. We provide high-speed Wi-Fi, working desks, and heating for your comfort. We look forward to hosting you and helping you make the most of your stay in this beautiful area.

Place to stay in San Mateo

A scenic outdoor area is visible, featuring a trampoline alongside a grassy space. A deck extends toward the water, where a blue kayak and a boat with a cover are stationed. A shaded seating area is located nearby, with a view of the serene lake.

4.89 out of 5 average rating, 131 reviews

Cottage on the Water -SUP,Kayaking,Canoeing

Private Club House Water Front. Free use of stand-up paddle board, kayak, and canoe. Private entrance with Smartlock and wifi. Modern studio with full bathroom. and the kitchenette area is fully furnished for light cooking. Conveniently located near grocery, Target, Trader Joes, and restaurants. 5 minutes from Downtown San Mateo, and 10 minutes from SF Airport. Looking to get away from the bay area without actually leaving, nice escape.

4.89 out of 5 average rating, 145 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

Popular amenities for San Mateo family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

An aerial view showcases a resort-style pool surrounded by lounge chairs and shaded cabanas, set within lush landscaping. Nearby, a patio area with seating is visible, while the modern apartment buildings create a backdrop for this inviting outdoor space.

Apartment in Menlo Park

4.85 out of 5 average rating, 113 reviews

Luxury 2BR Apt near Tech Companies and Stanford

4.97 out of 5 average rating, 208 reviews

A living area features a blue sofa adorned with decorative pillows and a light blue area rug. A white desk with a green chair is positioned against a turquoise accent wall. Soft light is present, illuminating the entrance to the hallway in the background.

Condo in Pacifica

Game room, 20 min to SF, hot tub, beach 1 block

4.88 out of 5 average rating, 284 reviews

Guesthouse in Belmont

Private Garden Cottage Belmont Hills*Pool*HotTub*

4.95 out of 5 average rating, 217 reviews

A dining area features a round table surrounded by four light-colored chairs, positioned near large windows offering panoramic ocean views. Natural light floods the space, highlighting the minimalist decor and the neutral color palette.

Home in Pacifica

Coastal Retreat w/ Ocean Views

4.97 out of 5 average rating, 146 reviews

A secluded outdoor area features a hot tub surrounded by lush greenery. A shaded patio sits nearby with white lounge chairs, while a portion of the building is visible in the background, incorporating large windows and a deck area adorned with outdoor furnishings.

Farm stay in Woodside

Apartment w hot tub / forest & ocean view

4.99 out of 5 average rating, 130 reviews

An expansive living room features a leather sectional sofa, a circular coffee table, and a stone fireplace. Large glass windows provide views of the surrounding greenery, while wooden beams and a rustic stone wall create a natural ambiance. A television is positioned near the sofa.

Home in Mill Valley

Two Creeks Treehouse

Guesthouse in Redwood City

A modern kitchen is highlighted by a spacious granite countertop island with four wooden stools. Natural light pours in through a large window overlooking the garden, illuminating stainless steel appliances and cabinetry. Plants add a touch of greenery to the inviting space.

4.99 out of 5 average rating, 127 reviews

Private Cottage near Redwood City and San Carlos Downtowns

4.96 out of 5 average rating, 661 reviews

Guest suite in Daly City

Romantic Spa Suite—Whirlpool•Sun Deck•Luxe Escape

Family- and pet-friendly home rentals

4.81 out of 5 average rating, 146 reviews

A spacious deck is showcased, featuring a vibrant red umbrella providing shade over a circular table. A hammock with colorful stripes is visible, gently swaying in the sunlight. Surrounding greenery creates a serene backdrop, enhancing the outdoor relaxation spaces.

Home in San Carlos

Canyon Oak House: Private, tranquil with trees

4.98 out of 5 average rating, 255 reviews

The exterior of the cottage features a stone-accented porch with a wooden chair, framed by lush greenery and flowering plants. A pathway of stones leads from the well-kept lawn to the entry, where large double doors invite guests inside.

