Family-friendly holiday rentals in San Jose

4.99 out of 5 average rating, 124 reviews

Condo in San Jose

New! Stylish Condo on Santana Row

Enjoy an indulgent experience at this stylish and centrally-located condo in the heart of Santana Row. "The Row" is a premium blend of residential, retail, and dining spaces in the center of Silicon Valley. Revel in gourmet restaurants, upscale shops, cinemas and a lively atmosphere with outdoor concerts and seasonal festivals. Take a short stroll to Westfield Valley Fair to continue your journey in fine dining, entertainment and shopping venues Located right off of highways 17, 280, and 880.

4.94 out of 5 average rating, 529 reviews

An open living area features a glass dining table surrounded by modern chairs. Natural light pours in through expansive windows, illuminating the airy space. A staircase with wooden steps and metal railing leads to the upper floor, while decorative accents enhance the contemporary design.

Loft in San Jose

Santana Row Luxury Executive 2 Story Loft

Beautiful, luxury and clean 2 story open plan loft on the top floor at Margo building right on Santana Row. 2 bedroom 1,5 bath. Panoramic view of the mountains, downtown San Jose and the planes landing at SJC. Your favorite restaurants and shops downstairs. Valley Fair Mall is across the street. Brand new king size bed in the Master Bedroom, walk-in closet, kitchen, Nespresso coffee, teas. Underground parking with EV/Tesla hookup. Security on site 24/7. Ideal for business travelers and families.

Home in Downtown San Jose

The open-concept living area features a spacious, L-shaped sectional sofa adorned with colorful cushions. A stylish coffee table occupies the center, while the kitchen and dining spaces are visible in the background. Abundant natural light is provided by large windows overlooking the outdoor area.

4.89 out of 5 average rating, 344 reviews

4Br/3BaHeartDtownSJGemCraftsmanFireplaceSAPAriport

No Party, event This uniquely designed modern Craftsman home is in the heart of downtown SJ &features two units: front & rear.The rear unit offers 4 bedrooms, 3 full bathrooms&1,400 sq ft of stylish living space. Every bedroom includes a TV for your comfort.Guests have full access to the backyard,with a patio set, fruit trees, driveway carport for 2 cars. Conveniently, located near shops, markets, CityHall, museums, SAP Center,airport&major companies like eBay, Adobe, Netflix, Intel, Apple,SJSU.

Home in Downtown San Jose

4.97 out of 5 average rating, 633 reviews

Charming Home nearby Airport/San Jose Downtown/SAP

Centrally located to explore the heart of Silicon Valley. This beautiful home has all the conveniences and is a ideal location to experience all of activities. About 7 to 15 minutes drive from most attractions: SJC airport,SAP center,SJ downtown,Hi-tech companies, Santana Row,Valley Fair Mall, Levi’s stadium,Avaya stadiums,Rose Garden, Great mall outlets,Museums and Restaurants..Santa Cruz 35 minutes. Stanford 25 minutes. San Francisco 45 minutes. Close to major freeways I-280, I- 880, US-101.

4.95 out of 5 average rating, 177 reviews

A spacious and inviting living area is defined by a large sectional sofa and a glass coffee table atop a soft area rug. Natural light floods the space through sliding glass doors that lead to the outdoor deck, enhancing the open concept layout.

Home in Willow Glen

Airy Open Concept Modern Home: 3br/2bath + Office

Newly renovated home with a 1 Master Bedroom Suite, 2 Bedrooms and an Office (1,500 SF). The house features an open concept Kitchen/Dining/Living room with a sliding door to a large deck. The house has been completely decluttered to give you an airy and a peaceful stay. Located just 15 minutes from SJC airport and a short drive to most key destinations in the South Bay Area. Ideal for families or business travelers looking for a home away from home with all the amenities and complete privacy.

Apartment in East San Jose

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.

4.98 out of 5 average rating, 305 reviews

Apartment above Levi Stadium.

