
Vacation rentals in Cupertino
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Top-rated vacation rentals in Cupertino
Guests agree: these stays are highly rated for location, cleanliness, and more.

Santana Row Loft | Luxe Stay in Silicon Valley
*AIRBNB PLUS ON SANTANA ROW* *Vetted in person by AirBnb* *Creme de la creme of AirBnb* The very spacious open concept condo is over 1090 sq feet of space to enjoy the view from below. This loft unit includes 1 parking spot and a key less door entrance for your convenience and safety. Tall airy ceiling and minimalist decor, VIP guests can unwind after a long day of work/entertainment. The 8 people dining table serves as conference area and work space for remote workers. Enhanced cleaning protocol is implemented between each visit. Some furniture may have moved around the house. Open spacious floor plan. 2 bed/1.5 bath loft condo on top floor with designated parking space below building. Overlooking Santana Row's trendy restaurants and high end shops. The perfect location to spend a weekend of shopping and entertainment. Also, the condo is equipped with office amenities for business travelers - printer, office desk, cable TV, a touch screen computer ( upon request ). We offer name brand king size bed with new Ghost mattress, new fridge and TV in media room/ NEST/ Bluetooth speaker. In addition, we have a small eclectic library for light reading -Coffee/tea - and filtered water for your enjoyment- just send any request in advance and we will try to arrange. If you have a business meeting - the conference table can accommodate up to 8 person. Condo is accessible via underground garage or lobby by key fob. I am available via sms for any questions. I live 40 minutes away - my co host is only 10 minutes away if you need anything. The loft faces the upscale Santana Row shopping district, which is decorated with flowers and a manicured garden. It has a great feel with live bands in the summer, and it's magical in the festive season. Choose from plenty of upscale restaurants. You can walk to the most prestigious shopping center - Westfield Mall - and grocery shop and pharmacy. Spa and restaurants and bar and shopping are only couple of feet away. You may never need to drive. If you have an estimated arrival time later than midnight, please let us know beforehand and we are willing to accommodate your late check-in.

Private Guest-House in the Redwoods
Our custom built guesthouse was completed in 2016. It is situated on 5 redwood-covered acres, 10 minutes south of Los Gatos and 20 minutes from Santa Cruz. We have easy access to hiking and biking trails, world-class wine-tasting, microbreweries, shops, amazing dining, and more! There is something for everyone in our area! We are surrounded by a 35 acre tree farm, so it's very private, yet close to the silicon valley! Our property has a standby generator so we are not affected by power outages.

Sanctuary in Sierra Azul Open Space Preserve
Nestled in the Sierra Azul Mountain Range in Los Gatos, the Sanctuary combines rustic country decor, steampunk original art, state-of-the-art technology with a unique spa experience, providing the perfect private retreat. Surrounded by numerous hiking trails, many friendly animals, and vast wild forest all around us to explore to your liking, along with this exclusive unit serves to provide a refreshing, rejuvenating space to reconnect with your loved one, yourself and of course Mother Nature!

Luxury Silicon Valley Wellness and Work Oasis
Ideal for guests attending matches at Levi’s Stadium, business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

The most desirable & beautiful guesthouse
Centrally located modern guesthouse in Santa Clara. About 10 min drive to Apple Park, Nvidia HQ, Lawrence Caltrain Station, 49ers Levis stadium, Santa Clara Convention Center, Valley Fair Mall/Santana Row, SAP Center/Downtown SJ, SJ Mineta Airport. Your suite will have its own big gourmet Kitchen, specious full bathroom, queen bed with spacious walk in closet, Wi-Fi, TV, desk, and backyard with an outdoor seating area. There is also a shared washer and dryer in the back of the house.

High end home in Silicon Valley, Non-Smokers only
This is a 1 BR/1 BA fully furnished attached house with its own paved private entry way, completely separate from the main house. This is the perfect home away from home while you are relocating, on extended assignment, or on vacation in Silicon Valley. Located in a highly desirable West San Jose residential neighborhood but within 5-minute walking distance to Westgate Mall, Grocery stores, Restaurants, Eateries and Movie Theaters. Street parking available in front of the house.

