Family-friendly holiday rentals in San Jose

4.99 out of 5 average rating, 125 reviews

Apartment 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.

Indoor spacesFamilyParking

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.

KitchenFamilyBreakfast

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.

4.96 out of 5 average rating, 178 reviews

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.

FamilyKitchenGrill

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.

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!

FamilyIndoor spacesParking

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.

FamilyIndoor spacesAccuracy

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.

Indoor spacesKitchenNearby

4.99 out of 5 average rating, 111 reviews

A spacious living area features light wooden flooring and neutral-colored walls. Plush seating includes a comfortable loveseat and a recliner. A dark coffee table rests in the center, while natural light enters through the windows, illuminating the open space that connects to the dining area and kitchen.

Home in Berryessa

Urban 4BR Oasis: Your Home Away

Escape to our unique 4BR oasis! A fusion of modern design and family comfort awaits. Unwind in spacious living areas – a cozy family room for bonding, a chic living room for relaxation. Serene bedrooms and well-appointed bathrooms cater to groups. Our tranquil backyard, a private haven for all. A fully-equipped kitchen for culinary adventures, Wi-Fi for work/play, and a workspace for convenience. Nestled in a peaceful neighborhood, close to attractions, it's the best of both worlds.

FamilyKitchenSleep quality

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!

KitchenFamilyCheck-in

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.

FamilyKitchenOutdoor spaces

The exterior of a charming blue bungalow is presented, featuring a well-maintained landscape with lavender plants and a shaded tree. A red brick chimney adds character to the home, alongside a private driveway and a wooden fence surrounding the yard.

4.85 out of 5 average rating, 137 reviews

Spacious 3BR/2BA | Near SJC & Convention Ctr

Welcome to our charming 3BR classic bungalow with a private backyard, covered patio, outdoor sofa, and dining for four. Enjoy blazing-fast WiFi 6, in-unit washer/dryer, and dedicated parking. Centrally located in Silicon Valley with quick access to I-280, Hwy 87, and 101. Less than 10 minutes to SJC Airport, Caltrain, downtown San Jose, SAP Center, Levi’s Stadium & more. Whether for work or play, we’re here to make your stay smooth and comfortable—reach out anytime!

FamilyKitchenDecor

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.

Indoor spacesFamilyLaundry

A spacious living area features a comfortable gray sectional sofa paired with a wooden coffee table, set atop a soft area rug. Natural light fills the room through large windows, and wooden beams accentuate the ceiling. An inviting fireplace and decorative plants enhance the atmosphere.

4.91 out of 5 average rating, 151 reviews

Newly Built, Luxury Living

Located just four blocks from the famous “San Jose’s local treasure” downtown Willow Glen, you are surrounded by historic homes, unique architecture, tree-lined streets, and a thriving community. We want you to have a stress-free experience, so there is no check-out to-do list. Just enjoy your stay and leave 👍 You are in the front main home. No parking on the driveway, but there’s plenty of free street parking right in front of the house.

KitchenIndoor spacesCleanliness

Popular amenities for San Jose family-friendly rentals

Kitchen

Wifi

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.

Paradise Treehouse & Heavenly Cabin

Indoor spacesKitchenDecor

4.99 out of 5 average rating, 159 reviews

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

FamilyKitchenNearby

4.95 out of 5 average rating, 183 reviews

Charming Willow Glen Home with Spacious Yard

Indoor spacesFamilyAmenities

Guest house in Willow Glen

A tranquil Watsu pool is surrounded by lush greenery and vibrant plants. A fabric shade cover is suspended overhead, providing protection from the sun. Natural stone flooring complements the pool's serene ambiance, creating a peaceful retreat atmosphere.

Cabana with Warm Watsu Pool

KitchenIndoor spacesWifi

4.97 out of 5 average rating, 651 reviews

Guest suite in Willow Glen

Private Queen Suite-Pool & Hot Tub, private entry

KitchenIndoor spacesBack garden

4.95 out of 5 average rating, 218 reviews

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

KitchenIndoor spacesOutdoor spaces

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

Indoor spacesFamilyLayout

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

Indoor spacesKitchenShared spaces

Family- and pet-friendly home rentals

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 spacesKitchenAccess

4.96 out of 5 average rating, 253 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

Indoor spacesFamilyLocation

4.93 out of 5 average rating, 226 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

FamilyIndoor spacesLocation

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

FamilyIndoor spacesHospitality

A cozy living area features a light blue sofa and a stylish lounge chair, complemented by a decorative area rug. Wall art is displayed above a low table, while houseplants adorn the space. Warm, orange accent walls provide a welcoming touch.

4.93 out of 5 average rating, 298 reviews

Convenient 1BR Home Near SJ Airport & Santa Clara

FamilyKitchenBreakfast

Camper van/Motorhome 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.

Airstream With Gorgeous Views of Silicon Valley

Indoor spacesFamilyComfort

4.98 out of 5 average rating, 175 reviews

Guest house 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.

MolivuHomes 2BR: KingBed, PrivateYard, PetFriendly

KitchenIndoor spacesPets

4.98 out of 5 average rating, 112 reviews

4.92 out of 5 average rating, 235 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

Indoor spacesFamilyLaundry

Family-friendly home rentals with a pool

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

KitchenFamilyGetting around

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

KitchenIndoor spacesLocation

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

Indoor spacesKitchenValue

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 spacesFamilyBreakfast

4.93 out of 5 average rating, 179 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.

Flat in Menlo Park

Beautiful Spacious Living w/Resort Like Feel

FamilyIndoor spacesGetting around

4.87 out of 5 average rating, 196 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!

FamilyIndoor spacesBiking

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.

4.8 out of 5 average rating, 239 reviews

Beautiful Large 4BR Home with POOL

Indoor spacesFamilyAccess