Holiday houses in Cupertino
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Top-rated holiday rentals in Cupertino
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Santa Cruz A-Frame
This unique A-Frame cabin, in a quiet mountain neighborhood with private creek access, was handbuilt in 1965 and remodeled in the summer of 2024. Now a little slice of heaven on the creek in the redwoods. *5-10 min to Henry Cowell Redwoods State Park, Roaring Camp Railroad, Loch Lomond Recreation Area, the Trout Farm Inn, Quail Hollow Ranch + Felton stores. *20 min to Santa Cruz, beach + Boardwalk. *1 min to Zayante Creek Market (EV charger) Find us on social: Insta @SantaCruzAFrame
3 bed Home-Large backyard +firepit in Santa Clara!
Nestled in the heart of Silicon Valley, this beautifully updated 3-bedroom, 2-bathroom home offers everything you need for a comfortable stay. Perfect for families or groups, this spacious home combines modern amenities with cozy charm, ensuring you feel right at home from the moment you arrive. -Home Gym -Entertainer's Backyard w/fire pit, an outdoor dining table, and propane BBQ -1 King bed, 1 Queen bed, 1 Full bed -Updated Kitchen w/ new appliances -Plenty of Parking -Dedicated Workspace
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 desirable & beautiful 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.
⭐Luxurious Stunning Resort House Silicon Valley⭐
🏡 Welcome to 📸 PortalCourtyard: a serene retreat in the heart of Silicon Valley. Tucked in a quiet neighborhood, this resort-style escape is minutes from Apple campuses and walkable to shops, cafés and bus stations. Perfect for work, exploring, or a restful staycation. ✨ Elegant, peaceful, and rich in character: • 🌿 Asian-themed loft with tatami mat, tea station & 65" TV • 📚 Towering bookcases & hardwood floors • 🔥 Stylish Fire pit & tranquil courtyard • ⚡ 1Gbps internet
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.
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.
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
Boutique 2BR/2BA | Private Garden | Silicon Valley
💛 The Space Welcome to one of San Jose’s most unique Airbnbs — a beautifully designed boutique home with something most Silicon Valley rentals simply don’t have: your own private garden. Whether you’re here for a family vacation, a business trip, a romantic getaway, or a group escape, this 2-bedroom, 2-bathroom home is your perfect base in the heart of Silicon Valley. Sleeps up to 5 guests in comfort and style.
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
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.
BRAND NEW construction home waiting for you
OMG ! BRAND NEW CONSTRUCTION home is waiting for you. it has 10foot high ceiling to double your sense of space. All furniture, appliances, and almost everything are brand new. The property is located in a quiet, safe and beautiful neighborhood, 5 minutes walk to the park, 5 minutes drive to department stores, restaurants, gym and other shopping centers. 10 minutes drive to Apple HQ.
Popular amenities for Cupertino holiday rentals
Other great holiday rentals in Cupertino
SWEET HOME | 3 bedroom w/ fully fenced backyard
Modern & Spacious Guesthouse in Cupertino
💯 Designers’ Paradise in Central Silicon Valley
Newly built stylish guesthouse
Beautiful large private studio w/ garden view
Modern Suite in Cupertino
Spacious Cupertino Home: near Apple HQ & Freeways
Your private and cozy 2BR home away from home
When is the best time to visit Cupertino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $206 NZD | $216 NZD | $211 NZD | $206 NZD | $223 NZD | $220 NZD | $218 NZD | $211 NZD | $206 NZD | $206 NZD | $209 NZD | $207 NZD |
| Avg. temp | 10°C | 12°C | 13°C | 15°C | 17°C | 19°C | 20°C | 20°C | 20°C | 18°C | 13°C | 10°C |
Frequently Asked Questions
What are the best places to stay in Cupertino?
Main Street and surrounding neighborhoods are often suggested for their easy access to food, shopping, and parks. Family-oriented areas near schools and quiet residential streets can be appealing for travelers seeking a relaxed atmosphere.
What are the best things to do in Cupertino with kids?
Families often explore Memorial Park’s playgrounds, discover wildlife at Rancho San Antonio Open Space Preserve, or engage with interactive history at the Cupertino Historical Society & Museum. Local science and art events offer hands-on learning.
What are some of the best things to do in Cupertino?
Explore the Apple headquarters Visitor Center, stroll through Rancho San Antonio Open Space Preserve, and enjoy recreational activities at Memorial Park. Local restaurants, farmers markets, and cultural events add to the city’s inviting mix.
