Family-friendly holiday rentals in Milpitas

Campervan/Motorhome in 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, 144 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.

Guest house 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.

5 out of 5 average rating, 101 reviews

Near Japantown & SJC ARPT, King Bed, Fast Internet

Our detached guesthouse is centrally located in DTSJ near Japantown, features a king-sized, ultra-comfortable bed and cold mini split A/C system in the bedroom that guarantees a restful night's sleep. A fully equipped kitchen for chefs and for those who need to work during their stay, an automatic ergonomic sit-stand desk. The outdoor oasis includes a huge 65 inch Smart TV, ambient lighting, outdoor ceiling fan, propane fire pit, and dining and lounging area. Street parking is free and ample.

4.9 out of 5 average rating, 173 reviews

A spacious backyard area features lush green grass and charming flowers, illuminated by string lights overhead. A gazebo with outdoor seating is visible, surrounded by a neatly maintained garden. The detached cottage appears inviting in the background, evoking a serene setting during twilight.

Guest house in San Jose

*1 Bed Cottage w/Kitchenette + yard

Enjoy this cozy 450sqft cottage centrally located between Campbell & Downtown San Jose, close to Santa Row & Valley Fair Mall. This studio will meet your needs for an enjoyable stay in a great area. Kitchenette fully equipped with refrigerator, toaster-oven, electric cook-top, coffee maker & dish essentials. Bedroom w/ spacious closet. Comfortable Full size bed, sofa bed for additional sleeping, an a flat screen tv. Netflix and other streaming networks availablel-log in w/your credentials.

A sleek kitchenette is featured with stainless steel appliances, including a refrigerator. A small dining table with two chairs is positioned beside it. A flat-screen TV is mounted on the wall, while a coffee station is visible. A sliding barn door leads to an adjacent area.

4.86 out of 5 average rating, 264 reviews

Modern Studio - SAP SJC Airport Downtown San Jose

Private studio that was designed with function and form. This listing is close by to freeways, SAP center, San Jose Mineta Airport, restaurants, and grocery stores. Your home away from home comes with fully controllable AC and Heater which you can enjoy while watching your favorite show or movie. Whether you are here to work, or just looking for a place to sleep, you'll have the convenience of an office desk, memory foam bed , and a couch/futon. Don't forget about our raindrop shower head!

4.88 out of 5 average rating, 147 reviews

Home in San Jose

Spacious 4bd/3ba w 2 living rooms, 2 XL bedrooms

Welcome to our home, featuring a spacious open floor plan and a patio perfect for outdoor grilling, socializing and relaxation. Located in a peaceful neighborhood in Berryessa district of San Jose, our home is convenient to shopping, dining, public transportation (BART and VTA), and major highways. Private car or use of car share is recommended. This is a perfect house for multi-generational family group travel or work teams opting for a home with kitchen instead of staying in a hotel.

Guest house in Downtown San Jose

A comfortable seating area features a plush gray sofa adorned with green and white accent pillows. A light-colored armchair with a leaf pattern is positioned nearby. Two abstract artworks hang on the wall, complementing a round wooden coffee table topped with lavender in a textured vase.

5 out of 5 average rating, 123 reviews

Pristine Modern Guesthouse w/ Full Kitchen-1B/1B

Enjoy and relax at this stylish experience in this centrally-located 1bed/1bath brand new guesthouse. This newly built home offers all amenities in their pristine condition. Walk to Japantown, SJSU campus, City Hall, short drive from SJC, Coleman shopping center, HWY 87, 101, 280, 880, SAP Center, Convention Center, heart of downtown. Fully stocked european kitchen, free street parking, designer bathroom, Fiber internet and Wi-Fi , work desk, monitor and much more

4.86 out of 5 average rating, 121 reviews

A broad street is depicted, featuring well-maintained sidewalks lined with palm trees. A trash bin is positioned on the curb, and a variety of parked vehicles can be seen. Residential buildings and greenery are visible in the background, under a clear blue sky.

Guest house in San Jose

Entire Private Studio Apt + Kitchen & Backyard

This unit is ideal for couple, family with up to 2 young children. open to long term. Your family will have a place to yourself with big yard right outside your dining/kitchen combo area. With fast internet from AT&T Fiber for your streaming, futon. You'll be close to everything when you stay at this nice centrally located place near Evergreen area, public parks, Raging Water, fast access to restaurants, supermarkets, schools, shopping, public transportation.

A solid-wood queen-size bed is dressed in a navy blue coverlet, featuring plush pillows. A Hello Kitty plush toy adorns the bed, complemented by a decorative striped pillow. The room is illuminated by warm light, enhancing the cozy ambiance.

4.96 out of 5 average rating, 199 reviews

San Jose studio with laundry

This elegant, cozy studio is built with private entrance. It features with a solid wood queen-size bed, private bathroom, TV, private washer/dryer, private patio and reserved driveway parking for our guest. This studio is close to San Jose airport, Downtown, Levi’s Stadium, SJSU, Stanford, Valley Fair and Silicon Valley offices. It is also close to major freeways, 101, 680 and 880, very convenient for working in Silicon Valley and perfect for a relaxing getaway!

4.94 out of 5 average rating, 227 reviews

A studio space features sloped ceilings with natural light from skylights. A full-sized bed is dressed in patterned linens, accompanied by a 43-inch smart TV on a low wooden console. A single armchair with an ottoman is positioned near a dark dresser.

Guest house in Hensley

Private Entrance Studio with in-unit bathroom

Private entrance studio with in-unit bathroom and wet bar, it is located near downtown San Jose and Japantown. 2 min walk to the light rail station (japantown ayer green/blue lines), great for someone traveling or on a business trip. Few minutes drive to Target, Trader Joe, grocery stores, San Pedro Square. This studio unit is converted from the attic of detached garage structure with excellent privacy (1st floor is used as storage) *street parking only*

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.

