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Holiday Rentals in Cupertino

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Our top choices for Cupertino holiday rentals

Kasa University-Airport Santa Clara

Kasa University-Airport Santa Clara
4.0 star property
Santa Clara
9.0 out of 10, Wonderful, (56)
"The unit was spacious, clean, and comfortable. The location is close to SAP Center. There’s a cafe downstairs. Otherwise you need to drive for eateries."
United States
Quynh Huong
The price is €138
includes taxes & fees
19 Dec - 20 Dec
Kasa University-Airport Santa Clara

Modern little poolside house By Downtown Mountain View!

Modern little poolside house By Downtown Mountain View!
Shoreline West
9.4 out of 10, Exceptional, (9)
"This rental was all that I hoped for and I'll try to book it again when I visit my children nearby"
United States
Nancy A.
The price is €241
includes taxes & fees
16 Jan - 17 Jan 2026
Modern little poolside house By Downtown Mountain View!

RainierADU · Spacious CRTL San Jose 1B w/crib free street prkg

RainierADU · Spacious CRTL San Jose 1B w/crib free street prkg
2.0 star property
St. Leo's
10.0 out of 10, Exceptional, (1)
"Our stay was a short one while we were visiting our daughter who lives less than a mile away. We spent most of our time at our daughter’s house and really only slept at this property. It was very clean and well-stocked in a great neighborhood and within walking distance of a number of great eateries and small shops. "
United States
Christiane J.
The price is €279
includes taxes & fees
18 Dec - 19 Dec
RainierADU · Spacious CRTL San Jose 1B w/crib free street prkg

Brand New! Guest House - Modern Stylish & Central

Brand New! Guest House - Modern Stylish & Central
Santa Clara
10.0 out of 10, Exceptional, (43)
"Our stay was great! This was a perfect guest house for our trip! Very clean and in a good neighborhood! "
United States
Shayna C.
The price is €207
includes taxes & fees
18 Dec - 19 Dec
Brand New! Guest House - Modern Stylish & Central

Gourmet Kitchen + Private Front Yard + Parking

Gourmet Kitchen + Private Front Yard + Parking
Burbank
7.6 out of 10, Good, (15)
"The state was pleasant and as described. Property manager made everything very simple and was very responsive. Would highly recommend and would stay here again"
United States
Randy S.
The price is €170
includes taxes & fees
5 Jan - 6 Jan 2026
Gourmet Kitchen + Private Front Yard + Parking

Charming Apartment in the heart of Silicon Valley unit 3

Charming Apartment in the heart of Silicon Valley unit 3
San Jose
9.6 out of 10, Exceptional, (7)
"Good size unit, located very close to Santana Row and Valley Fair. Nice and Clean Apartment!"
United States
Alexander L.
The price is €175
includes taxes & fees
9 Jan - 10 Jan 2026
Charming Apartment in the heart of Silicon Valley unit 3

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, (4)
"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 €290
includes taxes & fees
18 Dec - 19 Dec
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Brand New Guest Suite + Luxurious Bath, Near SJC

Brand New Guest Suite + Luxurious Bath, Near SJC
Burbank
8.0 out of 10, Very good, (16)
"Just a room and a bath in a good locationMet my needs -- would stay there againI recommend it"
United States
Elena L.
The price is €104
includes taxes & fees
21 Dec - 22 Dec
Brand New Guest Suite + Luxurious Bath, Near SJC

Luxury Private Bedroom steps from DT Mt View

Luxury Private Bedroom steps from DT Mt View
2.0 star property
Jackson Park
The price is €141
includes taxes & fees
30 Dec - 31 Dec
Luxury Private Bedroom steps from DT Mt View

Luxury stay near Santana Row for vacation/business

Luxury stay near Santana Row for vacation/business
West San Jose
9.2 out of 10, Wonderful, (51)
"Host was great and very communicative during our stay! Home was clean and felt very cozy! "
United States
Gisselle
The price is €221
includes taxes & fees
30 Dec - 31 Dec
Luxury stay near Santana Row for vacation/business

✨Spacious 2B2B in Sunnyvale 🌲 Patio/AC/1000mb wifi/ more…

✨Spacious 2B2B in Sunnyvale 🌲 Patio/AC/1000mb wifi/ more…
Sunnyvale
9.8 out of 10, Exceptional, (18)
"Very confortable"
United States
Mara R.
✨Spacious 2B2B in Sunnyvale 🌲 Patio/AC/1000mb wifi/ more…

