Family-friendly holiday rentals in Milpitas

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, 167 reviews

Airstream With Gorgeous Views of Silicon Valley

Stay in a Vintage Airstream with Scenic Views Near San Jose, CA Escape to our beautifully restored vintage Airstream, perfectly located in the peaceful San Jose foothills. Just minutes from the heart of Silicon Valley, our hillside retreat offers stunning panoramic views, cozy charm, and easy access to top Bay Area attractions. Only 12 minutes from Highway 680, you're ideally situated to explore San Francisco, Santa Cruz, Napa Valley, and beyond — all while enjoying a quiet, nature-filled stay.

Indoor spacesKitchenCheck-in

4.97 out of 5 average rating, 156 reviews

A spacious living room is illuminated by soft LED lighting along the walls. A comfortable white sofa faces a mounted television, while a red side table adds a pop of color. The open layout leads to a kitchen visible in the background.

Home in East San Jose

1 bedroom 1 bath house w/parking

This stylish private home is perfect for visiting and working close to downtown San Jose . There is large living room and a kitchen. There is pool table and workout area in the garage. Beautiful ambience LED lights in the living room and Game/ GYM Room. Centrally Located close to San Jose downtown , Tech companies (Silicon Valley), Levi's Stadium, Concert Arenas, San Jose State University, San Jose Airport, Amusement Parks, Many late night taco stands that you can walk to. Tesla EV Charging.

Indoor spacesKitchenComfort

Guest suite in East San Jose

The guest suite features a spacious layout with a large bed and a futon sofa bed. A television is positioned against the wall, and a mini refrigerator is accessible. Light-colored walls and natural wood flooring enhance the inviting atmosphere. A doorway leads to the adjacent private bathroom.

4.87 out of 5 average rating, 207 reviews

Cozy Suite, Private Entrance + Bath (Pets Welcome)

★ Private Guest Suite ★ Separate entry w/keypad ★ Private Parking ★ Self check-in/check-out available ★ En-suite Private Bathroom ★ High Speed Wi-fi ★ Please ask about pets first! (add $20-30/night per pet. See details below) ★ Amenities ★ Central San Jose. Close to Highway 101/680/280 Freeway ★ 13 mins drive to SJ airport ★ 3-5 mins walk to VTA/Bus Stop ★ Shopping & dining options nearby《You’ll love it because of the relaxing ambiance, complete privacy, clean bed, coziness, & convenience

FamilyIndoor spacesComfort

Home in Downtown San Jose

4.9 out of 5 average rating, 100 reviews

Bright, Stylish Suite in Central Silicon Valley

Newly remodeled guest suite, only steps away from SJSU. The main house hosts a boutique architect firm, adding creative energy by day while evenings stay quiet. This retreat offers modern comforts in a prime Silicon Valley location. With quick access to I-280, Hwy 87, and Hwy 101, you’re minutes from Caltrain, SJC Airport, the Convention Center, SAP Center, Levi’s Stadium, and downtown San Jose. Ideal for business or leisure, the suite blends style and convenience for a comfortable stay.

KitchenIndoor spacesComfort

4.94 out of 5 average rating, 156 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.

KitchenIndoor spacesDecor

4.99 out of 5 average rating, 156 reviews

Home in Santa Clara

The most charming and private guesthouse.

Centrally located modern guesthouse in Santa Clara. About 10 min drive to Apple Park, Nvidia HQ, Lawrence Caltrain Station, 49ers Levis stadium, Santa Clara Convention Center, Valley Fair Mall/Santana Row, SAP Center/Downtown SJ, SJ Mineta Airport. Your suite will have its own big gourmet Kitchen, specious full bathroom, queen bed with spacious walk in closet, Wi-Fi, TV, desk, and backyard with an outdoor seating area. There is also a shared washer and dryer in the back of the house.

