Vacation rentals in Cupertino

New Guest House - Modern Stylish & Central

Silicon Valley life at its best! A newly built spacious guest unit (studio 400+ sqft), 11' extra high ceiling, private entrance, dazzling kitchen, new appliances, 55" 4K TV, washer/dryer, spa-like bathroom, double vanity, high-tech-toilet, hardwood floor, softener treated water, 100% organic cotton linens. Single-family neighborhood is quiet, safe and convenient, close to Apple Park (1.6 miles), Valley Fair/Santana Row(2.2 miles), Kaiser/Valley Med/O'Conner hospitals, easy access to freeway.

Quiet Cozy 3B/3BA in a Prime Location in Cupertino

Experience refined living in this elegant home, perfectly situated in a prestigious and secure neighborhood in Cupertino. Featuring two grand living rooms designed for relaxation and entertainment, this residence offers both space and sophistication. Surrounded by upscale homes and gracious neighbors, you’ll enjoy serene privacy while remaining minutes from fine dining, shopping, and city conveniences. ~2 mins to Safeway and Trader Joe’s ~5 mins to Apple HQ ~10 mins to Vallyfair Mall

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.

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.

M&J @ Spacious SFH 4B2.5B nr Apple/Shpping | 20777

~ The stunning residence welcomes you with a grand entrance boasting a 15 ft high dome ceiling. ~ Spacious open floor plan. ~ High-speed WI-FI up to 400 Mbps, WFH friendly. ~ Fully equipped kitchen. ~ Plenty of parking spaces. ~ Top neighborhood in Cupertino. ~ Great Location, within walking distance to the Apple campus, De Anza College, Cupertino library, City Hall, numerous restaurants, Whole Foods, Chinese/Japanese/Indian grocery stores, a Target store, and pharmacy stores.

Charming Guesthouse by Apple Park

Welcome to your peaceful Silicon Valley retreat! This private guesthouse has a separate entrance, 1 cozy bedroom, and 1 full bath — offering comfort, privacy, and a true home-away-from-home experience. Located in a quiet, safe neighborhood minutes from Apple Park and near Kaiser Permanente, you’ll enjoy easy access to tech campuses, restaurants, and parks while relaxing in a calm residential setting. Perfect for business travelers, couples, or anyone visiting Silicon Valley!

Sunwoods Mtn. House

Escape to Sunwoods Mountain House, a historic 1000 sq ft. cabin gut-renovated into a unique wellness sanctuary in the California coastal redwoods. Just 10 mins to Los Gatos & 20 mins to Santa Cruz. Unwind in the traditional sauna, spa shower, or on the wrap-around deck with fire-pit. Features a full kitchen and dining area as well as a dedicated WFH space with high-speed WiFi. The perfect basecamp for cycling, dining, wine tasting, hiking, Silicon Valley & Santa Cruz.

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.

New Cosy Guesthouse +Private Entrance, Own Parking

New guesthouse with 1 bedroom, full kitchen, stylish bathroom, in-unit washer/dryer. Equipped with new AC, smart TV, fast Wifi, dining table, workspace. Parking on driveway. Private entrance. Central location in West San Jose. Safe neighborhood. 2 minutes walk to groceries. 5 minutes drive to Main Street Cupertino. Near Apple Park, Santa Clara Kaiser, Santana Row with easy access to parks, shopping, dining and major tech companies.

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. 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

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.

Lush Luxury Villa•Sunny Deck & Private Escape•Pool

Romantic private retreat with sunny deck & lush greenery Indoor/outdoor living, vaulted ceilings, garden views Gourmet kitchen, gas fireplace, walk-in shower Aroma & sound therapy Nest-controlled A/C & heat (no shared ducts) Air filtration + eco-friendly cleaning Self check-in/out, fast WiFi Ideal for couples, solo travelers & business trips We welcome families with children aged 8 and older.