Family-friendly holiday rentals in Cupertino

4.96 out of 5 average rating, 101 reviews

A spacious master bedroom features a king-size bed with a light-colored blanket, complemented by a bench at the foot. A comfortable armchair is situated nearby, and a large window allows natural light to illuminate the room. A ceiling fan and hardwood flooring add to the spacious feel.

Guest suite in Sunnyvale

Bright Guest Suite in the Heart of Silicon Valley!

If you travel for business or just visiting beautiful California for vacation, you will love this absolutely new gorgeous unit, located within 15 minutes, from Apple, other major Silicon Valley companies, and San Jose Airport! Everything was meticulously selected thinking about our guests convenience and enjoyment, from new furniture and bedding, to organic toiletries and desk with a printer. And if you stay longer, you will appreciate a washer and dryer in the unit so that you could pack light.

KitchenIndoor spacesParking

Guest suite in Santa Clara

A spacious guest room features a four-poster bed dressed in soft, white linens. Large arched windows provide natural light, adorned with sheer curtains. A cozy seating area with a cushioned chair and decorative throw offers additional comfort, creating a relaxing environment.

New Guest House - Modern Stylish & Central

Silicon Valley life at its best! A newly built spacious guest unit (studio 400+ sqft), 11' extra high ceiling, private entrance, dazzling kitchen, new appliances, 55" 4K TV, washer/dryer, spa-like bathroom, double vanity, high-tech-toilet, hardwood floor, softener treated water, 100% organic cotton linens. Single-family neighborhood is quiet, safe and convenient, close to Apple Park (1.6 miles), Valley Fair/Santana Row(2.2 miles), Kaiser/Valley Med/O'Conner hospitals, easy access to freeway.

Indoor spacesFamilyLayout

4.89 out of 5 average rating, 169 reviews

4.93 out of 5 average rating, 134 reviews

A spacious yard features a children's play structure with a slide and swings, accompanied by a patio seating area under a shade umbrella. Lush green grass enhances the outdoor setting, surrounded by wooden fencing for privacy.

Guest house in Sunnyvale

Sunnyvale2B/1B/Family/Free EV Charging/AC/WiFi/PKG

~Close to many tech companies ~Yard with kids play structure/Gazebo ~Pack'n Play for baby ~Free parking and EV Charging ~Hi-speed WiFi ~New kitchen and appliances ~Sofa bed for 1 extra person ~Central AC and Heater with Nest ~Smart 55''TV with Netflix. ~Walking distance to downtown/shops/parks ~Quick access to 101 fwy and Central Expy ~Kitchen equipped with utensil essentials ~Best value Airbnb The big lot is separated into 2 units. This Unit B is a 2B/1B ADU with full privacy, the RED area

KitchenFamilyParking

4.95 out of 5 average rating, 110 reviews

The bedroom features a spacious bed with neutral-toned bedding, accompanied by a desk and a comfortable chair. A wall-mounted TV and a standing heater are visible. Natural light is allowed in through the window, dressed with sheer curtains, creating a calm environment.

Guest house in Cupertino

Guesthouse with kitchen,bath and laundry

Private guesthouse/ in-law unit in Cupertino, walking distance from major tech companies with Private entry Convenient access to new restaurants and nightlife. Short commute to freeway and airport. High speed independent internet /Ethernet connection. Comcast streamingTV box, also uverse tv. Airconditioning vent in the bedroom. Wall heater. Portable fans and heater . It includes kitchen, dinette and full bath. It has shared laundry and shared backyard. Nice, quiet neighborhood.

FamilyKitchenCondition

The living room features a sleek black sleeper sofa adorned with geometric patterned pillows and a rich red throw. A wooden tray sits atop a gray blanket, and a floor lamp provides soft lighting. A wall art piece depicting a beach scene adds a serene feel to the space.

5.0 out of 5 average rating, 169 reviews

High end home in Silicon Valley, Non-Smokers only

This is a 1 BR/1 BA fully furnished attached house with its own paved private entry way, completely separate from the main house. This is the perfect home away from home while you are relocating, on extended assignment, or on vacation in Silicon Valley. Located in a highly desirable West San Jose residential neighborhood but within 5-minute walking distance to Westgate Mall, Grocery stores, Restaurants, Eateries and Movie Theaters. Street parking available in front of the house.

Indoor spacesKitchenHospitality

An open-plan living area features a light-colored sectional couch and a wooden coffee table adorned with decorative items. A well-lit kitchen area includes modern appliances and a spacious dining table, creating a welcoming space for gathering and relaxation.

4.88 out of 5 average rating, 206 reviews

Bright Luxury 4B3B House/family/business nr Apple!

Beautiful renovated 4B3B SFH. Cozy house with transitional design, Great location and safe neighborhood, Quick access to De Anza Blvd, Highway 85, and I-280, Walkable to restaurants and groceries. Easy Self check-in with Smart locks, 3 Queen size beds, 1 twin size bed & 1 storage bed, Comfortable home for up to 8 guests and 4 cars, 65 Inches Roku LED TV, High-speed Wifi, Large Master bedroom w/ private entrance in the backyard, Security Smart House, Sunny and relax backyard.

