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Holiday houses in Cupertino

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Top-rated holiday rentals in Cupertino

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in Cupertino
4.98 out of 5 average rating, 59 reviews

Cupertino Private Entry Master Suite - Long Stays

Enjoy a serene master bedroom with a private entrance and bathroom in a quiet neighborhood, close to Apple HQ, shops and restaurants Perfect for vacations, business travelers and long-term stays Private & Comfortable: Part of a single-family home with access to large backyard Sleeps 2 Fast WiFi Convenient Location: Near supermarkets and restaurants Laundromat: 2-minute drive Booking: Please read & agree to house rules. Enter correct guest #. Special rates auto-applied for long-term stay

Top Guest favourite
An outdoor pool area features a long, picturesque pool bordered by vibrant greenery. Large green pool floats rest on the water, complemented by a shaded lounge area under a white umbrella. The space showcases brick pathways and stone details of the home’s exterior.
Home in Los Altos
4.93 out of 5 average rating, 394 reviews

Pool, Hot tub, Sauna I Your Silicon Valley Luxury

Upscale Los Altos Hills. Peaceful and spacious 1,500 sq. ft. retreat. Ideal for business travelers, couples, nature lovers. Adjacent to 3,988-acre Rancho San Antonio Preserve with direct trail access, wildlife, serenity. Inside: workspace with fiber-optic Wi-Fi, fireplace, sauna, pool table, fully equipped kitchen and plush queen bed with guest praised mattress. Outside: exclusive access to saline heated pool and hot tub, patio with BBQ. Minutes from Stanford, Palo Alto, and top tech campuses.

Guest favourite
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, 305 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 favourite
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, 100 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 favourite
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, 187 reviews

Stylish standalone guesthouse near Santana Row

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.

Guest favourite
The exterior of the home features a single-story structure with a warm-toned brick facade. Lush plants and blooming flowers surround the entrance, enhancing the welcoming appearance. A clear blue sky above adds a bright backdrop to the setting.
Guest suite in Sunnyvale
4.93 out of 5 average rating, 114 reviews

Beautiful large private studio w/ garden view

Beautiful, large & bright newly-renovated 1Br/1Bath with own separate front entrance. Super convenient on a quiet residential street close to restaurants, supermarkets, and in the heart of Silicon Valley with easy access to tech companies, Universities/colleges and SJ Airport. Furnished with High-end furniture, quality linens and a fireplace. Kitchenette has sink, cabinets, kettle, microwave, fridge and toaster oven. Bath has heating rack for towels and vanity mirror.

Guest favourite
A studio space features sloped ceilings with natural light from skylights. A full-sized bed is dressed in patterned linens, accompanied by a 43-inch smart TV on a low wooden console. A single armchair with an ottoman is positioned near a dark dresser.
Guesthouse in Hensley
4.94 out of 5 average rating, 223 reviews

Private Entrance Studio with in-unit bathroom

Private entrance studio with in-unit bathroom and wet bar, it is located near downtown San Jose and Japantown. 2 min walk to the light rail station (japantown ayer green/blue lines), great for someone traveling or on a business trip. Few minutes drive to Target, Trader Joe, grocery stores, San Pedro Square. This studio unit is converted from the attic of detached garage structure with excellent privacy (1st floor is used as storage) *street parking only*

Guest favourite
A comfortable living area features two gray sofas, an accent coffee table, and a television mounted on the wall. Natural light enters through two windows adorned with sheer coverings. Wall art in warm tones adds a subtle touch, enhancing the inviting mood of the space.
Guest suite in Sunnyvale
4.89 out of 5 average rating, 143 reviews

One Bedroom Suite between Apple and Google campus’

Clean beautiful one bedroom suite/Guest house located in quiet neighborhood in Sunnyvale. Unshared private entrance and easy parking. Conveniently located between main Apple campuses. (Mothership, Infinite Loop and Arques campus) and Googleplex. Full kitchen with all amenities, washer/dryer/iron and ironing board, hair dryer, Wifi, TV and comfortable work area. Easy assess to all major freeways mostly with reverse commute.

Top Guest favourite
A bright sleeping area features a spacious bed with white bedding and a decorative throw. Two bedside lamps illuminate the room, while colorful animal artwork adorns the wall above. A cozy sofa and a small side table complete the inviting atmosphere.
Guest suite in San Jose
4.94 out of 5 average rating, 652 reviews

Walk to Santana Row + Valley Fair | 6min drive SJC

Private guest suite with it's own front door, bedroom and bathroom. There is no kitchen but we provide a mini fridge, microwave and kettle. It is a short walk to Santana row and Valley Fair Mall and a 5 minute drive to SJC Airport. This suite is 1 of 2 Airbnbs on the property. 1 Parking spot on the driveway, directly in front of the Airbnb. 0.3 mi to Santana Row 0.3 mi to Westfield/Valley Fair 3.1 mi to SJC Airport

Top Guest favourite
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, 285 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.

Guest favourite
The exterior of the master suite is showcased, featuring a pathway leading to a glass door. Vibrant yellow flowers and greenery frame the entrance, while a tree provides shade. The space is surrounded by a gravel yard and clear blue skies.
Guest suite in Sunnyvale
4.95 out of 5 average rating, 111 reviews

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.

Top Guest favourite
The inviting saline pool is surrounded by a spacious patio featuring comfortable lounge chairs and shaded areas. Lush greenery and colorful gardens frame the scene, while the contemporary guest house provides easy access to the pool, enhancing the tranquil outdoor ambiance.
Guesthouse in Los Altos
4.98 out of 5 average rating, 376 reviews

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.

Popular amenities for Cupertino holiday rentals

When is the best time to visit Cupertino?

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Avg. price$206 NZD$206 NZD$206 NZD$206 NZD$224 NZD$220 NZD$204 NZD$206 NZD$206 NZD$206 NZD$206 NZD$206 NZD
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Quick stats about holiday rentals in Cupertino

  • Total holiday rentals

    Explore 440 holiday rentals in Cupertino

  • Nightly prices starting at

    Cupertino holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 12,460 verified reviews to help you choose

  • Family-friendly holiday rentals

    130 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 100 rentals that welcome pets

  • Holiday rentals with a pool

    110 properties feature pools

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

  • Wi-Fi availability

    440 of Cupertino holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Cupertino rentals

  • 4.8 Average rating

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