Indoor spacesFamilyShared spaces

4.78 out of 5 average rating, 148 reviews

A paved area is framed by lush greenery and banana plants, providing a serene outdoor space. The white exterior of the building contrasts with the vibrant plants, while a gravel pathway leads to the entrance, inviting a peaceful atmosphere.

Guest suite in Berryessa

Banana Tree Lodge Private Entry 1b/1b Guest Suite

"The Banana Tree Lodge is a furnished 1bed/1bath in-law suite with a separate entrance, 500 sq. ft, located near San Jose Air Port. Unit has Wi-Fi, microwave, refrigerator, kitchen sink. The lodge has free neighborhood street parking, and a shared backyard. This quite neighborhood has running and biking trails and easy access to 101/680 N/S. Parties and events are not allowed. smoking is not allowed within the house premises. 7 Days or more has discount.

KitchenIndoor spacesShared spaces

5.0 out of 5 average rating, 107 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.

KitchenIndoor spacesQuiet

Guesthouse in Downtown San Jose

An outdoor patio area is shown beneath a wooden pergola adorned with warm string lights, creating a cozy ambiance at night. A large 65-inch TV is mounted on the wall, while comfortable dining and lounging furniture is arranged for relaxation and socializing.

4.99 out of 5 average rating, 141 reviews

Near Japantown & SJC ARPT, King Bed, Fast Internet

Our detached guesthouse near Japantown & DTSJ is designed for comfort and relaxation. Enjoy a king-sized ultra-comfy bed, A/C in both the bedroom and living room/kitchen, a fully equipped kitchen, in-unit washer and dryer, and a dedicated workstation with an ergonomic sit-stand desk. The private outdoor pergola space features a 65” Smart TV, ambient lighting, ceiling fan, propane fire pit, and dining/lounge area. Free and ample street parking included.

KitchenIndoor spacesDecor

4.82 out of 5 average rating, 783 reviews

A private studio space features a queen-size bed with crisp white linens. A comfortable gray sofa sits beside a glass coffee table. Artwork depicting local themes adorns the walls, complemented by a ceiling fan and ample natural light from nearby windows.

Apartment in Berryessa

Silicon Valley Studio Apartment

Enjoy your privacy in this private studio apartment with private entrance. No need to interact with anyone -- not even the host. This studio apartment has a completely private heating and air conditioning system. Newly remodeled with 24 new wall outlets - including 6 USB wall outlets, a new furnace, new bathroom fixtures, and new security lighting. It features a queen-size Sleep Number Bed, air conditioning, and guaranteed driveway parking.

Indoor spacesFamilyHeating

Guesthouse in Downtown San Jose

Large glass doors open to reveal a bright, open kitchen and living area. A modern design includes white cabinetry, stainless steel appliances, and a comfortable seating area with a light sofa. Natural light floods the space from a skylight above.

4.99 out of 5 average rating, 231 reviews

Quiet guesthouse near SJ airport with EV charger

Kick back and relax in this calm, stylish space. Brand new guesthouse build and landscape completed in 2023. Our guesthouse offers a full kitchen, WiFi, self check-in, FREE parking and washer and dryer. Tesla Universal EV charger Level 2 60 amp avilable for guest use. Centrally located in Downtown San Jose. A quick drive to the SJ airport, SAP Center, San Pedro Square, Levi’s Stadium, San Jose State University and Santa Clara University.

KitchenFamilyWalkability

Guesthouse in Downtown San Jose

The open living space features a contemporary kitchen equipped with stainless steel appliances, including a refrigerator and oven. A dining table for four is positioned centrally, surrounded by sleek chairs. Light wood flooring enhances the bright atmosphere of the area, complemented by white cabinetry and a decorative sliding barn door.

4.98 out of 5 average rating, 639 reviews

Private Cottage nearby Airport/SAP/SJ Downtown/SCU

The cottage is located in the central of Silicon Valley. Convenient access to most attractions and places. About 7 to 15 minutes drive from most attractions: San Jose Airport, SAP Center, Avaya Stadium, San Jose Downtown, Caltrain/Diridon Station, Levi Stadium, SJ state university, Santa Clara university, Malls. Santa Cruz 35 minutes, San Francisco airport- 45 minutes. Close to major freeways I-280, I-880, US-101.