18 miles from Levi Stadium! Your Superbowl HQ Take tram to stadium and avoid traffic JAM and parking nightmare! This 2 bedroom apartment. With with spectacular view of Silicon Valley and Levi Stadium). There are two bedrooms, one bathroom and a combined full kitchen/living room. Living room has couch, TV, and Roku streaming. Apartment has good WiFi. Sit on the private deck and you may see wild turkeys, deer, and even a cow! The Rental fee includes the Santa Clara Short Term Rental Tax!

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

Stay on a farm animal rescue in a 38’ yellow school bus conversion. If you are interested we also host an Airbnb Experience called Life With Farm Animals At Rancho Roben Rescues where you get a 90-120 minute up close encounter with all of the animals - taking time to learn about each of the unique creatures that lives here and the opportunity to interact with them directly. Pet a chicken, groom a pony, feed a goat, take a walk patrolling the fields with our livestock guardian dogs.

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!

Enjoy the Bay Area in your own private, quaint, and comfortable cozy home! Gaze out of your master bedroom window or living room to green grass and Bamboo tree lined backyard with fruit trees and 6' fences. The home is in a safe, quiet, neighborhood, within 2-3 minute drive to Oakridge mall. Conveniently located w/all shopping imaginable within 5 minutes drive. Our inviting full kitchen contains pots, pans, dishes, a Keurig coffee maker, rice cooker, Ninja Air fryer and much more.

4.91 out of 5 average rating, 107 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

Welcome to your next unforgettable stay — where comfort meets adventure in a space designed for fun-loving families and couples. 🌟 🧗‍♂️ Sleeping lofts accessed by indoor ladders — best suited for physically agile, adventurous guests 🌳 Relax in a magical backyard featuring a real treehouse, firepit & BBQ 🛁 Unwind in a spa-style bathroom with luxe touches 👨‍🍳 Cook like home in a fully stocked kitchen 🎮 Enjoy games, 65” TVs, and flexible workspaces 🌟 Discover More Below!

A modern kitchen features an island with two wooden bar stools. Bright lighting illuminates the cabinetry, stainless steel appliances, and the marble countertop. A small workspace is situated adjacent to the kitchen, with a step stool available for convenience.

4.91 out of 5 average rating, 151 reviews

Family friendly 5BR house w/backyard +playground

✔No check-out chores ✔High-speed WiFi ✔ Two dedicated workstations ✔ Great amenities for families with children+ Backyard playground ✔ Wood burning fire place Premium furnished single-story home with spacious backyard overlooking Martial Cottle Park with views of Lick Observatory & surrounding hills with nothing to block views. Huge extended family room. Fully furnished large backyard with table, sofas, chairs, kid's play zone & fruit trees. Wifi throughout the house.

4.99 out of 5 average rating, 115 reviews

A modern living area is showcased, featuring a teal sofa, a wooden coffee table, and a television mounted on the wall. Light-colored walls reflect ample illumination from recessed lighting, while a framed mountain artwork adds a subtle touch of décor. A door leads to the outside.

Guesthouse in Berryessa

Private Modern Spacious 1B1B 2 beds|Prime Location

Welcome to your stunning new 1-bedroom, 1-bathroom modern getaway, where style meets practicality. Enjoy cooking a warm meal using the new, fully equipped kitchen. Unwind in the stylish bathroom with premium finishes, or kick back in the living room on the cozy sofa bed, enjoying your favorite shows on the 55-inch smart TV. This beautifully designed home offers a seamless blend of comfort and style, making it ideal for relaxation, work, or exploration.

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

Retreat above the city in this one-of-a-kind home and gaze at the sweeping view of Silicon Valley. Rancho Ruby is a revived 1950s ranch designed with a modern California style. Every amenity and detail has been thoughtfully considered for the tech-savvy travelers. The home is open, peaceful, and cool. It sits on a hilltop, situated on a secluded & gated third acre lot to allow tranquility for guests but is only a 15 minutes drive to the city center.

