Family-friendly vacation rentals in San Mateo

4.96 out of 5 average rating, 165 reviews

An A-Frame cabin is surrounded by lush greenery, positioned on elevated ground. A stone pathway leads to the entrance, flanked by wooden railings. The cabin features large glass panels on its façade, allowing natural light to flood the interior. A deck with seating overlooks the nature surroundings.

Cabin in Felton

Santa Cruz A-Frame

This unique A-Frame cabin, in a quiet mountain neighborhood with private creek access, was handbuilt in 1965 and remodeled in the summer of 2024. Now a little slice of heaven on the creek in the redwoods. *5-10 min to Henry Cowell Redwoods State Park, Roaring Camp Railroad, Loch Lomond Recreation Area, the Trout Farm Inn, Quail Hollow Ranch + Felton stores. *20 min to Santa Cruz, beach + Boardwalk. *1 min to Zayante Creek Market (EV charger) Find us on social: Insta @SantaCruzAFrame

4.97 out of 5 average rating, 117 reviews

A bright living room features a spacious white sectional sofa adorned with textured pillows, accompanied by a round coffee table. Large windows with shutters allow natural light to fill the space, creating an open atmosphere. A flat-screen TV is mounted near a modern fireplace, complemented by decorative plants.

Home in Foster City

High Ceilings! Modern Spacious Bright 4BR Home

A Hidden Gem! Spacious, tastefully designed, newly renovated modern home on a charming cul-de-sac in Foster City. Ideal open layout with 16ft vaulted ceilings, abundant natural light, expansive backyard with grill and full amenities, making for a great space to entertain and unwind in comfort & style. Centrally located between San Francisco & Silicon Valley. Close to SFO airport, caltrain, restaurants, markets, San Mateo, Stanford, Palo Alto. Perfect for business travelers or family vacations.

4.99 out of 5 average rating, 829 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.

4.72 out of 5 average rating, 134 reviews

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

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.

4.93 out of 5 average rating, 108 reviews

SFO 10 min, Stylish Suite, Walk to Grocery

Ten minutes to SFO, a short walk to Caltrain, and one block from cafés and restaurants— this private San Mateo suite is the ideal Bay Area base for business travelers, airport transits and couples exploring the peninsula. Settle into a comfortable queen bed with room-darkening shades, pull up a dedicated workspace with 789 Mbps WiFi, and unwind with Netflix, HBO Max, Disney+, Hulu, or Amazon Prime on the smart TV. Everything is taken care of so you can focus on why you're here.

4.79 out of 5 average rating, 108 reviews

The studio features vaulted wooden ceilings and a spacious layout. A king bed is positioned near a large window, providing natural light. A smart TV is placed on a stand, while a kitchenette can be seen in the background, equipped with modern appliances.

Guest suite in San Mateo

246C - Large Studio w/ Kitchenette, Laundry & Deck

This is a spacious, modern, and newly remodeled studio unit in our beautiful home located in the center of Hillsdale. This studio features a king bed, smart TV, private bathroom, large kitchenette and wet bar, in-unit laundry, and a spacious SHARED deck with the main unit. It is 2 blocks from San Mateo Medical Center, and only a mile away from Hillsdale Shopping Center & Traders Joe's. There are many restaurants & shops nearby. This studio is accessed from the backyard deck

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.

4.87 out of 5 average rating, 230 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.

4.99 out of 5 average rating, 235 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

4.98 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

The creek house is on a beautiful tree lined street, walking distance to downtown San Carlos. The house is a spacious one bedroom cottage with designer finishes and vaulted ceilings. You will be surrounded by mature redwoods and nature overlooking a year round creek. Amenities include a full sized kitchen, workspace, washer/dryer, fast WiFi, cable TV and a gas fireplace. Please note the cottage is located behind our main home and is accessed via several steps.

An outdoor seating area features a spacious table surrounded by ten chairs, complemented by a cozy texture of orange cushions on a wicker sofa. A fire pit occupies the center, with a sunshade above to provide comfort during warm days.

4.85 out of 5 average rating, 112 reviews

Relaxing Backyard Retreat -Spacious + Bright Home

Escape, relax, and recharge at our beautiful 3-bedroom, 2-bath retreat in San Mateo, perfectly designed for families, friends, and remote workers seeking comfort and convenience. Featuring a modern open-concept layout, this spacious home is ideal for gathering, entertaining, or unwinding in style. Step outside to your private backyard oasis with lush greenery, a cozy patio, and glowing string lights,the perfect spot to enjoy peaceful Bay Area evenings.

4.93 out of 5 average rating, 310 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.

A private backyard scene features a wooden deck with a circular table and an outdoor sofa amid lush greenery. Tall grasses sway gently in the breeze, while nearby trees provide a natural backdrop under a clear blue sky.