KitchenFamilyNearby

Popular amenities for Milpitas family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 157 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

KitchenIndoor spacesParking

4.94 out of 5 average rating, 354 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.

Condo in Santa Clara

The Alpaca House

Indoor spacesKitchenLaundry

4.98 out of 5 average rating, 133 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

KitchenFamilyValue

4.8 out of 5 average rating, 290 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

KitchenIndoor spacesCheckout

Guesthouse 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.

4.97 out of 5 average rating, 644 reviews

Cabana with Warm Watsu Pool

Indoor spacesKitchenSolo travel

Guest suite in Willow Glen

4.95 out of 5 average rating, 204 reviews

Private Queen Suite-Pool & Hot Tub, private entry

Indoor spacesFamilyView

4.94 out of 5 average rating, 447 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

Indoor spacesFamilyLaundry

4.99 out of 5 average rating, 618 reviews

The spacious interior features rustic wooden walls and exposed beams. A cozy bed with plush bedding is highlighted by warm lighting. A comfortable seating area is nearby, along with a large round mirror and a modern flat-screen TV on the wall.

Guesthouse in Los Gatos

Sanctuary in Sierra Azul Open Space Preserve

Indoor spacesKitchenNearby

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 221 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 spacesKitchenBackyard

4.93 out of 5 average rating, 216 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

KitchenFamilyCheckout

Guesthouse in Willow Glen

The exterior of the studio is framed by a stone facade, featuring large glass doors that open to reveal a cozy interior. Plush seating and a dining table are visible inside, with the gourmet kitchen in the background. Natural light brightens the space, enhanced by the greenery outside.

4.99 out of 5 average rating, 229 reviews

TheStudio in Willow Glen (San Jose) CA-95125

FamilyKitchenSleep quality

4.98 out of 5 average rating, 408 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

Indoor spacesKitchenPets

4.96 out of 5 average rating, 475 reviews

The entrance to the studio cottage is framed by lush greenery, with steps leading up to an open door. Natural light spills into the interior, showcasing wooden accents and inviting outdoor space. Paved stones create a pathway, bordered by a wooden fence.

Guesthouse in Sunnyvale

Private cottage in a garden

FamilyIndoor spacesLayout

4.93 out of 5 average rating, 454 reviews

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.

Home in San Jose

Comfortable Whole Home on two house lot

Indoor spacesFamilyGetting around

4.93 out of 5 average rating, 459 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

FamilyIndoor spacesBiking

5.0 out of 5 average rating, 118 reviews

A glimpse into the living space is provided, showcasing a bright area with wooden floors and a dining table surrounded by chairs. A shower stall can be seen through an open door, adding to the cottage's functionality. A mirror hangs near the entrance, enhancing the welcoming feel.

Guesthouse in Livermore

Quiet wine country cottage sleeps 4 - Pet Friendly

FamilyIndoor spacesAccess

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 255 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

KitchenFamilyComfort

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, 296 reviews

Apartment above Levi Stadium.

FamilyIndoor spacesHiking

4.96 out of 5 average rating, 103 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 spacesFamilyAmenities

4.99 out of 5 average rating, 374 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

FamilyKitchenDecor

Place to stay in Los Gatos

An aerial view displays the serene property nestled among towering redwoods. A sparkling pool is surrounded by lush greenery, with a patio and seating area visible in the background. The landscape features diverse plants, enhancing the tranquil atmosphere of this private retreat.

4.8 out of 5 average rating, 108 reviews

Stay Alpha Home • Modern Redwood Retreat with Pool

Indoor spacesFamilyParking

4.92 out of 5 average rating, 150 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

FamilyIndoor spacesBarbecue

4.93 out of 5 average rating, 178 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 spacesKitchenCheckout