Popular amenities for San Jose family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 159 reviews

Paradise Treehouse & Heavenly Cabin

4.95 out of 5 average rating, 183 reviews

Home in Willow Glen

Charming Willow Glen Home with Spacious Yard

4.92 out of 5 average rating, 217 reviews

A serene cabin is elevated among trees, connected by wooden stairs to a spacious deck. The deck features seating arrangements and is surrounded by lush greenery, allowing for privacy and a tranquil outdoor experience.

Home in Scotts Valley

Creekside Log Cabin

Home in Downtown San Jose

A spacious living room features two red tufted sofas set against a light grey wall. A patterned blue area rug anchors the seating arrangement, complemented by a coffee table with a decorative centerpiece. Natural light filters through a window, highlighting the room's modern artwork and greenery.

4.95 out of 5 average rating, 173 reviews

NewLuxHome!PoolTable!HotTub!Heart of Downtown SJ

4.8 out of 5 average rating, 295 reviews

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

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.

Guesthouse in Woodside

A beautiful Tree house -your own retreat

Guest suite in Willow Glen

4.95 out of 5 average rating, 217 reviews

Private Queen Suite-Pool & Hot Tub, private entry

4.93 out of 5 average rating, 182 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

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 225 reviews

The spacious kitchen features an expansive island with four bar stools, allowing for casual dining. Light wood flooring complements the bright cabinetry and stainless-steel appliances. A view of the open living area is visible in the background, promoting a welcoming atmosphere.

Home in Santa Clara

4B/2.5B / Office Space / Open Plan / Huge Backyard

4.86 out of 5 average rating, 140 reviews

Cozy 2BR Bungalow | Garden Vibes in Downtown SJ

An open-concept kitchen and dining area is displayed, featuring dark cabinetry and new stainless steel appliances. A dining table with wooden chairs sits adjacent to a spacious island. Soft lighting from pendant fixtures complements the natural light flowing through large windows.

4.93 out of 5 average rating, 459 reviews

Comfortable Whole Home on two house lot

4.92 out of 5 average rating, 234 reviews

A modern living area features a blue sofa adorned with white pillows. A glass coffee table sits on a patterned rug, with decorative items placed thoughtfully atop. An accent chair with a cozy cushion offers additional seating, while framed artwork decorates the walls.

Home in Santa Clara

Executive Class Stay in Tech Hub 3b2B Near SJC

Guesthouse in South San Jose

A contemporary living area is depicted, featuring light-colored furniture and a flat-screen TV mounted on the wall. A round coffee table with a decorative item is placed in front of two sofas. A dining area with curved chairs complements the space, all illuminated by natural light.

4.98 out of 5 average rating, 112 reviews

MolivuHomes 2BR: KingBed, PrivateYard, PetFriendly

Campervan/RV in East San Jose

A vintage Airstream is positioned on a gravel surface, facing a panoramic view of the landscape below. Potted plants add a touch of greenery next to the entrance. The expansive deck offers a space for outdoor relaxation, surrounded by gentle hills and an open sky.

4.98 out of 5 average rating, 172 reviews

Airstream With Gorgeous Views of Silicon Valley

4.97 out of 5 average rating, 107 reviews

Home in Berryessa

Chef's Kitchen + Patio | EV Charger | Near Tech HQ

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, 105 reviews

Modern Cozy House | near Santa Clara | Mini Golf

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 257 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.

Guesthouse in Sunnyvale

Lush Luxury Villa•Sunny Deck & Private Escape•Pool

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

A welcoming exterior view of the family house is showcased, surrounded by a spacious front yard. A large pine tree offers shade while a decorative pot with greenery adds a touch of nature. The driveway leads to a double garage with a clean facade.

4.78 out of 5 average rating, 132 reviews

Modern Rustic Home With Private Pool

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, 158 reviews

Private Oasis with Pool and Fire Pit

4.8 out of 5 average rating, 239 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

4.87 out of 5 average rating, 195 reviews

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!

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