Caboose in the redwoods just outside of Cupertino
This rustic caboose is just 10 minutes from Cupertino and downtown Saratoga, perfect for both business travelers, outdoor adventurers, and everything in between. There are lots of nearby hiking and biking trails, as well as other exciting outdoor activities. Being so close to Silicon Valley, yet feeling so far from it all is a truly unique experience unlike anywhere else. Pets generally ok. Check with hosts. Pets must not be left alone.

Newly rebuilt ultra clean designer home
Newly renovated ultra clean designer home in duplex minutes from Apple campus. Highly walkable, the entire home has been recently rebuilt from the studs with new top of the line designer furnishings, kitchen essentials, appliances, and toiletries. Disney+, Hulu, Cable TV, and Nespresso coffee included during stay with ultra-fast internet up to 500mbps. 5 min to Whole Foods 12 min to Apple Park 20 min to Stanford

2BR House + Patio + Office near Apple and Main St.
Spacious 2BR + private office in a quiet, walkable neighborhood. 600+ Mbps fiber Wi-Fi, two private parking spots, and a fully stocked kitchen. Just a 3-minute walk to 6 restaurants, 7-minute walk to Cupertino Main Street, and 2-minute drive to Hwy 280 and Lawrence Expressway. Includes two queen beds, smart TVs with streaming, and a backyard garden patio. Perfect for remote work or a comfortable Bay Area stay.

Spacious Business Suite with Serene Backyard View
A master suite with private entrance is within walking distance to Apple Park and Cupertino Main Street. It is located in a quiet Sunnyvale neighborhood and near groceries, and many vibrant restaurants. It features a high speed 1.2G Wifi and split ductless AC. Mountain View corporate commuting bus is nearby. Ample parking space. Everything you need for a successful Silicon Valley visit.

Splendid - Resort Style
Our guest house is surrounded by beautiful gardens and separated from the main house by a sparkling saline pool. Super clean 1 bdrm, private, and contemporary, with a full kitchen and dining/living area. Restorative sleep on the queen sized memory foam bed. The second bed is a high-end, very comfortable queen memory foam pullout located in the living room.

Stylish 1bed/1bath apartment in prime location
Stylish 1BR/1BA unit with private balcony in the heart of South Bay. Perfect for solo travelers or couples. Enjoy a modern space with a full kitchen, fast Wi-Fi, smart TV, and dedicated work space. Relax on the balcony or explore nearby cafes, shops, and tech campuses like Apple and Nvidia. Clean, quiet, and conveniently located for work or leisure.
Popular amenities for Cupertino places to stay
Other great vacation rentals in Cupertino

