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Cupertino Holiday Rentals

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Our top choices for Cupertino holiday rentals

1. Kasa University-Airport Santa Clara

Kasa University-Airport Santa Clara
4.0 star property
Santa Clara
9.0 out of 10, Wonderful, (76 reviews)
"Clean room. Nicely appointed. Laundry was very useful. Would stay again."
United States
Bryce
The price is NZ$255
includes taxes & fees
27 Sept - 28 Sept
Kasa University-Airport Santa Clara

2. Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette
Cupertino
9.6 out of 10, Exceptional, (5 reviews)
"This property is located in a residential and quiet neighborhood with a nice park within walking distance! Great place for someone who is traveling by themselves!"
United States
Kevin
The price is NZ$552
includes taxes & fees
9 Sept - 10 Sept
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

3. Comfy 2BR Apt w/ AC/Washer/Dryer/EV - in Sunnyvale

Comfy 2BR Apt w/ AC/Washer/Dryer/EV - in Sunnyvale
Sunnyvale West
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay"
United States
Christopher C.
Comfy 2BR Apt w/ AC/Washer/Dryer/EV - in Sunnyvale

4. 💎Cozy 1B/1B in a prime location • 🌲AC/ 1000mb wifi/ Washer, dryer/ more…

💎Cozy 1B/1B in a prime location • 🌲AC/ 1000mb wifi/ Washer, dryer/ more…
Sunnyvale
9.8 out of 10, Exceptional, (11 reviews)
"Great location, quiet and quaint. "
United States
Karen B.
The price is NZ$471
includes taxes & fees
14 Sept - 15 Sept
💎Cozy 1B/1B in a prime location • 🌲AC/ 1000mb wifi/ Washer, dryer/ more…

5. Upscale Bay Area themed place near Santana Row

Upscale Bay Area themed place near Santana Row
West San Jose
9.8 out of 10, Exceptional, (8 reviews)
"Place was beautiful. Very convenient to westfield mall and Santana row. "
United States
Kelly L.
The price is NZ$493
includes taxes & fees
21 Sept - 22 Sept
Upscale Bay Area themed place near Santana Row

6. 🌟 Stylish 2B2B Retreat in the Heart of the Silicon Valley

🌟 Stylish 2B2B Retreat in the Heart of the Silicon Valley
Sunnyvale
9.4 out of 10, Exceptional, (10 reviews)
"This property was exceptional! The cleanliness was impeccable, the space was spacious, and the amenities provided were abundant. The location was perfect, with numerous restaurants and a grocery store within easy walking distance. Highly recommended for a comfortable and convenient stay. 5 stars!"
United States
maggie c.
The price is NZ$656
includes taxes & fees
9 Sept - 10 Sept
🌟 Stylish 2B2B Retreat in the Heart of the Silicon Valley

7. Posh place near Santana Row for vacation/business

Posh place near Santana Row for vacation/business
West San Jose
9.6 out of 10, Exceptional, (30 reviews)
"Great place to stay "
United Kingdom
Dan M.
The price is NZ$460
includes taxes & fees
9 Sept - 10 Sept
Posh place near Santana Row for vacation/business

8. Luxurious Stunning Resort Like House in Silicon Valley 1GBPS 4 beds/2 baths

Luxurious Stunning Resort Like House in Silicon Valley 1GBPS 4 beds/2 baths
Cupertino
10.0 out of 10, Exceptional, (7 reviews)
"The rental was a beautiful and spacious property. Jennifer was extremely helpful and her communication was some of the best I’ve experienced when using Airbnb. I would highly recommend this rental!"
United States
Grant H.
The price is NZ$1,630
includes taxes & fees
20 Sept - 21 Sept
Luxurious Stunning Resort Like House in Silicon Valley 1GBPS 4 beds/2 baths

9. Modern style Santana Row loft

Modern style Santana Row loft
San Jose
9.4 out of 10, Exceptional, (10 reviews)
"No major complaints, great stay and nice area. The AC is not very good so it does get hot and stuffy unfortunately."
United States
Kenneth L.
The price is NZ$746
includes taxes & fees
13 Sept - 14 Sept
Modern style Santana Row loft

10. Santana Row Properties #7 - Silicon Valley Getaway

Santana Row Properties #7 - Silicon Valley Getaway
San Jose
9.8 out of 10, Exceptional, (36 reviews)
"Great location and easy to navigate the area"
United States
Jennifer B.
The price is NZ$869
includes taxes & fees
13 Sept - 14 Sept
Santana Row Properties #7 - Silicon Valley Getaway

11. Cupertino 2BR w/AC/Washer/Dryer/EV on 1F

Cupertino 2BR w/AC/Washer/Dryer/EV on 1F
Sunnyvale West
The price is NZ$633
includes taxes & fees
5 Oct - 6 Oct
Cupertino 2BR w/AC/Washer/Dryer/EV on 1F

