Cupertino holiday rentals

We found 1,154 holiday rentals — enter your dates for availability
Discover a selection of 13 homes 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:18 Dec - 25 Dec

Kitchen
Living room
Exterior
Dining area
Exceptional
(7 reviews)

Pets welcome and no check-out chores at Redwood Grove Retreat!

Boulder Creek

16% off
AU$4,131
for 7 nights, 1 cottage
AU$590 per night
includes taxes & fees
Pets welcome and no check-out chores at Redwood Grove Retreat!
Interior
Island Kitchen & Dining Area
Living area
Living Room
Exceptional
(25 reviews)

Charming Cupertino Retreat: Spacious Home near Apple HQ, Dining and Shopping!

Cupertino

7% off
AU$4,832
for 7 nights, 1 home
AU$690 per night
includes taxes & fees
Charming Cupertino Retreat: Spacious Home near Apple HQ, Dining and Shopping!
Interior
Interior
Private kitchen
Dining
Exceptional
(17 reviews)

Stunning Stylish Luxury 3BR Santa Clara Home

Santa Clara

8% off
AU$2,981
for 7 nights, 1 home
AU$426 per night
includes taxes & fees
Stunning Stylish Luxury 3BR Santa Clara Home
Quiet Private Los Gatos vacation rental home
Quiet Private Magical Los Gatos vacation rental
Dining
Outdoor dining
Wonderful
(12 reviews)

Charming Los Gatos–Saratoga–Monte Sereno Vacation House

Los Gatos

8% off
AU$4,056
for 7 nights, 1 home
AU$579 per night
includes taxes & fees
Charming Los Gatos–Saratoga–Monte Sereno Vacation House
Dining Room
Living room
Living area
Kitchen
Exceptional
(29 reviews)

Bright modern home near Santana Row, Apple

Santa Clara

10% off
AU$4,257
for 7 nights, 1 home
AU$608 per night
includes taxes & fees
Bright modern home near Santana Row, Apple
Property grounds
Pool
Living area
Interior
Exceptional
(8 reviews)

Railway Getaway

San Jose

8% off
AU$2,546
for 7 nights, 1 home
AU$364 per night
includes taxes & fees
Railway Getaway
Living area
Outdoor dining
Room
Dining
Exceptional
(25 reviews)

3M's Luxury Home with fast wifi and private garden near Santana Row

Santa Clara

8% off
AU$5,536
for 7 nights, 1 home
AU$791 per night
includes taxes & fees
3M's Luxury Home with fast wifi and private garden near Santana Row
Interior
Terrace/patio
Interior
Private kitchen
Excellent
(25 reviews)

Serene Guest Suite w/ Private Bath and Kitchenette

San Jose

11% off
AU$812
for 7 nights, 1 home
AU$116 per night
includes taxes & fees
Serene Guest Suite w/ Private Bath and Kitchenette
Kids love the cozy swing on this private deck — fun and relaxing spot for play
Property grounds
Kitchen sink with hanging plants, natural light, and serene backyard views.
Living area
Exceptional
(9 reviews)

Family Favorite-Mickey Dream Loft + TREE house, A Tiny Home Adventure

San Jose

8% off
AU$3,534
for 7 nights, 1 home
AU$505 per night
includes taxes & fees
Family Favorite-Mickey Dream Loft + TREE house, A Tiny Home Adventure
Living area
Interior
Room
Private kitchen
Wonderful
(27 reviews)

Modern 5-Star Oasis - Prime Location in Mountain View #179

Mountain View

8% off
AU$3,563
for 7 nights, 1 home
AU$509 per night
includes taxes & fees
Modern 5-Star Oasis - Prime Location in Mountain View #179
Kitchen
0.2 miles from Castro St and the heart of downtown Mtn View
Kitchen
Kitchen looking to Living Room (furniture will be different)
Exceptional
(42 reviews)

Downtown Private Home With Backyard

Mountain View

10% off
AU$2,796
for 7 nights, 1 home
AU$399 per night
includes taxes & fees
Downtown Private Home With Backyard
Terrace/patio
Interior
Children’s area
Living area
Wonderful
(16 reviews)

Willow Glen Hideaway - Charming Cottage with Hot Tub

San Jose

8% off
AU$1,597
for 7 nights, 1 apartment
AU$228 per night
includes taxes & fees
Willow Glen Hideaway - Charming Cottage with Hot Tub
Property grounds
Entire Guest Suite · Private Cozy Suite Los Gatos,Saratoga,Cupertino
Cozy Suite Entrance
living room Fairy Hill Sanctuary
Exceptional
(10 reviews)

Private Cozy Suite in Monte Sereno–Los Gatos • Walking Distance to Downtown

Los Gatos

8% off
AU$2,430
for 7 nights, 1 apartment
AU$347 per night
includes taxes & fees
Private Cozy Suite in Monte Sereno–Los Gatos • Walking Distance to Downtown
Family Room
2 Short Blocks to Castro St, the heart of Downtown Mtn View
One block to the wonderful Mtn View Public Library
Front of Home
Exceptional
(12 reviews)

Historic Downtown Mountain View Home

Mountain View

11% off
AU$4,197
for 7 nights, 1 home
AU$600 per night
includes taxes & fees
Historic Downtown Mountain View Home
Exterior detail
Living area
Living area
Exterior detail
Exceptional
(6 reviews)

Charming 2-bedroom Loft on Santana Row with WiFi, AC

San Jose

12% off
AU$3,433
for 7 nights, 1 apartment
AU$490 per night
includes taxes & fees
Charming 2-bedroom Loft on Santana Row with WiFi, AC

