Family-friendly holiday rentals in Los Gatos

4.97 out of 5 average rating, 159 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

4.99 out of 5 average rating, 1,021 reviews

A charming green guesthouse is nestled among towering redwood trees. The structure features multiple windows that bring in natural light, enhancing the connection with the surrounding forest. Sunlight filters through the branches, creating a serene outdoor atmosphere.

Cabin in Los Gatos

Private Guest-House in the Redwoods

Our custom built guesthouse was completed in 2016. It is situated on 5 redwood-covered acres, 10 minutes south of Los Gatos and 20 minutes from Santa Cruz. We have easy access to hiking and biking trails, world-class wine-tasting, microbreweries, shops, amazing dining, and more! There is something for everyone in our area! We are surrounded by a 35 acre tree farm, so it's very private, yet close to the silicon valley! Our property has a standby generator so we are not affected by power outages.

A light blue cottage is set amidst lush greenery and towering trees. The exterior features multiple windows, offering views of the surrounding landscape. A narrow pathway leads to the inviting front door, framed by flowering plants, enhancing the tranquil setting.

4.97 out of 5 average rating, 124 reviews

Mountain Retreat

Escape to the serene beauty of the Santa Cruz Mountains of Los Gatos! Our charming cottage rental is nestled amidst the towering redwoods, 30mins from Silicon Valley or Santa Cruz, and only 15mins from downtown LG, but feels isolated if you want get away from it all. The cottage features a living room (w/optional murphy bed) & full kitchen/dining area. Amenities like wifi, streaming and washing/dryer available in unit. Bedroom features king size bed and private backyard area. Pet friendly.

Guest house in Monte Sereno

The cottage exterior features a charming design with a slate stone patio and a round dining table with two chairs. Glass double doors provide access, and large windows offer views of the surrounding greenery. The roof is intricately shaped, complementing the natural setting.

4.98 out of 5 average rating, 457 reviews

Quiet Poolside Cottage for Solitude

New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

4.8 out of 5 average rating, 132 reviews

A bright living area features light wooden flooring and white walls. Two rattan chairs are arranged around a small table in front of a decorative fireplace, while a modern TV sits on a console nearby. Natural light streams through two sets of double doors leading outside.

Guest suite in Los Gatos

Bright Garden Suite in Silicon Valley

This sun-soaked suite has a private entrance and access to a beautiful garden patio, complete with night-time ambiance and a fireplace. The big bay window provides a view into the lush fruit, flower, and vegetable garden right outside. The comfy bed and beautiful old-town neighborhood add to the warm, homey feel. The suite is tucked away from the busiest parts of the city, perfect for a hub in the middle of NorCal's best attractions: SF, Carmel, Pebble Beach, Monterey, Santa Cruz, and more.

The exterior of the townhome is softly illuminated by outdoor lighting, highlighting the welcoming front entrance. A large oak tree provides natural coverage, while lush greenery surrounds the pathway, offering a sense of privacy and tranquility in a serene nighttime setting.

4.95 out of 5 average rating, 102 reviews

Five Star Smart Home Living Experience

SUPER BOWL CLOSE LOCATION!! Nestled beneath a century old oak tree and only a 5-10 minute walk to downtown Los Gatos or Vasona Park sits a newly constructed 900 square foot 1 BR, 1.5 bath loft style luxury townhome with a private front entrance and backyard. This exclusive experience in downtown Los Gatos is ideal for someone (or a couple) looking for the comfort, quiet and privacy of a detached home in the center of one of the San Francisco Bay Area’s most desirable communities.

A private stone patio is adorned with wooden chairs, overlooking a garden filled with plants. The sunset illuminates the sky with soft hues of pink and orange, creating a serene backdrop against the rolling hills and trees.

4.97 out of 5 average rating, 111 reviews

Oak&Bloom cottage - Los Gatos, 2 bedrooms, private

Beautifully remodeled, sparkling clean, and cozy private two-bedroom cottage with sweeping canyon and mountain views, located less than 2 miles from charming Downtown Los Gatos. Enjoy mornings with Nespresso coffee in the peaceful private yard, explore nearby parks, and access scenic hiking and biking trails just minutes away. Inside, the cottage offers a fully equipped kitchen, air conditioning in every room, and fast fiber internet. Santa Cruz Beach is a scenic 30-minute drive.

Guest house in Almaden Valley

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.

4.97 out of 5 average rating, 1,016 reviews

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

Guest house in Monte Sereno

A vibrant garden is showcased, featuring blooming red flowers and lush green plants. A stone patio leads to a tranquil blue pool, framed by greenery and distant hills. Decorative pottery is placed among the flora, adding charm to the natural setting.