12. Charming 1-bedroom house in superb San Jose with AC, WiFi

Charming 1-bedroom house in superb San Jose with AC, WiFi
West San Jose
5.2 out of 10, (5 reviews)
"When we went to the place we had issues finding our way to enter the property the landlord was able to give me some information about how to get in. The she mentioned she forgot to clean the place. We got in and found used towels all around with weird smell. The places wasn’t cleared. And what she offered to solve was to wait like 2 hours for her to arrive that will give us clean bed sheets for us to change. We had driven a lot to find where we stay will be clean at least. So we managed to...
United States
Julio M.
The price is NZ$322
includes taxes & fees
18 Sept - 19 Sept
Charming 1-bedroom house in superb San Jose with AC, WiFi

13. Big Room Queen Bed & Sofa Bed/ Perfect environment

Big Room Queen Bed & Sofa Bed/ Perfect environment
Sunnyvale
The price is NZ$416
includes taxes & fees
9 Sept - 10 Sept
Big Room Queen Bed & Sofa Bed/ Perfect environment

14. @ Marbella Lane - Convenient Home in Sunnyvale

@ Marbella Lane - Convenient Home in Sunnyvale
Sunnyvale
9.4 out of 10, Exceptional, (13 reviews)
"Great stay, thank you for hosting us!"
United States
Vladimir T.
The price is NZ$831
includes taxes & fees
13 Sept - 14 Sept
@ Marbella Lane - Convenient Home in Sunnyvale

15. Luxury 1 bedroom apartment in Santana Row, San Jose

Luxury 1 bedroom apartment in Santana Row, San Jose
San Jose
9.8 out of 10, Exceptional, (11 reviews)
"Wonderful stay!"
United States
Kristie M.
The price is NZ$664
includes taxes & fees
13 Sept - 14 Sept
Luxury 1 bedroom apartment in Santana Row, San Jose

16. Global Luxury Suites at Mountain View

Global Luxury Suites at Mountain View
4.0 star property
Shoreline West
8.2 out of 10, Very good, (196 reviews)
"Extremely terrible check in experience "
United States
Jiajun
The price is NZ$835
includes taxes & fees
17 Sept - 18 Sept
Global Luxury Suites at Mountain View

17. Charming Apartment in the heart of Silicon Valley unit 3

Charming Apartment in the heart of Silicon Valley unit 3
San Jose
9.4 out of 10, Exceptional, (9 reviews)
"Easy stay, walking distance to Santana Row. "
United States
Eric H.
The price is NZ$346
includes taxes & fees
11 Sept - 12 Sept
Charming Apartment in the heart of Silicon Valley unit 3

18. Downtown 1bd/1ba ADU

Downtown 1bd/1ba ADU
Heritage District
10.0 out of 10, Exceptional, (1 review)
"This location was FANTASTIC! I really didn’t realize when I booked how close it was to the CalTrain to go to San Francisco which made our weekends SO easy! It also had the cutest shopping area on the other side of the train that met all our needs. The room apartment was spacious and clean, and even had a tub which I didn’t realize was so rare in California lol! And even though there was an accident with a pipe in the laundry room, the host made sure it was clean and accessible! It was a truly...
United States
Kayla P.
The price is NZ$541
includes taxes & fees
27 Sept - 28 Sept
Downtown 1bd/1ba ADU

19. Gourmet Kitchen + Private Front Yard + Parking

Gourmet Kitchen + Private Front Yard + Parking
Burbank
8.0 out of 10, Very good, (31 reviews)
"Great location, clean, friendly owners. "
United States
Brian L.
The price is NZ$292
includes taxes & fees
11 Sept - 12 Sept
Gourmet Kitchen + Private Front Yard + Parking

20. Santana Row Properties #6 - Silicon Valley Getaway

Santana Row Properties #6 - Silicon Valley Getaway
San Jose
10.0 out of 10, Exceptional, (19 reviews)
"This apartment is in such a great location right on Santana Row where there is really nice shopping and restaurants. The bed was super comfortable and the amenities were great. I will definitely be staying here again."
United States
Wendy C.
The price is NZ$911
includes taxes & fees
21 Sept - 22 Sept
Santana Row Properties #6 - Silicon Valley Getaway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cupertino Hotel Reviews

Find out more about Cupertino

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cupertino holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cupertino. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cupertino. Seeing all the best attractions is bound to make you fall in love with Cupertino. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cupertino short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Cupertino?

Yes, there are holiday rentals in Cupertino close to Labyrinth 1, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Cupertino. The live music and theatre scene are some other things you might like to check out during your trip.

What are some of the best holiday rentals that Cupertino has to offer?

Serene Guest Suite w/ Private Bath and Kitchenette: This holiday home rental outside of Cupertino has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Cupertino?

Expedia has 12 holiday rentals for your stay in Cupertino.

What’s there to see and do in Cupertino?

Enjoy the outdoors at Silicon Valley and Santa Cruz Mountains, or simply take in cultural attractions like McClellan Ranch Park and Cupertino Historical Society and Museum. In the wider area, you’ll find popular places such as Levi's Stadium and SAP Center at San Jose.

What are holiday rentals like in Cupertino?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cupertino. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.