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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. Winchester Mystery House and Levi's Stadium 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 Andreas Fault Trail (6.5 mi / 10.4 km)
  • Plaza de Cesar Chavez (7.9 mi / 12.7 km)
  • Alum Rock Park (13.8 mi / 22.2 km)
  • Big Basin Redwoods State Park (15.9 mi / 25.6 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, California, the area surrounding the Cupertino Village is an excellent choice. This vibrant neighbourhood is well-known for its convenient access to a variety of dining options and shopping experiences, making it a lively hub for visitors. You'll find a delightful mix of properties, suiting different preferences and budgets, ensuring that you can find something that suits your needs.Another appealing option is the vicinity of Apple Park, where you can marvel at the impressive architecture of the Apple headquarters, which is a point of interest for many tech enthusiasts. The nearby Memorial Park offers a lovely green space for relaxation and outdoor activities, providing a nice balance to the urban environment.
What is the most popular type of holiday rental accomodation in Cupertino?
In Cupertino, apartments are the most popular type of holiday rental, with about 108 available throughout the city. These apartments are often situated in convenient locations, providing easy access to local amenities and attractions such as the Apple Park Visitor Centre. Most apartments come with fully equipped kitchens, comfortable living areas, and some even feature balconies for enjoying the Californian sunshine.For those seeking a bit more space, there are approximately 40 holiday houses available, which are ideal for families or larger groups. These houses typically offer multiple bedrooms, private gardens, and outdoor seating areas, superb for relaxing after a day of exploring. Additionally, several charming cottages can be found in the area, providing a quaint alternative for travellers looking for a unique stay.
Are there any family house rentals in Cupertino?
In Cupertino, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The neighbourhoods here offer a variety of spacious homes, many featuring large living areas, fully equipped kitchens, and outdoor spaces superb for kids to play. Some properties also include amenities such as private gardens, game rooms, and multiple bedrooms to accommodate families comfortably.Visitors to Cupertino can enjoy proximity to local attractions, including the famous Apple Park, which provides a glimpse into the tech giant's innovative spirit. Additionally, nearby parks such as Memorial Park and Cupertino Civic Centre Park offer playgrounds and picnic spots, ideal for family outings.
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 28 options to consider. This suburban area in California is known for its beautiful parks and proximity to technology hubs, making it a convenient choice for both leisure and business travellers.Many of the rentals in Cupertino come equipped with private pools, inviting hot tubs, and spacious outdoor areas great for relaxation and entertaining. Expect amenities such as fully equipped kitchens for self-catering, comfortable living spaces, and often additional features like barbecue grills and landscaped gardens.
Are there pet-friendly house rentals in Cupertino?
In Cupertino, there are several pet-friendly house rentals available, with around 27 options for travellers looking to accommodate their furry friends. The area is known for its suburban charm and proximity to various parks, making it an excellent choice for pet owners. Many of these holiday rentals feature modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like private gardens or patios where pets can roam freely.Nearby, parks such as Blackberry Farm Park and Rancho San Antonio Open Space Preserve provide wonderful opportunities for outdoor activities with pets, including walking trails and picnic areas.
Are there any remote work holiday rentals in Cupertino?
In Cupertino, there are numerous remote work holiday rentals available, with around 36 options to choose from. This vibrant area is well-suited for those looking to blend work and leisure. Many properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas conducive to productivity.Travellers can find rentals situated near popular points of interest, such as the Apple Park Visitor Centre, where you can explore the innovative architecture and enjoy the surrounding gardens. Additionally, the local area boasts a variety of parks and recreational spaces, great for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Cupertino?
In Cupertino, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and coffee or tea makers for a morning boost. Many properties also feature onsite parking, making it convenient for those travelling with vehicles. Additionally, rentals often come with porches or lanais, as well as balconies where visitors can relax and enjoy the pleasant Californian climate.
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 peak season from July to September. This period attracts families and tech enthusiasts alike, as the weather is warm and inviting, superb for exploring the area's attractions. With temperatures typically ranging from 15 to 30 degrees Celsius, visitors can enjoy outdoor activities like hiking in nearby parks and visiting local vineyards.July stands out as the most popular month, bringing a vibrant setting filled with activities and events. It's an excellent time for families to enjoy the local parks and outdoor spaces, where they can partake in picnics or leisurely strolls while soaking in the Californian sun.If you're looking for a more budget-friendly option, consider visiting in October. This month offers a quieter experience, with fewer tourists allowing for a more relaxed atmosphere. The weather remains pleasant, making it a great time to explore Cupertino's charming neighbourhoods and indulge in local cuisine without the hustle and bustle of peak season.
What are the top attractions in Cupertino?
In Cupertino, visitors can explore several attractions that highlight the area's unique character and charm. The Apple Park Visitor Centre offers a fascinating insight into the technology giant's campus, with an impressive architectural design and interactive exhibits. Nearby, the Cupertino Memorial Park provides a lovely green space for picnics and leisurely strolls, featuring walking trails and a picturesque pond.For those interested in nature, the Rancho San Antonio Open Space Preserve offers extensive hiking trails and opportunities for wildlife watching, making it a popular spot for outdoor enthusiasts. The historic De Anza College also hosts cultural events and performances throughout the year, adding to the vibrant community atmosphere.Additionally, the local dining scene in Cupertino is top, with a variety of restaurants offering diverse cuisines, particularly in the area around Wolfe Road and Stevens Creek Boulevard.
Are all fees included in the Cupertino holiday homes prices shown on Stayz?
Stayz 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.
Are there any Cupertino holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Cupertino holiday homes?
You can find great discounts on holiday homes in Cupertino on Stayz, 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.
Can I change or cancel my Cupertino holiday home booking on Stayz?
To find Cupertino holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Cupertino?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Cupertino holiday home?
Book your Cupertino holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Cupertino?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Cupertino to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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