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Cupertino Vacation Rentals

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Our Favorite Vacation Rentals in Cupertino

  • Private Luxury Guest House/ Suite / Executive Retreat
     Home/Apartment
    RedAwning
    From
    $384
  • 3 Private Rooms in a Single Family House Near Apple
    GoodFamily Stay
    Booking.com
    From
    $72
  • Beautiful rooms with garden view in an organic house in Cupertino
     2br Home/Apartment
    HolidayLettings
    From
    $238
  • Extended Stay America San Jose - Mountain View
     Home/Apartment
    NextTrip
    From
    $237
  • Roseview: Dazzling Gem in the Heart of San Jose
     4br Home/Apartment
    RedAwning
    From
    $905
  • 4 bedrooms with 2 bathrooms in a Decent house
    NiceCountry House
    Booking.com
    From
    $54
  • Exquisite Private Studio
     -1br Studio
    HolidayLettings
    From
    $316
  • Luxury 1 bd/1bath Main Street Cupertino apartment
     Home/Apartment
    Booking.com
    From
    $294
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Cupertino Vacation Rentals with a Pool

  • 4bd/2bth newly remodel hourse nr Apple & De anza
    Nice4br Home/Apartment
    Airbnb
    From
    $353
  • Private room 1 near De Anza
     Home/Apartment
    Airbnb
    From
    $96
  • Spacious Suite with Kitchen
    ExcellentHome/Apartment
    Airbnb
    From
    $208
  • Private & Quiet Garden Cottage
    ExcellentHome/Apartment
    Airbnb
    From
    $239
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Cupertino Vacation Rentals with Wi-Fi

  • Beautiful one bedroom in Cupertino, Bay Area
    GoodHome/Apartment
    Airbnb
    From
    $188
  • Ping-Pong | LUXURY | 3Bd/2Ba, 10 mins to Apple HQ
    Good3br Home/Apartment
    Airbnb
    From
    $243
  • Mid Century Modern Guesthouse
    ExcellentHome/Apartment
    Airbnb
    From
    $194
  • Cupertino Business Suites+1G Wifi@Apple
    ExcellentHome/Apartment
    Airbnb
    From
    $235
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Cupertino Pet-Friendly Vacation Rentals

  • Gala Apple 3BR/2BA SFR Backyard, King Bed, Central
     3br Home/Apartment
    HolidayLettings
    From
    $550
  • Perfectly Located Modern 2BR/2BA w/ Gym & Pool
     2br Home/Apartment
    HolidayLettings
    From
    $318
  • Designer 2BR w/ Tuft & Needle Bed, Frette Linens
     2br Home/Apartment
    HolidayLettings
    From
    $292
  • Silicon Valley Luxury Home in Heart of Los Altos - Minutes to Stanford Palo Alto
     5br Home/Apartment
    HolidayLettings
    From
    $1,121
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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.

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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.
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The Weather in Cupertino

Rainy days
89 º50
0
84 º47
0
84 º38
1
65 º36
1
69 º34
3
77 º32
0
81 º36
2
79 º43
1
86 º48
0
93 º48
0
91 º55
0
85 º53
0
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Cupertino. The warmest months in Cupertino are July and June, when temperatures reach 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.

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What Expert Travelers Think

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Vacation Rentals in Cupertino

At AllTheRooms.com we have rentals from all of your favorite providers - Airbnb, Priceline, Agoda and others. We have 731 vacation rentals, hotels and other places to stay in Cupertino ranging from cheap options to extravagant places to stay. A trip to Cupertino can be affordable - our cheapest price vacation rental is available at $17 per night. An average accommodation in Cupertino costs on average $153 a night.

If you have to have an internet connection during your time in Cupertino, then you can choose from over 464 accommodations that have WiFi internet. 36 of our accommodations come with breakfast in the price. Choose from 85 accommodations that provide gym facilities, so you don't miss a single workout. Driving to Cupertino? Then choose one of the 422 places to stay that comes with a parking spot included. 62 accommodations have a a pool or jacuzzi

AllTheRooms has 53 pet-friendly places to stay in Cupertino, so if you're traveling with your cat or dog you won't have any problems.

We combine a wide variety of Cupertino accommodations including vacation rentals, home stays, hostels and other unique places to stay into one easy search. We show results from more than 4 providers, including 454 places to stay from Airbnb, 5 accommodations from Priceline and 3 places to stay from Agoda.

411 of our rentals in Cupertino have been rated by previous guests. They rated 61% as great. You can instantly book any of 233 places to stay right now.

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