4.91 out of 5 average rating, 232 reviews

Greenwood Guest House, a Peaceful Oasis

Welcome to Greenwood Guest House, a 1 bedroom, 1 bath private house situated in a peaceful and expansive backyard with a pool, tennis court, and beautiful scenery. Our space is a good fit for business trips, couple vacations, and family visits. The kitchenette and laundry room make longer stays quite enjoyable. Easy access to Highway 17 and 85, 15 minute drive to San Jose airport (SJC) and 2 minute drives to either downtown Los Gatos or Saratoga.

4.84 out of 5 average rating, 256 reviews

A round dining table is set for four, featuring red placemats and white dinnerware. Glasses are positioned beside each plate, and stylish utensils are arranged on either side. The wooden chairs are designed with a light finish, complementing the warm tones of the table.

Guest suite in Los Gatos

Mountain Gem - $1M VIEW

We are offering a 1-bedroom apartment on the lower level of a 2-unit house. It is located in a very beautiful place and has a huge balcony with a million-dollar view of the Santa Cruz mountains. Close by 17 highway, which can take you to Los Gatos in 10 minutes, and Santa Cruz - in 20. Great for Bay Area business travelers. Ideal for Santa Cruz beach vacationers. 15 minutes to gorgeous nearby wineries. Got everything one needs for a super stay.

4.87 out of 5 average rating, 142 reviews

A cozy sleeping area features a queen bed adorned with a patterned duvet cover. Natural light filters through a large window framed by curtains, illuminating a decorative wall piece nearby. A bedside lamp rests on a side table, complementing the minimalist design.

Guest suite in Los Gatos

Modern studio in charming Los Gatos,Silicon Valley

It is a guest studio with an independent private entrance in a newly built home in quiet residential neighborhood in Los Gatos, CA. The studio can comfortably host up to 2 adults. The studio is close to Santa Cruz mountains with world class wineries, state parks and beaches. It is also in the heart of Silicon Valley, a few miles away from offices of Netflix, Apple etc. We are 15 mins away from SJC airport and 40 mins from SFO airport.

A cozy living area features two leather sofas positioned around a rustic coffee table. Natural light filters through large windows, illuminating the space. A rocking chair adds a touch of charm beside an accent lamp, and a soft area rug adds warmth to the flooring.

5 out of 5 average rating, 165 reviews

Orchard Cottage in convenient countryside location

Orchard Cottage is a newly refurbished historical home in a rural neighborhood 10 minutes from downtown Los Gatos. Lots of wildlife and beautiful scenery make this location in the Santa Cruz Mountains a peaceful retreat from city life. Enjoy your private deck and yard or visit our ducks for a mini-farm experience. Lots of nearby hiking and wineries, and only 25 minutes to Santa Cruz beaches. Please contact me with any questions!

Popular amenities for Los Gatos family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A modern studio features a spacious bed with light bedding and a decorative pillow reading 'relax'. Built-in cabinets flank the bed, while a stylish chair and a small table are positioned nearby. A woven wall hanging adds texture, and a large mirror reflects the natural light.

4.92 out of 5 average rating, 413 reviews

Los Gatos/Cambrian COTTAGE-HOT TUB/pvt.parking

4.9 out of 5 average rating, 187 reviews

A spacious deck offers a panoramic view of fog-covered hills, with a golden sunset in the background. Multiple seating arrangements, including lounge chairs, are positioned for relaxation. An umbrella provides shade, while a table is set for dining outdoors.

Guest house in Saratoga

Newly Built Studio, 2000 FT Elevation with Jacuzzi

4.95 out of 5 average rating, 173 reviews

A welcoming entrance is framed by mature trees, with a pathway of pavers leading to the front door. Lush green foliage and colorful flowers provide a vibrant touch, complementing the classic white exterior of the home and the dark shutters enhancing the overall charm.

Home in Willow Glen

Charming Willow Glen Home with Spacious Yard

4.94 out of 5 average rating, 437 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

4.98 out of 5 average rating, 116 reviews

A private yard is surrounded by tall trees, featuring a hot tub with bubbles rising to the surface. A hammock is visible to the side of the yard, alongside two Adirondack chairs. The cabin's entrance is shown, with a window allowing natural light to enter.

Cabin in Boulder Creek

Forest Cabin & Hot Tub

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

4.95 out of 5 average rating, 1,035 reviews

A cozy living area features a comfortable gray sofa adorned with patterned cushions. Natural light enters through multiple windows, highlighting a black wood stove. A rocking chair and a small side table add to the inviting setup, complemented by neutral carpeting.

Cottage in Ben Lomond

Sunny redwood forest cottage

4.99 out of 5 average rating, 181 reviews

A cozy living area showcases a wood-burning stove with a warm fire glowing inside. The walls are painted in a calming green hue, accented by rustic decor such as a mounted deer head and circular wall art. A view into another room is visible through French doors.

Cabin in Felton

Redwood cabin retreat + hot tub + dogs ok + creek

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 233 reviews

A single-story home is set against a clear sky, featuring a well-maintained front yard with a variety of blooming flowers and shrubs. Palm trees add a tropical touch, while a paved driveway leads to an attached garage.

Home in San Jose

Gorgeous 3-bedroom home, quiet, close to shopping!

4.96 out of 5 average rating, 113 reviews

A modern workspace is highlighted by a wooden desk and clear chair, accompanied by a lamp. A wall-mounted television displays an ocean scene. A kitchenette with a microwave and mini-fridge is visible, while a bathroom area with a sink and mirrors is seen in the background.

Guest house in San Jose

Luxe Suite with Private Yard & AC

4.96 out of 5 average rating, 245 reviews

A queen-size bed is centered between two light, airy curtains and adorned with a colorful patterned throw blanket. Framed wall art in earthy tones flanks the headboard, while bedside tables house decorative items. Natural light filters in through the window, creating a serene atmosphere.

Bungalow in Milpitas

Casa Blanca - Mediterranean inspired Serene and Minimal Abode

5 out of 5 average rating, 217 reviews

A hot tub is positioned under a wooden gazebo, surrounded by lush greenery and tall trees. A colorful hanging chair is visible nearby, inviting relaxation. The outdoor space features a patterned area rug, and the sound of nature creates a tranquil ambiance.

Cabin in Soquel

Coastal Redwood Cabin | Hot tub | Private Creek

4.98 out of 5 average rating, 125 reviews

A cozy bedroom is presented with a wooden accent wall and large windows on either side, allowing natural light to flood the space. The bed features decorative pillows and a colorful throw blanket, complemented by a small potted plant on the side.

Cabin in Bonny Doon

Eclectic Escape

4.89 out of 5 average rating, 277 reviews

An inviting Victorian-style home features a charming front yard with vibrant greenery and colorful flowers. The entrance is framed by red doors and decorative architecture. A wooden fence with blue pickets lines the property, enhancing the welcoming atmosphere of this historic residence.

Flat in Campbell

Victorian Paradise Downtown Campbell intelliBed

4.96 out of 5 average rating, 440 reviews

The living and dining area features a comfortable sectional sofa arranged around a coffee table, with a dining table for four chairs situated nearby. A wall-mounted television and bright windows allow natural light to enter, while a partially visible bathroom is located to the right.

Guest suite in Campbell

Cottage - bedroom, living, bath and small kitchen

4.99 out of 5 average rating, 341 reviews

The A-frame cabin stands among tall Redwoods, featuring a striking red star above the entrance. Outdoor seating is provided in the form of a white chair on the deck, framed by lush greenery and scenic pathways.

Cabin in Felton

Dreamy cabin in Redwoods +fireplace+tub for 2+dogs

Family-friendly home rentals with a pool

4.91 out of 5 average rating, 192 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 !

4.8 out of 5 average rating, 229 reviews

A spacious living area features a striking stone wall, complemented by a large flat-screen TV mounted above an elegant dark cabinet. Plush seating options, including a brown leather sofa and chairs, invite relaxation, while a decorative chandelier adds a refined touch to the room.

Home in Willow Glen

Beautiful Large 4BR Home with POOL

4.99 out of 5 average rating, 361 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.

Guest house in Woodside

Rustic Cabin in the Redwoods

4.97 out of 5 average rating, 230 reviews

A private swimming pool is surrounded by lounge chairs under shade umbrellas. The pool, featuring a gentle curve, has clear blue water and an entry step. Lush greenery and a fence provide privacy, while distant views of a serene landscape can be seen in the background.

Home in Aptos

Private Pool Villa for family getaways

4.94 out of 5 average rating, 152 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 San Jose

Cozy BUS on Farm Animal Rescue with CITY VIEW

4.98 out of 5 average rating, 118 reviews

The entrance to the Amesti School features a deep red wooden facade with large windows. A pair of inviting chairs are positioned on the covered porch, complemented by a simple light fixture. The front door is framed by an elegant trim, welcoming guests.

Home in Watsonville

Old Amesti Schoolhouse mid-bay amidst farmland

4.91 out of 5 average rating, 136 reviews

A bright living area features a spacious sectional sofa adorned with neutral cushions. A modern coffee table sits in the center, complemented by a decorative bowl. Natural light streams through multiple windows, illuminating the light wooden floor and the cozy fireplace with a stone surround.

Home in San Jose

Private Oasis with Pool and Fire Pit