Indoor spacesFamilyDecor

4.94 out of 5 average rating, 468 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

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.

Indoor spacesFamilyHot tub

4.96 out of 5 average rating, 344 reviews

Home in Cupertino

Newly rebuilt ultra clean designer home

Newly renovated ultra clean designer home in duplex minutes from Apple campus. Highly walkable, the entire home has been recently rebuilt from the studs with new top of the line designer furnishings, kitchen essentials, appliances, and toiletries. Disney+, Hulu, Cable TV, and Nespresso coffee included during stay with ultra-fast internet up to 500mbps. 5 min to Whole Foods 12 min to Apple Park 20 min to Stanford

Indoor spacesKitchenWifi

4.94 out of 5 average rating, 320 reviews

The kitchen features wooden cabinetry and stainless steel appliances, with a central island and barstool seating. Natural light floods in through sliding glass doors that lead to a lush outdoor area. A round wooden dining table is set with a small vase containing a flower.

Home in Cupertino

2BR House + Patio + Office near Apple and Main St.

Spacious 2BR + private office in a quiet, walkable neighborhood. 600+ Mbps fiber Wi-Fi, two private parking spots, and a fully stocked kitchen. Just a 3-minute walk to 6 restaurants, 7-minute walk to Cupertino Main Street, and 2-minute drive to Hwy 280 and Lawrence Expressway. Includes two queen beds, smart TVs with streaming, and a backyard garden patio. Perfect for remote work or a comfortable Bay Area stay.

FamilyIndoor spacesParks

4.99 out of 5 average rating, 258 reviews

A dining area features a round table surrounded by four white chairs, illuminated by a decorative chandelier. Natural light enters through large windows adorned with sheer curtains, complementing the light green walls and adding a bright, open feel to the space.

Guest house in Sunnyvale

Lush Luxury Villa•Sunny Deck & Private Escape•Pool

Romantic private retreat with sunny deck & lush greenery Indoor/outdoor living, vaulted ceilings, garden views Gourmet kitchen, gas fireplace, walk-in shower Aroma & sound therapy Nest-controlled A/C & heat (no shared ducts) Air filtration + eco-friendly cleaning Self check-in/out, fast WiFi Ideal for couples, solo travelers & business trips We welcome families with children aged 8 and older.

FamilyKitchenValue

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.

4.92 out of 5 average rating, 159 reviews

Private Oasis with Pool and Fire Pit

Escape to our private oasis where every detail is designed for your ultimate comfort. Indulge in a refreshing swim in our pool. Unwind and relax in our outdoor lounge area complete with a cozy firepit, perfect for savoring a glass of wine with your loved ones. Whether it’s a family retreat, a couples getaway or a work gathering, your ideal stay begins here! ** We do not offer pool heating **

Indoor spacesKitchenTV

4.92 out of 5 average rating, 134 reviews

The exterior of the master suite is showcased, featuring a pathway leading to a glass door. Vibrant yellow flowers and greenery frame the entrance, while a tree provides shade. The space is surrounded by a gravel yard and clear blue skies.

Guest suite in Sunnyvale

Spacious Business Suite with Serene Backyard View

A master suite with private entrance is within walking distance to Apple Park and Cupertino Main Street. It is located in a quiet Sunnyvale neighborhood and near groceries, and many vibrant restaurants. It features a high speed 1.2G Wifi and split ductless AC. Mountain View corporate commuting bus is nearby. Ample parking space. Everything you need for a successful Silicon Valley visit.

Indoor spacesKitchenNearby

Popular amenities for Cupertino family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 183 reviews

Home in Willow Glen

Charming Willow Glen Home with Spacious Yard

KitchenIndoor spacesAccess

Superhost

A California bungalow style home is presented with a welcoming yellow exterior. A well-maintained front yard features manicured grass and shrubs. A concrete driveway extends to the gated entrance. Two inviting seating areas are positioned near the front porch, enhancing the property's curb appeal.

Bungalow in San Jose

Cozy 2BR Bungalow with Hot Tub near Santana Row

KitchenIndoor spacesHot tub

4.8 out of 5 average rating, 295 reviews

4.94 out of 5 average rating, 455 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

FamilyKitchenBathroom

4.93 out of 5 average rating, 183 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

KitchenIndoor spacesGetting around

4.94 out of 5 average rating, 221 reviews

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.

Guest house in Woodside

A beautiful Tree house -your own retreat

FamilyIndoor spacesOutdoor spaces

Guest suite in Willow Glen

Private Queen Suite-Pool & Hot Tub, private entry

Indoor spacesKitchenCondition

4.95 out of 5 average rating, 219 reviews

4.94 out of 5 average rating, 357 reviews

A bright bedroom is equipped with a spacious bed and two bedside tables, each featuring a lamp. Colorful botanical wall art adds detail to the decor. A full-length mirror stands against the wall, with light filtering in through a window fitted with vertical blinds.