Modern style Santana Row loft

Modern style Santana Row loft
2.0 star property
San Jose
9.0 out of 10, Wonderful, (2)
"The host was very responsive and attentive. Also loved the proximity to Santana Row shopping "
United States
Sue A.
The price is €364
includes taxes & fees
21 Dec - 22 Dec
Modern style Santana Row loft

Suite Walking Distance To Levi`s Stadium

Suite Walking Distance To Levi`s Stadium
2.0 star property
Sunnyvale
The price is €203
includes taxes & fees
20 Dec - 21 Dec
Suite Walking Distance To Levi`s Stadium

Large suite w/ private bath steps from DT Mt View

Large suite w/ private bath steps from DT Mt View
2.0 star property
Jackson Park
The price is €148
includes taxes & fees
17 Jan - 18 Jan 2026
Large suite w/ private bath steps from DT Mt View

Stunning Stylish Luxury 3BR Santa Clara Home

Stunning Stylish Luxury 3BR Santa Clara Home
Santa Clara
10.0 out of 10, Exceptional, (5)
"Neat, clean comfortable, well appointed kitchen, good facilities. A little issue gaining access due to a VRBO glitch so check with the Host to see that has been resolved but I would rent this place again. Minimal "check out" requirements appreciated. "
United States
John M.
The price is €378
includes taxes & fees
18 Dec - 19 Dec
Stunning Stylish Luxury 3BR Santa Clara Home

Private Guest Suite + Full Kitchen, 3 BD, Near SJC

Private Guest Suite + Full Kitchen, 3 BD, Near SJC
Burbank
7.0 out of 10, Good, (7)
"It was convenient, stores and food within walking distance"
United States
Anonymous traveller
The price is €166
includes taxes & fees
21 Dec - 22 Dec
Private Guest Suite + Full Kitchen, 3 BD, Near SJC

San Jose 3b2b near DT & Tech Hub

San Jose 3b2b near DT & Tech Hub
Buena Vista
9.2 out of 10, Wonderful, (13)
"Overall impression was very "
United States
sydney m.
The price is €422
includes taxes & fees
21 Dec - 22 Dec
San Jose 3b2b near DT & Tech Hub

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, (22)
"Nice place and close to Santana Row. Also nice to be close to freeway exit"
United States
Hee Sung K.
The price is €224
includes taxes & fees
6 Jan - 7 Jan 2026
Posh place near Santana Row for vacation/business

Airy Modern 2BR/2BA - Parking + Laundry + Sleep 6

Airy Modern 2BR/2BA - Parking + Laundry + Sleep 6
Shasta-Hanchett Park
9.8 out of 10, Exceptional, (8)
"Ideal location, walking distance from popular San Jose points of interest. House had a great layout and style. Would stay there again."
United States
Liberato M.
The price is €272
includes taxes & fees
18 Dec - 19 Dec
Airy Modern 2BR/2BA - Parking + Laundry + Sleep 6

Spacious 4 Bd 4 Ba home close to all the best of San Jose

Spacious 4 Bd 4 Ba home close to all the best of San Jose
Buena Vista
9.8 out of 10, Exceptional, (48)
"This was an excellent property to stay with my family very convenient as three of the four bedrooms have their own bathroom very clean and very friendly owner we highly recommend this property for his location and space"
United States
Sandra R.
The price is €392
includes taxes & fees
18 Dec - 19 Dec
Spacious 4 Bd 4 Ba home close to all the best of San Jose
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

Everything you need to know about Cupertino holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cupertino holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cupertino holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cupertino holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cupertino. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cupertino holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cupertino holiday rentals we have selected for you start as low as €138 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cupertino rentals

At Expedia, we put the best Cupertino holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cupertino rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cupertino holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cupertino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Cupertino?

Yes, there are holiday rentals in Cupertino close to Bowlmor Lanes, 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?

Mid Century Garden View Home Parking: This holiday home rental outside Cupertino offers a garden and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Cupertino?

Expedia has 16 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. While here, Massage Envy Spa and West Coast Farmers Market are other places worth a visit.

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.