Vacation rentals in Cupertino

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Top-rated vacation rentals in Cupertino

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Guest favorite
A stylish blue sofa with tufted detailing is positioned against a light-colored wall. Above the sofa, two framed artworks with gold accents depict lips and the Eiffel Tower. A glass table holds a small arrangement of vibrant orchids in front of the seating area.
Loft in San Jose
4.96 out of 5 average rating, 355 reviews

Stock the Wine Fridge at a Chic Loft on Vibrant Santana Row

Decompress at this serene loft on buzzing Santana Row. Modern glass tiles, custom metal lighting, and an open-plan create a calm, light-filled space with a chic, European-style charm. Relax outside on the cozy bistro table nestled in the palm trees. To meet the strict requirements imposed by the building Home Owners Association, we have added a video doorbell for compliance of noise and potential mis-use of the building and condo. If you need a larger unit on Santana Row please see my other listing by clicking on my profile below or go to this link: www.airbnb.com/rooms/23754461 Chic loft/condo with endless upgrades in the Santana Row Margo building. Modern glass tile & custom paint throughout, upgraded bath with vessel sink. