Holiday houses in Cupertino

Santana Row Loft | Luxe Stay in Silicon Valley

Amazing Loft with the View at Santana Row The Space 1,090 sq ft open-concept loft on the top floor with soaring ceilings, minimalist décor, and stunning views of Santana Row. 2 bed / 1.5 bath- perfect for couples, families, or business travelers. INCLUDED ∙King-size bed with premium Ghost mattress + full-size bed ∙NEST thermostat ∙Small library for light reading ∙New fridge and TV Access & Parking: Keyless entry +1 designated underground parking spot. Accessible via garage or lobby with key fob.

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.

Bright Luxury 4B3B House/family/business nr Apple!

Beautiful renovated 4B3B SFH. Cozy house with transitional design, Great location and safe neighborhood, Quick access to De Anza Blvd, Highway 85, and I-280, Walkable to restaurants and groceries. Easy Self check-in with Smart locks, 3 Queen size beds, 1 twin size bed & 1 storage bed, Comfortable home for up to 8 guests and 4 cars, 65 Inches Roku LED TV, High-speed Wifi, Large Master bedroom w/ private entrance in the backyard, Security Smart House, Sunny and relax backyard.

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!

Modern 2BR/1BA with Large Patio and Pool Table

Escape to your Silicon Valley sanctuary! This stunning 2nd-floor retreat boasts 2 spacious bedrooms, a modern bathroom with premium fixtures, and a 600 sq ft private balcony ideal for relaxation. Enjoy endless entertainment with a professional-grade pool table. Located minutes from top tech hubs, shops, supermarkets, and restaurants, this home offers the perfect balance of work and play—combining comfort, style, and convenience for an elevated lifestyle. On site EV charging.

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.

Your private and cozy 2BR home away from home

Comfortable apartment in a peaceful residential neighborhood at the heart of Silicon Valley. The space feels like home with a private entrance, modern amenities, stainless steel appliances, washer & dryer, and other creature comforts. Walkable and bike-friendly neighborhood with a large park nearby. Perfect for a work trip, family visit, or vacation getaway. Super-hosted by Danielle & Jay.