Holiday Rentals in Cupertino

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Our top choices for Cupertino holiday rentals

Luxury stay near Santana Row for vacation/business

Luxury stay near Santana Row for vacation/business
West San Jose
9.4 out of 10, Exceptional, (60 reviews)
"Everything was nice and perfect! it felt like our second home and getting thru the city was nice as well. I loved how it was close by to the mall and everything."
United States
Vanessa
The price is €225
includes taxes & fees
8 Jun - 9 Jun
Luxury stay near Santana Row for vacation/business

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 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 €283
includes taxes & fees
13 May - 14 May
Brand New Private One Bedroom Cottage with a Wet Bar/Kitchenette

Modern little poolside house By Downtown Mountain View!

Modern little poolside house By Downtown Mountain View!
Shoreline West
9.4 out of 10, Exceptional, (10 reviews)
"Very welcome host, great amenities"
United States
Anna J.
Modern little poolside house By Downtown Mountain View!

Gourmet Kitchen + Private Front Yard + Parking

Gourmet Kitchen + Private Front Yard + Parking
Burbank
7.6 out of 10, Good, (20 reviews)
"Great location, clean, friendly owners. "
United States
Brian L.
The price is €186
includes taxes & fees
8 Jun - 9 Jun
Gourmet Kitchen + Private Front Yard + Parking

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, (26 reviews)
"Perfect gem! Great location, clean property. Very professional and kind host. "
United States
S R.
The price is €231
includes taxes & fees
13 May - 14 May
Posh place near Santana Row for vacation/business

"Luxury: 4B/3B with Dual EnSuites, Parking, WiFI"

"Luxury: 4B/3B with Dual EnSuites, Parking, WiFI"
West San Jose
8.2 out of 10, Very good, (11 reviews)
"We loved our stay, although short, in this comfy home. Our dog loved the sunny yard and we really enjoyed our time there overall!!"
United States
claire p.
The price is €445
includes taxes & fees
13 May - 14 May
"Luxury: 4B/3B with Dual EnSuites, Parking, WiFI"

San Jose 3b2b near DT & Tech Hub

San Jose 3b2b near DT & Tech Hub
Buena Vista
9.0 out of 10, Wonderful, (18 reviews)
"The house was very well equipped and perfect for our family"
United States
Valentina
The price is €460
includes taxes & fees
21 May - 22 May
San Jose 3b2b near DT & Tech Hub

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 €328
includes taxes & fees
13 May - 14 May
Santana Row Properties #7 - Silicon Valley Getaway

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, (9 reviews)
"Suitable for the family. Within walking distance of where we wanted go."
United States
Michael A.
The price is €259
includes taxes & fees
27 May - 28 May
Airy Modern 2BR/2BA - Parking + Laundry + Sleep 6

Modern style Santana Row loft

Modern style Santana Row loft
San Jose
9.6 out of 10, Exceptional, (5 reviews)
"The host was very responsive and attentive. Also loved the proximity to Santana Row shopping "
United States
Sue A.
The price is €413
includes taxes & fees
31 May - 1 Jun
Modern style Santana Row loft

Kasa University-Airport Santa Clara

Kasa University-Airport Santa Clara
4.0 star property
Santa Clara
9.0 out of 10, Wonderful, (64 reviews)
"Clean room and nice amenities"
United States
Olivia
The price is €143
includes taxes & fees
14 May - 15 May
Kasa University-Airport Santa Clara

Santana Row Properties #3 - Silicon Valley Getaway

Santana Row Properties #3 - Silicon Valley Getaway
San Jose
Santana Row Properties #3 - Silicon Valley Getaway

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, (7 reviews)
"Nice place and great location."
United States
Rhonda
The price is €333
includes taxes & fees
13 May - 14 May
Luxury 1 bedroom apartment in Santana Row, San Jose

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, (8 reviews)
"Easy stay, walking distance to Santana Row. "
United States
Eric H.
The price is €176
includes taxes & fees
27 May - 28 May
Charming Apartment in the heart of Silicon Valley unit 3

Charming 3-bedroom Guesthouse with WiFi in Sunnyvale

Charming 3-bedroom Guesthouse with WiFi in Sunnyvale
San Miguel
The price is €623
includes taxes & fees
13 May - 14 May
Charming 3-bedroom Guesthouse with WiFi in Sunnyvale

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, (55 reviews)
"This home with 4 bedrooms and 4 bathrooms was perfect for 8 of us. Kitchen was great, not alot of pans or utensils but we always bring ours cause my son has celiac. Beautiful home and comfy. Close to downtown, easy access to SAP Center. We would definitely stay again. "
United States
Nichole D.
The price is €391
includes taxes & fees
1 Jun - 2 Jun
Spacious 4 Bd 4 Ba home close to all the best of San Jose

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 reviews)
"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 €99
includes taxes & fees
17 May - 18 May
Brand New Guest Suite + Luxurious Bath, Near SJC

Brand New! Guest House - Modern Stylish & Central

Brand New! Guest House - Modern Stylish & Central
Santa Clara
10.0 out of 10, Exceptional, (44 reviews)
"I have stayed here a few times now and its my go-to when I am in town. This location is always clean and its in a great location!"
United States
Kai S.
The price is €218
includes taxes & fees
30 May - 31 May
Brand New! Guest House - Modern Stylish & Central

Big 6BR DT SJ Getaway + Huge Backyard

Big 6BR DT SJ Getaway + Huge Backyard
Ryland
10.0 out of 10, Exceptional, (3 reviews)
"This house was perfect for our group of 10 as a place to stay while we were in the area to see a SJ Sharks game as it was only a 5 min drive from SAP Center. It was very a beautiful home that was clean, comfortable, and perfect for a large group. Our host was very responsive anytime I reached out. We had asked if the home had any extra blankets - they responded immediately and had brand new blankets delivered within the hour. If we found ourselves in SJ with a large group we would absolutely...
United States
Jen S.
The price is €609
includes taxes & fees
1 Jun - 2 Jun
Big 6BR DT SJ Getaway + Huge Backyard

Stylish Central San Jose 3B2B w/crib Free Parking

Stylish Central San Jose 3B2B w/crib Free Parking
St. Leo's
9.6 out of 10, Exceptional, (8 reviews)
"Location was great and the home was nice. "
United States
Matt K.
Stylish Central San Jose 3B2B w/crib Free Parking
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 €99 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?

Spacious Getaway – Hot Tub, Big Yard, Near Beach, pet friendly, Great for All!: This holiday home rental outside of Cupertino offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Cupertino?

Expedia has 13 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 Cupertino Historical Society and Museum and McClellan Ranch Park. While here, Blackberry Farm Golf Course 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.