Cottage in San Carlos

Carmelita Creek House

A spacious living room features large windows allowing for ample natural light. Comfortable seating is arranged with a gray sofa and dark armchairs. A glass coffee table sits atop a plush area rug, while artwork adorns the walls, adding a touch of color to the neutral palette.

4.92 out of 5 average rating, 310 reviews

Serene Modern Home with Yard & Parking

Guest suite in Half Moon Bay

A cozy outdoor seating area features two rattan chairs positioned on a deck. A small table rests between them, with a scenic ocean view visible in the background. Sunrise colors illuminate the sky, and a vibrant pink flamingo adds a playful touch to the greenery.

4.96 out of 5 average rating, 401 reviews

Oceanview Penthouse, Stylish, Walking to Beach

4.97 out of 5 average rating, 365 reviews

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

SkyHigh Redwoods Retreat with Bay Views

4.96 out of 5 average rating, 188 reviews

A bright living room is visible, featuring a comfortable sofa with striped accents, a coffee table made of natural wood, and an inviting fireplace below a flatscreen TV. Large windows provide natural light and views of the outside, complemented by tasteful wall art and decorative elements.

Home in Half Moon Bay

Stairway to Heaven - 2 bedroom

4.94 out of 5 average rating, 160 reviews

Natural light fills the spacious living area, which features a comfortable couch and a round coffee table. Double glass doors lead to a serene patio adorned with greenery, while a dining area with wooden chairs sits opposite a well-equipped kitchen.

Cottage in Redwood City

Adorable Garden Cottage near Stanford

Guesthouse in Redwood City

A shaded porch area features stone flooring and is bordered by lush greenery. Two outdoor chairs and a small table are positioned on the left side, providing a serene spot for relaxation. The entrance to the studio is visible through large glass doors.

4.95 out of 5 average rating, 214 reviews

Charming Studio

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 200 reviews

A charming tiny house is nestled among towering redwood trees, featuring a red door and a large window. Potted plants line the front steps, and a small patio area with red chairs and a table invites outdoor relaxation.

Tiny home in La Honda

Delightful Tiny Home in the Redwoods !

4.95 out of 5 average rating, 106 reviews

A clear blue pool is surrounded by a stone deck, featuring two wooden lounge chairs positioned for relaxation. Lush greenery and palm trees frame the area, providing a natural and serene setting in the private backyard.

Home in San Rafael

Fully renovated private cul-de-sac home in Marin

4.88 out of 5 average rating, 482 reviews

A spacious bed with an intricate patterned cover is positioned in a well-lit room. Towels are neatly arranged on the bed. A colorful piece of wall art adds a touch of character, while natural light filters through a nearby window.

Guest suite in Woodside

Separate entry room near Stanford

4.99 out of 5 average rating, 371 reviews

A rustic cabin is situated among tall redwood trees. A wooden deck extends towards a tranquil pool, which is surrounded by greenery and flower beds. The warm tones of the cabin's exterior complement the natural surroundings, enhancing the serene atmosphere.

Guesthouse in Woodside

Rustic Cabin in the Redwoods

Guest suite in Walnut Creek

A tranquil swimming pool is surrounded by lounge chairs, nestled among lush greenery and tropical plants. The two-story house features large windows, allowing natural light to brighten the space, while a path leads to the garden area.

4.99 out of 5 average rating, 647 reviews

Garden Oasis 1 BR Suite w Spa & Pool, Walnut Creek

4.94 out of 5 average rating, 156 reviews

The interior of the converted school bus features rustic wooden cabinetry and appliances. A spacious teak countertop extends over the cooking area, complemented by a red refrigerator. Sunlight illuminates the living area, showcasing a cozy seating arrangement and large windows with views of the surrounding nature.

Bus in East San Jose

Cozy BUS on Farm Animal Rescue with CITY VIEW

4.94 out of 5 average rating, 444 reviews

An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.

Home in Los Altos

Luxury Silicon Valley Wellness and Work Oasis