How is the weather in Cupertino?
Cupertino sees mild winters around 42–59°F (6–15°C), with rain most frequent from November to February. Summers are sunny and dry, typically between 56–77°F (13–25°C), so light layers and sun protection are useful in warmer months.
When is the best time to visit Cupertino?
Late spring and early fall are often recommended for visits, with comfortable temperatures and seasonal events like the Cherry Blossom Festival. Summer has dry, sunny weather, while winter brings moderate rain and cooler days.
What are the best places to visit in Cupertino?
Popular spots include the Apple headquarters Visitor Center, Rancho San Antonio Open Space Preserve, and Memorial Park. Art installations, historical sites, and local shopping centers around Main Street showcase Cupertino’s vibrant character.
What are some hiking trails in Cupertino?
Cupertino has hiking trails at Rancho San Antonio Open Space Preserve, where you can observe wildlife and gentle valleys. Fremont Older Open Space Preserve is also frequently suggested for scenic views and moderate trails.
What are some family activities we can do in Cupertino?
Cupertino has playgrounds, green spaces, and interactive exhibits at the Cupertino Historical Society & Museum. Picnics at Memorial Park, hands-on learning in local science centers, and seasonal community events are frequently suggested for family outings.
What are some of the best day trip ideas from Cupertino?
Day trips often include exploring regional parks, visiting cultural attractions in nearby cities, or discovering wineries and coastal areas around Silicon Valley. Urban adventures and nature walks are frequently suggested for a change of scenery.
Are there any pet friendly accommodations available in Cupertino?
Cupertino has pet-friendly stays, especially in residential neighborhoods and around Main Street. Parks in the area often have walking paths suitable for pets, making it easy to explore the city together.
What are some local tips for visiting Cupertino?
Cupertino has both tech-driven attractions and locally rooted eateries, so take time to explore neighborhoods around Main Street and enjoy diverse cuisine. Comfortable walking shoes are helpful for parks, and many green spaces feature shaded picnic areas.
What is Cupertino known for?
Cupertino is often recognized as the home of Apple’s headquarters and its role in Silicon Valley’s technology scene. The city also has extensive parks, welcoming neighborhoods, and diverse dining reflecting local and global cultures.
What are the best hidden gems to explore in Cupertino?
Explore local parks like Rancho San Antonio Open Space Preserve, which is often recommended for nature walks, or discover community spaces such as the Cupertino Historical Society & Museum. Neighborhood bakeries and small cafes around Main Street frequently surprise with unique flavors.
What are the best foods to try in Cupertino?
Cupertino has a mix of Asian cuisines, locally rooted bakeries, and farm-to-table eateries. Dim sum, ramen, and fusion desserts are frequently suggested, with seasonal produce featured in many menus.
What should I bring for a trip to Cupertino?
Pack light layers and comfortable shoes, as weather varies from cool, rainy winters to warm, sunny summers. Sunscreen and a hat are helpful for outdoor activities, and a reusable water bottle is useful when exploring parks.
What is the nightlife in Cupertino like?
Cupertino has a relaxed nightlife scene, with casual bars, contemporary restaurants, and community gathering spots around Main Street. Live music and social events take place at local venues, with a welcoming, laid-back atmosphere.
What are the most popular events or festivals in Cupertino?
The Cherry Blossom Festival in spring and Diwali Festival in autumn are often recommended, celebrating community and cultural traditions. Cupertino also hosts seasonal outdoor concerts and community gatherings at Memorial Park.
Are there family friendly vacation rentals in Cupertino?
Cupertino has a variety of family-friendly vacation rentals, with options near parks and residential neighborhoods. Many properties provide amenities such as spacious living areas, backyards, and easy access to playgrounds.
Quick stats about holiday rentals in Cupertino
Total holiday rentals
Explore 410 holiday rentals in Cupertino
Nightly prices starting at
Cupertino holiday rentals start at $52 NZD per night before taxes and fees
Verified guest reviews
Over 12,570 verified reviews to help you choose
Family-friendly holiday rentals
130 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 100 rentals that welcome pets
Holiday rentals with a pool
110 properties feature pools
Rentals with dedicated workspaces
230 properties have a dedicated workspace
Wi-Fi availability
410 of Cupertino holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Cupertino rentals
4.8 Average rating
Cupertino stays are highly rated by guests—averaging 4.8 out of 5!
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