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.

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Top guest favorite
The kitchenette features stylish white cabinetry and open shelving. A coffee maker is placed on a wooden tray, alongside bottles of wine and decorative accessories. A sink with modern fixtures is visible, while a microwave is discreetly housed beneath the counter.
Guesthouse in Willow Glen
4.97 out of 5 average rating, 540 reviews

Stylish, Light-filled Cottage

Eat breakfast on the secluded patio garden at a cozy studio in charming San Jose. Indulge in a relaxing soak in the all-white bathroom, unwind with a book in an antique chair under the sash window, or snuggle up in the carved wooden bed by the fire. The cottage has been fully remodeled. Relax in a brand new king bed and enjoy the all new full bath. Roku TV, AC/Heat and an electric fireplace to relax with. Fully equipped kitchenette and dining area. Private yard to enjoy and relax. Detached cottage, with private, well lit entry. A coded deadbolt lock allows safe entry into cottage. Enjoy a private patio that is also available for guests. We will be giving our guests privacy, but are available by phone or text if you have questions. Willow Glen is the South Bay’s hottest area within San Jose and the Silicon Valley. Downtown is two blocks away, with popular restaurants, banks, antique shops, beauty salons, and coffee houses all close by. Plenty of safe and well lit street parking available. A city bus stop is very close, with freeways, light rail, and Cal train a mile away. Willow Glen is a quaint neighborhood of San Jose, with its charming old homes, and vibrant downtown businesses. Many popular restaurants, banks, antique shops, beauty salons, and coffee houses, just to name a few...all just a short drive or walk away!

Top guest favorite
A bright dining area features a wooden table surrounded by four white chairs. A modern kitchenette with wooden cabinets holds various cooking essentials. Large glass sliding doors provide access to the outdoor patio, allowing natural light to fill the space, while a colorful area rug adds a touch of warmth.
Home in Sunnyvale
4.97 out of 5 average rating, 318 reviews

Comfortable, Modern, Bright w/Patio

A completely separate private guest suite in a beautiful house, furnished with love and all the amenities you'd need. Also, super walkable & safe location, fast wifi, comfy beds, friendly experienced hosts ready to help you with whatever you need. Look forward to soaking in the sun on the patio, and enjoying the park across the street. It's a 10min walk to the great bars & restaurants downtown SV, or to the Caltrain station for a hassle-free trip to SF or SJ. We love living here and so will you!

Top guest favorite
A spacious living area is highlighted by a comfortable sofa adorned with decorative pillows. The open kitchen is visible, featuring modern appliances and a dining table. Large windows allow natural light to fill the room, enhancing the airy atmosphere.
Guesthouse in Santa Clara
4.95 out of 5 average rating, 112 reviews

Santa Clara Guest House w/King Bed and Parking

Newly updated guest house centrally located in the Silicon Valley. Easy access to everything! Close to San Jose Int. Airport, Downtown San Jose, Santa Row, Valley Fair Shopping Center, and more! This stylish guest house will meet all your needs. Fully equipped kitchen with refrigerator, oven/stove, Keurig coffee pot, and dish essentials. Large bedroom with comfortable King bed, en-suite bathroom, laundry, and lots of closet space. Beautiful yard and private drive-way parking included!

Top guest favorite
A view of a stylish entryway features a round mirror above a console table, reflecting a warm atmosphere. A small decorative bowl and candle are placed on the table. In the foreground, a potted plant is arranged in a glass vase, resting on a textured woven mat.
Home in Santa Clara
4.98 out of 5 average rating, 102 reviews

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.

Top guest favorite
A comfortable sleeping area is presented with a spacious bed featuring white linens and a yellow accent pillow. Wall art depicting serene landscapes is displayed above the bed. A small kitchenette with a microwave and coffee bar is located in the corner, adding functionality to the space.
Guest suite in Sunnyvale
4.93 out of 5 average rating, 221 reviews

Luxurious Private Suite in Heart of Silicon Valley

Upscale, private suite w/separate entrance in quiet, safe neighborhood at the center of Silicon Valley! Minutes away from Apple/high tech companies, a cosmopolitan downtown, trendy restaurants, bars, and a historic park for leisurely stroll. Few blocks to US-101, Central Expy, and public transit. Enjoy the warm decor, comfortable queen Beautyrest mattress, luxurious sheets, stalked up coffee bar, private patio overlooking a peaceful back yard as well as unlimited free street parking.

Top guest favorite
The living area features a spacious gray sectional sofa with blue accent pillows, situated adjacent to a wooden coffee table. A patterned rug adds texture to the light wood flooring. Natural light fills the room from the window, which opens to the backyard.
Home in Cupertino
4.95 out of 5 average rating, 319 reviews

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. **www.accesscupertino.com** for 3d tour of interior and videos. 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

Top guest favorite
The bedroom features a spacious bed with neutral-toned bedding, accompanied by a desk and a comfortable chair. A wall-mounted TV and a standing heater are visible. Natural light is allowed in through the window, dressed with sheer curtains, creating a calm environment.
Guesthouse in Cupertino
4.94 out of 5 average rating, 103 reviews

Guesthouse with kitchen,bath and laundry

Private guesthouse/ in-law unit in Cupertino, walking distance from major tech companies with Private entry Convenient access to new restaurants and nightlife. Short commute to freeway and airport. High speed independent internet /Ethernet connection. Comcast streamingTV box, also uverse tv. Airconditioning vent in the bedroom. Wall heater. Portable fans and heater . It includes kitchen, dinette and full bath. It has shared laundry and shared backyard. Nice, quiet neighborhood.