Luxury 2 Room Private Bunglow - Executive Suite

Modern & Spacious Guesthouse in Cupertino

Sunwoods Mtn. House

Private Guest Suite in Campbell

Beautiful large private studio w/ garden view

Modern Suite in Cupertino

1BR/1BA Near Santana Row | Work-Friendly + Parking

Cupertino Private Entry Master Suite - Long Stays
When is the best time to visit Cupertino?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ433 | ﺩ.ﺇ455 | ﺩ.ﺇ444 | ﺩ.ﺇ433 | ﺩ.ﺇ470 | ﺩ.ﺇ463 | ﺩ.ﺇ459 | ﺩ.ﺇ444 | ﺩ.ﺇ433 | ﺩ.ﺇ433 | ﺩ.ﺇ441 | ﺩ.ﺇ437 |
| Avg. temp | 10°C | 12°C | 13°C | 15°C | 17°C | 19°C | 20°C | 20°C | 20°C | 18°C | 13°C | 10°C |
Frequently Asked Questions
What are the best places to stay in Cupertino?
Main Street and surrounding neighborhoods are often suggested for their easy access to food, shopping, and parks. Family-oriented areas near schools and quiet residential streets can be appealing for travelers seeking a relaxed atmosphere.
What are the best things to do in Cupertino with kids?
Families often explore Memorial Park’s playgrounds, discover wildlife at Rancho San Antonio Open Space Preserve, or engage with interactive history at the Cupertino Historical Society & Museum. Local science and art events offer hands-on learning.
What are some of the best things to do in Cupertino?
Explore the Apple headquarters Visitor Center, stroll through Rancho San Antonio Open Space Preserve, and enjoy recreational activities at Memorial Park. Local restaurants, farmers markets, and cultural events add to the city’s inviting mix.
How is the weather in Cupertino?
Cupertino sees mild winters around 42–59°F (6–15°C), with rain most frequent from November to February. Summers are sunny and dry, typically between 56–77°F (13–25°C), so light layers and sun protection are useful in warmer months.
When is the best time to visit Cupertino?
Late spring and early fall are often recommended for visits, with comfortable temperatures and seasonal events like the Cherry Blossom Festival. Summer has dry, sunny weather, while winter brings moderate rain and cooler days.
What are the best places to visit in Cupertino?
Popular spots include the Apple headquarters Visitor Center, Rancho San Antonio Open Space Preserve, and Memorial Park. Art installations, historical sites, and local shopping centers around Main Street showcase Cupertino’s vibrant character.
What are some hiking trails in Cupertino?
Cupertino has hiking trails at Rancho San Antonio Open Space Preserve, where you can observe wildlife and gentle valleys. Fremont Older Open Space Preserve is also frequently suggested for scenic views and moderate trails.
What are some family activities we can do in Cupertino?
Cupertino has playgrounds, green spaces, and interactive exhibits at the Cupertino Historical Society & Museum. Picnics at Memorial Park, hands-on learning in local science centers, and seasonal community events are frequently suggested for family outings.
What are some of the best day trip ideas from Cupertino?
Day trips often include exploring regional parks, visiting cultural attractions in nearby cities, or discovering wineries and coastal areas around Silicon Valley. Urban adventures and nature walks are frequently suggested for a change of scenery.
Are there any pet friendly accommodations available in Cupertino?
Cupertino has pet-friendly stays, especially in residential neighborhoods and around Main Street. Parks in the area often have walking paths suitable for pets, making it easy to explore the city together.
What are some local tips for visiting Cupertino?
Cupertino has both tech-driven attractions and locally rooted eateries, so take time to explore neighborhoods around Main Street and enjoy diverse cuisine. Comfortable walking shoes are helpful for parks, and many green spaces feature shaded picnic areas.
What is Cupertino known for?
Cupertino is often recognized as the home of Apple’s headquarters and its role in Silicon Valley’s technology scene. The city also has extensive parks, welcoming neighborhoods, and diverse dining reflecting local and global cultures.
What are the best hidden gems to explore in Cupertino?
Explore local parks like Rancho San Antonio Open Space Preserve, which is often recommended for nature walks, or discover community spaces such as the Cupertino Historical Society & Museum. Neighborhood bakeries and small cafes around Main Street frequently surprise with unique flavors.
What are the best foods to try in Cupertino?
Cupertino has a mix of Asian cuisines, locally rooted bakeries, and farm-to-table eateries. Dim sum, ramen, and fusion desserts are frequently suggested, with seasonal produce featured in many menus.
What should I bring for a trip to Cupertino?
Pack light layers and comfortable shoes, as weather varies from cool, rainy winters to warm, sunny summers. Sunscreen and a hat are helpful for outdoor activities, and a reusable water bottle is useful when exploring parks.
What is the nightlife in Cupertino like?
Cupertino has a relaxed nightlife scene, with casual bars, contemporary restaurants, and community gathering spots around Main Street. Live music and social events take place at local venues, with a welcoming, laid-back atmosphere.
What are the most popular events or festivals in Cupertino?
The Cherry Blossom Festival in spring and Diwali Festival in autumn are often recommended, celebrating community and cultural traditions. Cupertino also hosts seasonal outdoor concerts and community gatherings at Memorial Park.
Are there family friendly vacation rentals in Cupertino?
Cupertino has a variety of family-friendly vacation rentals, with options near parks and residential neighborhoods. Many properties provide amenities such as spacious living areas, backyards, and easy access to playgrounds.
Quick stats about vacation rentals in Cupertino

Total vacation rentals
Explore 410 vacation rentals in Cupertino

Nightly prices starting at
Cupertino vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 12,570 verified reviews to help you choose

Family-friendly vacation rentals
130 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 100 rentals that welcome pets

Vacation rentals with a pool
110 properties feature pools

Rentals with dedicated workspaces
230 properties have a dedicated workspace

Wi-Fi availability
410 of Cupertino vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Cupertino rentals

4.8 Average rating
Cupertino stays are highly rated by guests—averaging 4.8 out of 5!
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