4.95 out of 5 average rating, 147 reviews

Eichler home w/ fire pit & private backyard

Step into a piece of Bay Area history. - 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 office w/ door - ideal for remote work - Wood-burning fireplace & open-concept living - 20 mins to SF | 15 mins to SFO | near Caltrain As of 6/12/26 there is one parking spot in the driveway, if you need two, let us know before check in

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

4.88 out of 5 average rating, 283 reviews

Guesthouse in Belmont

Private Garden Cottage Belmont Hills*Pool*HotTub*

4.94 out of 5 average rating, 157 reviews

A secluded hot tub is surrounded by lush greenery and towering redwoods, providing a tranquil retreat. Stone tiles create a pathway leading to the tub, which is nestled amongst ferns and other foliage, enhancing the natural setting.

Home in Mill Valley

Redwood Treehouse, Downtown Mill Valley

4.99 out of 5 average rating, 134 reviews

A wooden deck features two lounge chairs facing the ocean, providing unobstructed views of the sun setting over the Pacific. The surrounding native garden enhances the tranquil atmosphere, while rolling coastal bluffs can be seen in the background.

Home in Bolinas

Beach House ~180° Views, Hot Tub, Curated Interior

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

4.94 out of 5 average rating, 440 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

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, 124 reviews

Private Cottage near Redwood City and San Carlos Downtowns

4.92 out of 5 average rating, 165 reviews

Home in Montara

Entire Private Coastal Retreat - Spectacular Ocean

4.96 out of 5 average rating, 183 reviews

The exterior of a multi-level home features a blend of large windows and a distinctive round window. The light-colored facade is complemented by lush greenery and flowering plants in the foreground. A spacious front deck is visible, enhancing the inviting appearance of the property.

Home in Burlingame

SFO Panoramic Views 4BR/3BA near SF-Silicon Valley

Family- and pet-friendly home rentals

4.81 out of 5 average rating, 144 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

4.95 out of 5 average rating, 111 reviews

The living room features a light-filled space with large windows on either side, framed by minimalist decor. A modern fireplace serves as a focal point, complemented by a surfboard mounted above. Comfortable seating is arranged around a neutral-toned coffee table on a textured area rug.

Home in Half Moon Bay

Seaside Home Modern Retreat with Breathtaking

4.93 out of 5 average rating, 452 reviews

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

Caboose in the redwoods just outside of Cupertino

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, 307 reviews

Serene Modern Home with Yard & Parking

4.93 out of 5 average rating, 175 reviews

An aerial view captures the expansive outdoor area of the Anton Menlo Apartments. A resort-style pool is centrally located, surrounded by lounge chairs and shaded seating areas. Lush landscaping and modern architecture define the space, with additional amenities visible, including a community lounge.

Apartment in Menlo Park

Beautiful Spacious Living w/Resort Like Feel

4.98 out of 5 average rating, 395 reviews

A serene outdoor scene captures a tent nestled among trees, with rustic wooden chairs positioned nearby. In the background, rolling vineyards extend towards the horizon, with hills visible under a clear sky, inviting guests to enjoy the natural surroundings.

Yurt in Los Gatos

Yurt in Vineyard Overlooking Monterey Bay

4.94 out of 5 average rating, 157 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, 212 reviews

Charming Studio

Family-friendly home rentals with a pool

4.95 out of 5 average rating, 103 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

4.91 out of 5 average rating, 116 reviews

A two-story home is surrounded by well-maintained grass and trees. The front features a welcoming porch with two green chairs, a brick chimney, and large windows showcasing the indoor space. A pathway leads to the entrance, framed by manicured landscaping.

Home in Palo Alto

Large Home in Palo Alto, 5 bedrooms, Pool

4.99 out of 5 average rating, 364 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

4.97 out of 5 average rating, 1,020 reviews

An outdoor area features a serene pool surrounded by blooming flowers and lush greenery. The distant horizon showcases a sparkling view of the city lights below, under a clear evening sky transitioning from dusk to night.

Guesthouse in Los Gatos

Cabana in Sierra Azul Open Space Preserve

4.94 out of 5 average rating, 153 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

4.92 out of 5 average rating, 174 reviews

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

3 BR Home on Vineyard nr Palo Alto & Stanford

Guest suite in Walnut Creek

The bedroom features a spacious bed with neutral bedding accompanied by vibrant accent pillows. A colorful piece of wall art adds visual interest, while two windows allow natural light to filter in. A small sitting area is present with a plant nearby, enhancing the welcoming feel.

5 out of 5 average rating, 611 reviews

Garden Oasis Studio with Spa and Pool Walnut Creek