
Holiday houses in Cupertino
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Top-rated holiday rentals in Cupertino
Guests agree: these stays are highly rated for location, cleanliness and more.

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)

Cupertino Private Entry Master Suite - Long Stays
Enjoy a serene master bedroom with a private entrance and bathroom in a quiet neighborhood, close to Apple HQ, shops and restaurants Perfect for vacations, business travelers and long-term stays Private & Comfortable: Part of a single-family home with access to large backyard Sleeps 2 Fast WiFi Convenient Location: Near supermarkets and restaurants Laundromat: 2-minute drive Booking: Please read & agree to house rules. Enter correct guest #. Special rates auto-applied for long-term stay

Entire Guesthouse,King Bed in San Jose
Kick back and relax in this calm, stylish space. Whether you're here for a business trip, traveling for pleasure, visiting your friends/relatives, or looking for a short term rental, our fully furnished unit can offer everything you need! Brand-new quiet studio home centrally located. Light and airy with in unit dedicated work-space, washer/ dryer, stove, refrigerator, king bed, microwave with convection oven. Friendly, quiet neighborhood . Everything you need from a home away from home.

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.

Stylish standalone guesthouse near Santana Rowing
Enjoy a stylish experience at this centrally-located guest house in West SJ. Modern finishes and well maintained backyard with gas fireplace for your enjoyment. Queen day bed with pull out twin trundle underneath to sleep up to 3 people. About a 10 minute walk to Santana Row and Valley Fair Mall. Enjoy the booming night life at Santana Row and come back to sleep in a quiet neighborhood. Minutes from SJ Airport, downtown SJ and Campbell, high tech companies and world class eateries.

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.

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.

Beautiful large private studio w/ garden view
Beautiful, large & bright newly-renovated 1Br/1Bath with own separate front entrance. Super convenient on a quiet residential street close to restaurants, supermarkets, and in the heart of Silicon Valley with easy access to tech companies, Universities/colleges and SJ Airport. Furnished with High-end furniture, quality linens and a fireplace. Kitchenette has sink, cabinets, kettle, microwave, fridge and toaster oven. Bath has heating rack for towels and vanity mirror.

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.

Stylish 1bed/1bath apartment in prime location
Stylish 1BR/1BA unit with private balcony in the heart of South Bay. Perfect for solo travelers or couples. Enjoy a modern space with a full kitchen, fast Wi-Fi, smart TV, and dedicated work space. Relax on the balcony or explore nearby cafes, shops, and tech campuses like Apple and Nvidia. Clean, quiet, and conveniently located for work or leisure.

Lush Lux 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
Popular amenities for Cupertino holiday rentals
Other great holiday rentals in Cupertino

Modern & Spacious Guesthouse in Cupertino

Luxury 2 Room Private Bunglow - Executive Suite

Modern Guesthouse With Amenities

An Oasis in Silicon Valley 3 BR/2 Full BA

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

Modern Suite in Cupertino

Monte Sereno Cottage

Premium Guest House-Views-Cupertino Hills- 3Br-2Ba
When is the best time to visit Cupertino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $169 AUD | $169 AUD | $169 AUD | $169 AUD | $183 AUD | $180 AUD | $179 AUD | $173 AUD | $169 AUD | $169 AUD | $172 AUD | $170 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
How much does it cost to stay in guesthouse rentals in Cupertino?
Experience the best of Cupertino with our guesthouse rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there private suite rentals with a dedicated workspace in Cupertino?
Yes! Work meets play with ease at over 10 private suite rentals in Cupertino featuring dedicated workspaces. Stay connected and productive in your home away from home.
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 520 vacation rentals in Rancho Rinconada.
Are there family-friendly house rentals in Cupertino?
Cupertino has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly apartment rentals in Cupertino?
Four-legged friends are welcome in Cupertino. Choose from more than 50 apartment 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!
Do apartment rentals in Cupertino have air conditioning?
Absolutely! We offer over 80 apartment rentals with air conditioning in Cupertino. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Cupertino have wifi?
Absolutely! We offer over 90 apartment rentals with wifi in Cupertino. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Cupertino have a bbq area?
Absolutely! We offer over 10 apartment rentals with a bbq area in Cupertino. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Cupertino have a gym?
Absolutely! We offer over 30 apartment rentals with a gym in Cupertino. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Cupertino

Total holiday rentals
Explore 440 holiday rentals in Cupertino

Nightly prices starting at
Cupertino holiday rentals start at $43 AUD per night before taxes and fees

Verified guest reviews
Over 12,800 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
240 properties have a dedicated workspace

Wi-Fi availability
430 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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