Top guest favorite
The living room features a sleek black sleeper sofa adorned with geometric patterned pillows and a rich red throw. A wooden tray sits atop a gray blanket, and a floor lamp provides soft lighting. A wall art piece depicting a beach scene adds a serene feel to the space.
Home in San Jose
5 out of 5 average rating, 156 reviews

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.

Top guest favorite
A spacious backyard is showcased, featuring lounge chairs arranged on manicured grass. A modern guesthouse with large windows and a bar area is set against lush greenery. Pathways of stone slabs lead to various outdoor seating areas beneath umbrellas, enhancing the space's inviting quality.
Guesthouse in San Jose
4.99 out of 5 average rating, 197 reviews

Stylish standalone guesthouse near Santana Rowing

Enjoy a stylish experience at this centrally-located guest house in West SJ. Modern finishes and well maintained backyard with gas fireplace for your enjoyment. Queen day bed with twin trundle underneath to sleep up to 3 people. About a 10 minute walk to Santana Row and Valley Fair Mall. Enjoy the booming night life at Santana Row and come back to sleep in a quiet neighborhood. Minutes from SJ Airport, downtown SJ and Campbell, high tech companies and world class eateries.

Top guest favorite
A spacious sleeping area features a queen bed with a light, textured blanket and a padded headboard. Subtle pendant lighting hangs above, complementing the large artwork and indoor plant on a wall-mounted shelf. Natural light filters through a nearby window.
Guest suite in Sunnyvale
4.97 out of 5 average rating, 119 reviews

Private Entrance and Walking to Apple Park

Nicely remodeled designer private studio unit. High speed internet 1200 Mbps and 4K Roku-enabled TV Separate external key-code entrance. Separate heating and air conditioning control, handheld remote. Desk area. Spotless attached bathroom. Cathedral wooden ceiling. Super comfortable queen bed, comforter, padded headboard. Zoned, dimmable lighting. Small kitchenette area with counter, microwave, refrigerator, sink, utensils. Friendly, responsive hosts.

Guest favorite
A cozy studio layout is seen, featuring two spacious beds with soft pink bedding. A well-equipped kitchenette is visible in the background, complemented by light-colored cabinetry and modern appliances. Warm lighting from the fixtures creates a peaceful ambiance throughout the room.
Guest suite in San Jose
4.91 out of 5 average rating, 101 reviews

Cozy Studio w/ Private Entrance and bathroom

Cozy Studio within walking distance to Valley Fair & Santana Row! This charming space offers comfort & privacy with its private entrance. Ideal for solo travelers, professionals, or couples, it features a bedroom with two beds. The proximity to O'Connor Hospital makes it perfect for those needing accommodation close to medical facilities. On-premise parking ensures convenience, and the attached private full bathroom guarantees comfort during your stay.

Top guest favorite
The kitchen features wooden cabinetry and stainless steel appliances, with a central island and barstool seating. Natural light floods in through sliding glass doors that lead to a lush outdoor area. A round wooden dining table is set with a small vase containing a flower.
Home in Cupertino
4.94 out of 5 average rating, 294 reviews

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.

Popular amenities for Cupertino vacation rentals

When is the best time to visit Cupertino?

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Avg. priceG$24,655 GYDG$24,655 GYDG$24,655 GYDG$24,655 GYDG$26,745 GYDG$26,327 GYDG$26,118 GYDG$25,282 GYDG$24,655 GYDG$24,655 GYDG$24,655 GYDG$24,655 GYD
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Frequently Asked Questions

  • Where should I stay in Cupertino?

    Make yourself at home in Cupertino by choosing from our most frequently booked neighborhoods. We have over 590 vacation rentals in Brookview, over 520 vacation rentals in Monta Vista, and over 520 vacation rentals in Rancho Rinconada.

  • Are there hotel rentals with a dedicated workspace in Cupertino?

    Yes! Work meets play with ease at over 10 hotel rentals in Cupertino featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in apartment rentals in Cupertino?

    Experience the best of Cupertino with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for Apartment Rentals in Cupertino?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with a gym, over 80 homes with air conditioning, over 90 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Cupertino have wifi?

    Absolutely! We offer over 90 apartment rentals with wifi in Cupertino. Enjoy a tailored experience with all the comforts you desire.

  • Do hotel rentals in Cupertino have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning in Cupertino. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly apartment rentals in Cupertino?

    Four-legged friends are welcome in Cupertino. Choose from more than 40 apartment rentals for guests traveling with pets.

  • Do hotel rentals in Cupertino have a gym?

    Absolutely! We offer over 10 hotel rentals with a gym in Cupertino. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cupertino have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Cupertino. Enjoy a tailored experience with all the comforts you desire.

  • Are there Cupertino hotel rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 hotel rentals with pools in Cupertino, available on Airbnb. Make a splash and soak up the sun in style!

Quick stats about vacation rentals in Cupertino

  • Total vacation rentals

    Explore 440 vacation rentals in Cupertino

  • Nightly prices starting at

    Cupertino vacation rentals start at G$6,268 GYD per night before taxes and fees

  • Verified guest reviews

    Over 12,800 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

    240 properties have a dedicated workspace

  • Wi-Fi availability

    430 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!