Cupertino Vacation Rentals

Our Favorite Vacation Rentals in Cupertino

  • 3 Private Rooms in a Single Family House Near Apple
     Family Stay
    Booking.com
    From
    $72
  • Beautiful rooms with garden view in an organic house in Cupertino
     2br Home/Apartment
    HolidayLettings
    From
    $238
  • Modern Townhome near Apple Campus
     Home/Apartment
    Booking.com
    From
    $270
  • Exquisite Private Studio
     -1br Studio
    HolidayLettings
    From
    $316
  • 4 bedrooms with 2 bathrooms in a Decent house
     Country House
    Booking.com
    From
    $54
  • Sakura room
     Home/Apartment
    HolidayLettings
    From
    $94
  • Separate access to private rooms - Apple Park
     Home/Apartment
    Booking.com
    From
    $141
  • ★ Centrally Located 2B Close to Silicon Valley ★
     2br Home/Apartment
    HolidayLettings
    From
    $292

Check prices for these upcoming dates

Cupertino Vacation Rentals with a Pool

  • Big Studio Near apple & De Anza college
    NiceHome/Apartment
    Airbnb
    From
    $144
  • Private & Quiet Garden Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $239

Cupertino Vacation Rentals with Wi-Fi

  • Private Luxury Guest House/ Suite / Apartment
    ExcellentHome/Apartment
    Airbnb
    From
    $253
  • Guesthouse with kitchen,bath and separate entrance
    ExcellentHome/Apartment
    Airbnb
    From
    $164
  • Beautiful one bedroom in Cupertino, Bay Area
    GoodHome/Apartment
    Airbnb
    From
    $188
  • Cupertino Business Suites+1G Wifi@Apple
    ExcellentHome/Apartment
    Airbnb
    From
    $257

Cupertino Pet-Friendly Vacation Rentals

  • Modern 2br/2ba w/ pool & gym in Perfect Location
     2br Home/Apartment
    HolidayLettings
    From
    $298
  • Executive 2BR/2BA w/ Gym & Pool in New Building
     2br Home/Apartment
    HolidayLettings
    From
    $267
  • Silicon Valley Luxury Home in Heart of Los Altos - Minutes to Stanford Palo Alto
     5br Home/Apartment
    HolidayLettings
    From
    $1,121
  • Cozy Cottage
     Cottage
    HolidayLettings
    From
    $243

Cupertino Travel Guide

Cupertino is located in Santa Clara County right next to San Jose. The city is also right under the wild Santa Cruz Mountains; an excellent place for outdoor activities. Cupertino is part of the Silicon Valley and it is home to the Apple’s headquarters. Interestingly, Cupertino was a small, rural village until the end of the 19th century, but as soon as railroads reached the village it started to develop and grow fast. But the true development and expansion of housing didn't occure until the mid 20th century. Ever since the city has kept growing and developing, welcoming the diverse tech work force that is from all over the world.

Things to Do in Cupertino

Cupertino is not only beautiful but also very interesting because of its place at the forefront of technological advancement. There are also plenty of options for outdoor activities, so the adevnturous types should love Cupertino. Start the Cupertino journey at the Apple Park Visitors Center. The center is an extension of the Apple campus and allows visitors to explore, learn about, and experience Apple's culture (and maybe their plans for world domination). Here guests can purchase various Apple products, see the Apple exhibition, and get cozy on the rooftop terrace. The terrace grants visitors the opportunity to sip on a coffee while overlooking the Infinite Loop Headquarters of Apple, which some say looks like a spaceship.

Another interesting landmark is San Jose's Winchester Mystery House, just a quick drive from Cupertino. While it may just look like an old mansion really it is also the home of some paranormal activity. Built by the wealthy widow of the Winchester fortune there are many oddities like stairs that go nowhere and secret windows looking into rooms throughout the house. There are daily tours which will speak about these peculiarities and talk about the alleged ghosts that live here. The Mystery House is also across the street from Santana Row, an upscale shopping area.

To spend some time outdoors and take advantage of California's weather, visit Rancho San Antonio County Park. The park features a 25 mile long hiking trail and excellent views of the bay. In the heart of the city is Cupertino Memorial Park. A lovely little duck pond, picnic areas, and walking paths are all available for entertainment. The Fujitsu Planetarium is an awesome place to learn about the stars and spend an eye opening afternoon.

Best Places to Stay in Cupertino

The best vacation rentals are near Creekside or the eastern districts where restaurants, cafes, stores, landmarks, and much more are in walking distance. The Stevens Creek area has a large nature preserve essentially in its backyard.

Best Time to Visit Cupertino

The heaviest rain lasts from around April to November, the remaining months are often quite lovely with temperate temperatures ideal for a hike or visiting a nearby winery.

Price and Availability in Cupertino

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Cupertino tends to be Saturday, while the most expensive day tends to be Friday. Vacation homes in Cupertino tend to be busiest on Wednesdays, while it tends to be much quieter on Saturdays.
The most expensive month to stay in a vacation rental in Cupertino is in July, while the cheapest month is in April. The most popular time to book a vacation rental in Cupertino is in the high season in June. Cupertino has its low season in December, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Cupertino

Rainy days
84° 38°
1
65° 36°
1
69° 34°
3
77° 32°
0
81° 36°
2
79° 43°
1
86° 48°
0
93° 48°
0
91° 55°
0
85° 53°
0
89° 50°
0
84° 47°
0
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Cupertino. The hottest month in Cupertino is July, when temperatures peak at 93 ˚F. The coolest month is November, when temperatures drop to 32 ˚F. The wettest month in Cupertino is December with 2.75 inches of rain, while the driest month is November with 0.38 inches of rain.

What Expert Travelers Think

  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
  • — I use and I recommend AllTheRooms because it is a complete platform. It helps to save a lot of time, it gives all the main information about price, location, and features. In a few steps, I can easily find the best place to stay according to my criteria.

    My Anasa
    My AnasaMy Anasa

Vacation Rentals in Cupertino

Browse rentals from all the best providers including Airbnb, Priceline, Agoda and others at AllTheRooms.com. AllTheRooms has 786 rentals, hotels and other great places to stay while you enjoy Cupertino, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. When traveling on a budget, the cheapest place to stay in Cupertino is available at $15 per night. The average price of a rental is around $148 per night.

If you need an internet connection during your stay in Cupertino, then you can choose from over 491 accommodations that provide WiFi internet. 40 places to stay include a breakfast. Choose from 92 places to stay that provide gym facilities, so you don't miss a single workout. If you're planning on arriving in Cupertino by car, be sure to choose from 446 accommodations that provide parking. We track 78 vacation rentals that have a pool or jacuzzi.

If you're traveling with your best friend, then make sure to select one of the 66 pet-friendly accommodations available.

AllTheRooms aggregates vacation rentals, hotels and other bespoke accommodation types from loads of providers in Cupertino, including 493 places to stay from Airbnb, 5 accommodations from Priceline and 3 places to stay from Agoda

422 accommodations in Cupertino have been reviewed; 58% are rated highly. You can instantly book any of 259 places to stay right now.

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