
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)

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.

Contemporary open floor plan home near Santana Row
Centrally-located single family home in West San Jose. Well maintained shared backyard with gas fireplace for your enjoyment. 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 quite neighborhood, so you get the best of both worlds. Minutes from SJ Airport, downtown SJ and Campbell, numerous high tech companies and world class eateries. **NO LARGE GATHERINGS, EVENTS or PARTIES** **NO SMOKING ON PROPERTY**

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.

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.

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.

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.

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.

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

SWEET HOME | Golden Heart Heaven | Prime Location

Luxury 2 Room Private Bunglow - Executive Suite

Simple & Sleek Place- Outdoor dining

Newly built stylish guesthouse

Beautiful large private studio w/ garden view

Modern smart home *RARE* :AppleHQ, SantanaRow !

Modern Suite in Cupertino

"Home Away from Home, 2" in Santa Clara
When is the best time to visit Cupertino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $200 NZD | $210 NZD | $205 NZD | $200 NZD | $217 NZD | $213 NZD | $212 NZD | $205 NZD | $200 NZD | $200 NZD | $203 NZD | $202 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
How much does it cost to stay in house rentals in Cupertino?
Experience the best of Cupertino with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Cupertino?
Yes! Work meets play with ease at over 230 vacation 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 570 vacation rentals in Brookview, over 510 vacation rentals in Monta Vista, and over 510 vacation rentals in Rancho Rinconada.
Are there family-friendly vacation rentals in Cupertino?
Cupertino has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly vacation rentals in Cupertino?
Four-legged friends are welcome in Cupertino. Choose from more than 100 vacation 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 private suite rentals in Cupertino have air conditioning?
Absolutely! We offer over 10 private suite rentals with air conditioning in Cupertino. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cupertino have wifi?
Absolutely! We offer over 220 house rentals with wifi in Cupertino. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cupertino have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Cupertino. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cupertino have a gym?
Absolutely! We offer over 20 house 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 410 holiday rentals in Cupertino

Nightly prices starting at
Cupertino holiday rentals start at $51 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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