Apartment in Santa Clara

The Alpaca House

FamilyIndoor spacesLaundry

4.94 out of 5 average rating, 165 reviews

A modern living area features a comfortable blue leather sofa and a light, textured armchair. A wooden coffee table with decorative items is centered on a patterned rug. Large sliding glass doors provide a view of the sunset and access to the outdoor space.

Home in East San Jose

Views for Miles | Hot Tub | Gated Hilltop Home

FamilyKitchenWifi

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 157 reviews

A serene bedroom is highlighted by a spacious bed with a padded headboard and soft bedding. Natural light pours in through sliding glass doors, revealing a private outdoor area. A bedside table with a lamp complements a white dresser against the wall.

Home in Santa Clara

M&J@Gorgeous remodeled 3B2B SFH/Bay Area | 2944

Indoor spacesFamilyCheckout

4.91 out of 5 average rating, 215 reviews

The modern exterior of the house features a combination of wood and light-colored siding. A covered porch is highlighted by vertical lighting, while large windows provide views of the surrounding landscape. A manicured lawn and driveway contribute to the welcoming entryway.

Home in Mountain View

Upscale Modern House Near Mountain View Downtown

FamilyKitchenDecor

4.91 out of 5 average rating, 109 reviews

An enchanting treehouse is nestled among the branches, adorned with warm string lights against a twilight sky. Adjacent, a living area features a large smart TV mounted on the wall above an electric fireplace, creating a cozy focal point.

Tiny home in San Jose

Family Favorite: Mickey Dream Loft & TREE house

Indoor spacesKitchenDecor

A spacious backyard is surrounded by a wooden fence and features a well-maintained mini golf area, highlighted by soft string lights above. The area is illuminated by evening light, enhancing the inviting atmosphere, with a clean concrete pathway leading to the green.

4.96 out of 5 average rating, 106 reviews

Modern Cozy House | near Santa Clara | Mini Golf

FamilyIndoor spacesQuiet

4.96 out of 5 average rating, 461 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

Indoor spacesFamilyBack garden

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.

4.92 out of 5 average rating, 243 reviews

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

KitchenIndoor spacesCondition

4.94 out of 5 average rating, 187 reviews

The living area is organized around a dark wood coffee table and features a blue sofa with yellow accent pillows. A vibrant orange accent wall complements a mounted smart TV. A small desk is situated nearby, alongside a colorful patterned chair.

Flat in Sunnyvale

🌟Cheerful 2B2B in prime location 🌲Redwood Pl Apt 3

KitchenFamilyLaundry

4.95 out of 5 average rating, 296 reviews

A bright living area features a cream-colored sofa adorned with gray cushions, overlooking a wooden coffee table. A flat-screen TV is mounted on a metallic stand, complemented by decorative plants and shelving units against the wall. Natural light filters in through sheer curtains.

Home in Santa Clara

Peace, eat & sleep in your private cozy cottage

FamilyIndoor spacesCondition

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 104 reviews

The solar-heated pool is illuminated at night, showcasing a serene blue hue. Three water features flow gracefully into the pool, highlighting the tranquil setting. The surrounding area is dimly lit, enhancing the peaceful ambiance of the outdoor space.

Home in Campbell

Luxury 4-Suite Carbon-Neutral Home With Pool

Indoor spacesFamilyQuiet

4.88 out of 5 average rating, 125 reviews

A light blue exterior of the cottage is complemented by white double doors and a large window. Floral arrangements in red planters and a white bench enhance the inviting entrance. A comfortable chair adds to the cozy outdoor seating area.

Guest house in Sunnyvale

Private & Quiet Garden Cottage

FamilyIndoor spacesAccess

4.92 out of 5 average rating, 100 reviews

A spacious living area is designed with a large L-shaped sectional sofa adorned with colorful throw pillows. A dark coffee table is centrally placed on a vibrant area rug, while natural light filters through large windows, enhancing the overall brightness of the room.

Home in Santa Clara

Silicon Valley Executive home in Santa Clara

Indoor spacesKitchenHospitality

Superhost

A spacious living area is equipped with a flat-screen TV mounted on the wall and an ornate cabinet. A comfortable grey chair and a glass coffee table are positioned on a soft carpet. Natural light is welcomed through a nearby window, enhancing the cozy atmosphere.

Home in Mountain View

Little Poolside House near Downtown. New AC!

KitchenFamilyBack garden

4.87 out of 5 average rating, 196 reviews

4.94 out of 5 average rating, 160 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

Indoor spacesFamilyPool

4.98 out of 5 average rating, 305 reviews

A refreshing pool glistens under the sun, surrounded by well-manicured green lawns. A white picket fence encloses the area, enhancing the garden's appeal. The charming two-story structure features a sloped roof and multiple balconies, providing a welcoming atmosphere in a serene outdoor setting.

Flat in East San Jose

Apartment above Levi Stadium.

FamilyIndoor spacesAccess