
Holiday houses in Cupertino
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Top-rated holiday rentals in Cupertino
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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)

New! Stylish Condo on Santana Row
Enjoy an indulgent experience at this stylish and centrally-located condo in the heart of Santana Row. "The Row" is a premium blend of residential, retail, and dining spaces in the center of Silicon Valley. Revel in gourmet restaurants, upscale shops, cinemas and a lively atmosphere with outdoor concerts and seasonal festivals. Take a short stroll to Westfield Valley Fair to continue your journey in fine dining, entertainment and shopping venues Located right off of highways 17, 280, and 880.

Santana Row Luxury Executive 2 Story Loft
Beautiful, luxury and clean 2 story open plan loft on the top floor at Margo building right on Santana Row. 2 bedroom 1,5 bath. Panoramic view of the mountains, downtown San Jose and the planes landing at SJC. Your favorite restaurants and shops downstairs. Valley Fair Mall is across the street. Brand new king size bed in the Master Bedroom, walk-in closet, kitchen, Nespresso coffee, teas. Underground parking with EV/Tesla hookup. Security on site 24/7. Ideal for business travelers and families.

Forest Cabin & Hot Tub
Take it easy in this cozy cabin retreat in the Santa Cruz Mountains. 30 minutes from downtown Santa Cruz and beaches. This charming 400 sq. ft. studio is the perfect setting to disconnect from city life and immerse yourself in the redwoods. The cabin features a queen bed, full bathroom, kitchen & BBQ. The private yard includes a hot tub, propane firepit and hammock to fully relax and unwind. Please note the cabin is on a one way, windy road. There is WiFi but no TV or A/C. SCC Permit# 241449

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.

High end home in Silicon Valley, Non-Smokers only
This is a 1 BR/1 BA fully furnished attached house with its own paved private entry way, completely separate from the main house. This is the perfect home away from home while you are relocating, on extended assignment, or on vacation in Silicon Valley. Located in a highly desirable West San Jose residential neighborhood but within 5-minute walking distance to Westgate Mall, Grocery stores, Restaurants, Eateries and Movie Theaters. Street parking available in front of the house.

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

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.

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.

Splendid - Resort Style
Our guest house is surrounded by beautiful gardens and separated from the main house by a sparkling saline pool. Super clean 1 bdrm, private, and contemporary, with a full kitchen and dining/living area. Restorative sleep on the queen sized memory foam bed. The second bed is a high-end, very comfortable queen memory foam pullout located in the living room.
Popular amenities for Cupertino holiday rentals
Other great holiday rentals in Cupertino

Luxury 2 Room Private Bunglow - Executive Suite

Treehouse , San Jose

Modern, Renovated 5b/3ba near Apple, Kaiser

Newly built stylish guesthouse

Beautiful large private studio w/ garden view

Modern Suite in Cupertino

"Home Away from Home, 2" in Santa Clara

Luxury 4-Suite Carbon-Neutral Home With Pool
When is the best time to visit Cupertino?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $163 AUD | $171 AUD | $167 AUD | $163 AUD | $177 AUD | $174 AUD | $172 AUD | $167 AUD | $163 AUD | $163 AUD | $166 AUD | $164 AUD |
| 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 $41 AUD 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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