Vacation rentals in Cupertino

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Top-rated vacation rentals in Cupertino

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A modern kitchen and dining area is shown, featuring sleek cabinetry and a marble countertop. A round dining table with two chairs is positioned beside a plush gray sofa. Natural light enters through large windows adorned with blinds, illuminating the light wood flooring.
Home in San Jose
4.86 out of 5 average rating, 184 reviews

Modern House near Apple Park

Welcome to your perfect home away from home! This modern, clean, and peaceful 2-bedroom, 1-bathroom unit features cozy queen-size beds, ideal for a restful stay. Located in an upscale neighborhood, it’s just a 5-minute drive to Apple HQ and shopping centers and a 7-minute walk to supermarkets and a variety of international restaurants. The spacious unit includes a stylish family room, a modern kitchen, and a contemporary bathroom, designed for your comfort and enjoyment.(San Jose/Cupertino area)

Guest favorite
A cozy guestroom features a spacious bed covered with a vibrant teal bedspread. A white kitchenette is visible, equipped with essential appliances, while a small dining area is present nearby. Natural light filters through sheer curtains, illuminating the modern decor.
Guesthouse in Santa Clara
4.93 out of 5 average rating, 163 reviews

Entire guesthouse Santa Clara smart lock entrance.

New remodeled clean and cozy guesthouse in a prime location of Silicon Valley. You will be close to everything when you stay here. Minutes drive to the best Bay Area shopping and dining experiences Santana row and Westfield Valley Fair. Nividia 7min. drive, Apple Park 11 min. drive, Google headquarters Mountain View 15min. Sap center, Levi’s Stadium, and Great America are all nearby. Walk to shops, restaurants and Target shopping center. A close 10 minute drive to San Jose International Airport.

Top guest favorite
A spacious living area is highlighted by a comfortable sofa adorned with decorative pillows. The open kitchen is visible, featuring modern appliances and a dining table. Large windows allow natural light to fill the room, enhancing the airy atmosphere.
Guesthouse in Santa Clara
4.94 out of 5 average rating, 105 reviews

Santa Clara Guest House w/King Bed and Parking

Newly updated guest house centrally located in the Silicon Valley. Easy access to everything! Close to San Jose Int. Airport, Downtown San Jose, Santa Row, Valley Fair Shopping Center, and more! This stylish guest house will meet all your needs. Fully equipped kitchen with refrigerator, oven/stove, Keurig coffee pot, and dish essentials. Large bedroom with comfortable King bed, en-suite bathroom, laundry, and lots of closet space. Beautiful private yard and private drive-way parking included!

Guest favorite
The living area features a spacious gray sectional sofa with blue accent pillows, situated adjacent to a wooden coffee table. A patterned rug adds texture to the light wood flooring. Natural light fills the room from the window, which opens to the backyard.
Home in Cupertino
4.95 out of 5 average rating, 310 reviews

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. **www.accesscupertino.com** for 3d tour of interior and videos. 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

Top guest favorite
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.
Guesthouse in Cupertino
4.94 out of 5 average rating, 101 reviews

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.

Top guest favorite
A colorful tiny home is seen surrounded by tall redwood trees. The exterior showcases vibrant blue and yellow walls, contrasted by natural wood planters filled with greenery. Sunlight filters through the trees, enhancing the inviting outdoor space.
Tiny home in Boulder Creek
4.96 out of 5 average rating, 199 reviews

Custom Cabin Retreat in the Redwoods

This retreat offers guests a unique experience of living in a well designed, minimalist space while having all one really needs. From the nautically-inspired curved ceiling w/ skylights to the custom redwood trim, this cozy retreat will inspire. Relax on the private deck with the fire pit, walk to the river or enjoy the local trails thru the towering redwoods. Santa Cruz beaches are just 35 min away, 25 min to Big Basin and Henry Cowell, and 35 min to fine dining in Saratoga.

Top guest favorite
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
4.94 out of 5 average rating, 404 reviews

Silicon Valley Work Retreat | Wellness Oasis

PLEASE CONTACT US FOR SUN–THU DISCOUNTS (2+ NIGHTS). Peaceful upscale 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve with private trail access. Ideal for business travelers, couples, and nature lovers. Fast fiber Wi-Fi, dedicated workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, heated saline pool May–Oct. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Guest favorite
A spacious sleeping area features a queen bed with a light, textured blanket and a padded headboard. Subtle pendant lighting hangs above, complementing the large artwork and indoor plant on a wall-mounted shelf. Natural light filters through a nearby window.
Guest suite in Sunnyvale
4.97 out of 5 average rating, 117 reviews

Private Entrance and Walking to Apple Park

Nicely remodeled designer private studio unit. High speed internet 1200 Mbps and 4K Roku-enabled TV Separate external key-code entrance. Separate heating and air conditioning control, handheld remote. Desk area. Spotless attached bathroom. Cathedral wooden ceiling. Super comfortable queen bed, comforter, padded headboard. Zoned, dimmable lighting. Small kitchenette area with counter, microwave, refrigerator, sink, utensils. Friendly, responsive hosts.

Top guest favorite
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.
Guesthouse in Downtown San Jose
4.99 out of 5 average rating, 143 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.

Top guest favorite
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
4.93 out of 5 average rating, 433 reviews

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.

Top guest favorite
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.
Guest suite in San Jose
4.94 out of 5 average rating, 661 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

Top guest favorite
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
4.94 out of 5 average rating, 287 reviews

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.

Popular amenities for Cupertino places to stay

When is the best time to visit Cupertino?

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Frequently Asked Questions

  • Do apartment rentals in Cupertino have free parking?

    Absolutely! We offer over 60 apartment rentals with free parking in Cupertino. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Townhouse Rentals in Cupertino?

    Enhance your stay in our Townhouse Rentals with the most popular amenities: over 20 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Where should I stay in Cupertino?

    Make yourself at home in Cupertino by choosing from our most frequently booked neighborhoods. We have over 590 vacation rentals in Brookview, over 520 vacation rentals in Monta Vista, and over 590 vacation rentals in Blue Hills.

  • Are there vacation rentals with a dedicated workspace in Cupertino?

    Yes! Work meets play with ease at over 250 vacation rentals in Cupertino featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in hotel rentals in Cupertino?

    Experience the best of Cupertino with our hotel rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Cupertino have a kitchen?

    Absolutely! We offer over 90 apartment rentals with a kitchen in Cupertino. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Cupertino have wifi?

    Absolutely! We offer over 10 hotel rentals with wifi in Cupertino. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Cupertino have air conditioning?

    Absolutely! We offer over 10 guesthouse rentals with air conditioning in Cupertino. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Cupertino?

    Four-legged friends are welcome in Cupertino. Choose from more than 100 vacation rentals for guests traveling with pets.

  • Are there Cupertino vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 110 vacation homes with pools in Cupertino, available on Airbnb. Make a splash and soak up the sun in style!

Quick stats about vacation rentals in Cupertino

  • Total vacation rentals

    Explore 440 vacation rentals in Cupertino

  • Nightly prices starting at

    Cupertino vacation rentals start at € 26 per night before taxes and fees

  • Verified guest reviews

    Over 12,460 verified reviews to help you choose

  • Family-friendly vacation rentals

    130 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 100 rentals that welcome pets

  • Vacation rentals with a pool

    110 properties feature pools

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

  • Wi-Fi availability

    440 of Cupertino vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cupertino rentals

  • 4.8 Average rating

    Cupertino stays are highly rated by guests—averaging 4.8 out of 5!