Cupertino holiday lettings

We found 1,711 holiday rentals — enter your dates for availability

Discover a selection of 16 homes, 26 apartments and other holiday rentals in Cupertino that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, such as air conditioning and a TV. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Cupertino

Showing deals for:13 Mar - 20 Mar

Image gallery for Mountain cabin w/king suite in the Redwoods of the Santa Cruz Mountains

Exterior
9.8 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)

Mountain cabin w/king suite in the Redwoods of the Santa Cruz Mountains

Boulder Creek, CA

8% off
Price is ÂŁ2,340
for 7 nights, 1 cabin
ÂŁ334 per night
includes taxes & fees
Mountain cabin w/king suite in the Redwoods of the Santa Cruz Mountains

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

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Head to the lively city of Cupertino

Enjoy the area's live music, theatre scene and monuments with a rental holiday home in Cupertino. This welcoming city is known for its restaurants, shopping and cycling. Levi's Stadium and SAP Center at San Jose are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Cupertino

Are you looking for things to do in the area? Venture out of your cosy holiday rental and check out everything that makes Cupertino a one-of-a-kind holiday spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Mountain Winery (4.7 mi / 7.6 km)
  • California's Great America (6 mi / 9.7 km)
  • NASA Ames Research (6.2 mi / 10 km)
  • Twin Creeks Sports Complex (6.5 mi / 10.5 km)
  • Testarossa Winery (8 mi / 13 km)
  • Happy Hollow Park and Zoo (9.3 mi / 15 km)

Exploring the natural features in Cupertino

Whether you're looking for adventure or just want to appreciate the scenery, Cupertino is a great spot to appreciate mother nature. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Silicon Valley (4 mi / 6.4 km)
  • Hakone Gardens (4.9 mi / 7.9 km)
  • San Jose Municipal Rose Garden (5.7 mi / 9.2 km)
  • Vasona Lake County Park (6.5 mi / 10.5 km)
  • Plaza de Cesar Chavez (7.9 mi / 12.7 km)
  • Baylands Nature Preserve (10.2 mi / 16.5 km)

Transport to and around Cupertino

The nearest airport is in San Jose, CA (SJC-Norman Y. Mineta San Jose Intl.), located 6.5 mi (10.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into San Carlos, CA (SQL), which is 17.9 mi (28.8 km) away.

Frequently asked questions

What is the best area to stay in Cupertino when booking a holiday rental?
When considering a holiday rental in Cupertino, a fantastic area to stay in is the neighbourhood surrounding Cupertino Village. This vibrant area offers a delightful mix of dining, shopping, and cultural experiences, making it an ideal base for exploring the town. Close by, you'll find the popular Cupertino Memorial Park, which provides a lovely space for leisurely walks and picnics, as well as recreational facilities. Additionally, the historic De Anza College is nearby, offering a glimpse into the local educational landscape and often hosting various events and exhibitions.

Another excellent option is the area near Vallco Shopping Mall, which has transformed into a hub for entertainment and dining. This neighbourhood is not only convenient for shopping but also provides easy access to various eateries and cafes. A short drive or walk will lead you to the beautiful Rancho San Antonio Open Space Preserve, where you can enjoy stunning natural scenery and hiking trails.
How much does it cost to rent a holiday home in Cupertino?
Prices for holiday rentals in Cupertino vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cupertino to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Cupertino holiday house rentals?
You can find great discounts on house rentals in Cupertino on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Cupertino?
In Cupertino, holiday houses are the most popular type of rental accommodation, with around 30 available throughout the area. These properties generally feature spacious layouts with multiple bedrooms, fully equipped kitchens, and private gardens, making them ideal for families or groups looking to relax after a day of exploring nearby attractions such as the Apple Park Visitor Centre and the beautiful California history trails. Additionally, there are approximately 16 apartments that provide a more compact living space, typically including modern amenities like laundry facilities and communal areas. Cottages are also available, offering a charming and cosy atmosphere for those seeking a quaint getaway.
Can I rent a holiday home with a pool or hot tub in Cupertino?
In Cupertino, there are several holiday homes available for rent that feature pools and hot tubs, with around 36 options to choose from. This charming city, situated in the heart of Silicon Valley, offers a mix of residential neighbourhoods where these properties can be found, including the serene areas near Cupertino Village and the more upscale neighbourhoods like Monta Vista.
Can I find long-stay holiday rentals in Cupertino?
A long-stay holiday rental in Cupertino is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Cupertino?
In Cupertino, there are numerous pet-friendly house rentals available, providing a comfortable stay for travellers accompanied by their furry friends. Many of these properties come with amenities such as spacious backyards, fully equipped kitchens, and modern living areas, making them ideal for families or groups. Some rentals even include features like pet beds and bowls, ensuring your pets feel at home during your stay.

The neighbourhood is known for its beautiful parks, great for pet owners. For instance, the expansive Cupertino Memorial Park offers walking paths and open spaces where pets can enjoy the outdoors. Additionally, the nearby Rancho San Antonio Open Space Preserve provides scenic trails for hiking, allowing you and your pet to explore nature together.
Are there any remote work holiday rentals in Cupertino?
In Cupertino, California, there are numerous remote work-friendly holiday rentals available, with around 35 options to choose from. This vibrant city, known for its high-tech environment and proximity to Silicon Valley, offers a variety of properties equipped to support remote working. Many rentals feature dedicated workspaces, including desks, ergonomic chairs, and computer monitors, ensuring a comfortable setup for productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Cupertino holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Cupertino with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Cupertino?
In Cupertino, popular rental amenities include shared pools, complimentary in-room Wi-Fi, and fitness facilities, suiting travellers' needs for relaxation and connectivity. Many properties also offer onsite parking through third-party services, making it convenient for those driving into the area.
When is the best time to visit Cupertino for a holiday rental?
The best time to visit Cupertino for a holiday rental is during the summer months, particularly in July. This period marks the peak tourist season, where warm, sunny days and a vibrant atmosphere make it ideal for outdoor activities and exploring the delightful surroundings. With temperatures typically ranging between 20 to 30 degrees Celsius, visitors can comfortably enjoy hikes in the nearby hills or stroll through the beautiful parks and gardens.

From July to September, Cupertino comes alive with various events and activities, including outdoor festivals and community gatherings. It's a fantastic opportunity for those seeking a blend of relaxation and fun, with plenty of options for dining, shopping, and sightseeing.

For those looking for a more budget-friendly experience, consider planning your visit in October. This month offers a quieter atmosphere, allowing you to enjoy the stunning autumn foliage in the area and take in the peaceful surroundings without the summer crowds. The mild temperatures in October still make it pleasant for outdoor explorations.
How early should I book a Cupertino holiday rental?
Book your Cupertino holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Cupertino home rental booking on Vrbo?
To find Cupertino holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Cupertino holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCareℱ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCareℱ, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCareℱ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCareℱ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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