4.78 out of 5 average rating, 134 reviews

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.

Guest house in Downtown San Jose

A modern living area is depicted, featuring large windows that allow natural light to fill the space. An inviting sofa and a coffee table are positioned in front of a wall-mounted television. The open kitchen showcases sleek cabinetry and a dining table with white chairs.

4.99 out of 5 average rating, 136 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.

A bright sleeping area features a spacious bed with white bedding and a decorative throw. Two bedside lamps illuminate the room, while colorful animal artwork adorns the wall above. A cozy sofa and a small side table complete the inviting atmosphere.

4.94 out of 5 average rating, 654 reviews

Walk to Santana Row + Valley Fair | 6min drive SJC

Private guest suite with it's own front door, bedroom and bathroom. There is no kitchen but we provide a mini fridge, microwave and kettle. It is a short walk to Santana row and Valley Fair Mall and a 5 minute drive to SJC Airport. This suite is 1 of 2 Airbnbs on the property. 1 Parking spot on the driveway, directly in front of the Airbnb. 0.3 mi to Santana Row 0.3 mi to Westfield/Valley Fair 3.1 mi to SJC Airport

Popular amenities for Milpitas family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 275 reviews

A tranquil pool surrounded by a spacious deck features lounge chairs for relaxation. The sun casts a warm glow over the water, highlighting the adjacent charming cottage and lush greenery. Tall trees provide shade, enhancing the serene atmosphere.

Guest house in Oakland

Pool, Jacuzzi, Sauna, Huge Views, gated, ADU

4.91 out of 5 average rating, 367 reviews

The image depicts a serene garden pathway leading to two adjacent cabins, framed by vibrant greenery and flowering plants. A wooden trellis is visible, providing shelter, while soft lighting from the cabins enhances the calm atmosphere. A mixture of stone and mulch surfaces directs attention toward the entrance.

Guest house in Oakland

Guesthouse Garden Retreat

4.96 out of 5 average rating, 173 reviews

The image features a clear pool surrounded by a stone edge, with vibrant orange and purple flowers in bloom along the perimeter. Lush green palm trees and other landscaping elements provide a natural backdrop, creating a serene outdoor setting.

Guest suite in Cambrian

Private Queen Suite-Pool & Hot Tub, private entry

4.95 out of 5 average rating, 994 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

Guest house in San Leandro

The exterior of the recently renovated garden unit displays a soft green facade with a welcoming white entrance door. Decorative windows are positioned above the door, enhancing natural light. A wooden deck leads to the entrance, framed by lush vegetation and a bicycle is parked nearby.

4.96 out of 5 average rating, 294 reviews

Garden getaway near SF

Apartment in Rivermark of Santa Clara

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.

4.94 out of 5 average rating, 332 reviews

The Alpaca House

4.91 out of 5 average rating, 166 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

4.79 out of 5 average rating, 272 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

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 163 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

4.93 out of 5 average rating, 345 reviews

The guesthouse entrance is framed by a neatly landscaped area, featuring a spacious path made of stone tiles leading to the front door. Elegant wrought iron railings and manicured greenery enhance the inviting setting under clear blue skies.

Guest house in Evergreen

Evergreen Valley Hillside retreat

4.95 out of 5 average rating, 460 reviews

The interior of the cabin features a single bed dressed in a blue and white plaid coverlet alongside two soft pillows. A kitchenette area with wooden cabinets and a small fridge is visible, complemented by a round mirror and decorative wall art of a forest scene.

Guest house in La Honda

Bicycle Shack @ La Honda Pottery

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.

4.85 out of 5 average rating, 179 reviews

Cozy Suite, Private Entrance + Bath (Pets Welcome)

4.93 out of 5 average rating, 431 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

4.96 out of 5 average rating, 425 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

4.96 out of 5 average rating, 313 reviews

Tall redwood trees rise from the forest floor, creating a serene canopy. A distant view of the bay is visible through the trees, with a blanket of clouds resting over the landscape. The sky is clear, contrasting with the lush greenery of the forest.

Guest house in Woodside

SkyHigh Redwoods Retreat with Bay Views

4.92 out of 5 average rating, 265 reviews

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.

Home in San Jose

Convenient 1BR Home Near SJ Airport & Santa Clara

Family-friendly home rentals with a pool

Apartment in Civic Center

A modern living space presents a deep-seated couch paired with a stylish coffee table, set against a backdrop of vibrant artwork. Natural light filters in through a window, while a door leads to the outside. A dining area is visible in the corner.

4.91 out of 5 average rating, 304 reviews

Lakeside Retreat (w/ private parking)

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, 446 reviews

Quiet Poolside Cottage for Solitude

4.92 out of 5 average rating, 168 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 !

4.93 out of 5 average rating, 150 reviews

Cottage in Ben Lomond

Central Coast; Meadow, Hot Tub, Polite Pets Welcom

4.94 out of 5 average rating, 163 reviews

A resort-style pool surrounded by lounge chairs is visible, with modern apartment buildings framing the scene. The area is bright and airy, showcasing a leisure space ideal for relaxation, with neatly landscaped greenery along the pool's edge.

Flat in Menlo Park

Charming 2BR Apartment near tech Giants & Stanford

4.89 out of 5 average rating, 463 reviews

A spacious bed with an intricate patterned cover is positioned in a well-lit room. Towels are neatly arranged on the bed. A colorful piece of wall art adds a touch of character, while natural light filters through a nearby window.

Guest suite in Woodside

Separate entry room near Stanford

4.99 out of 5 average rating, 344 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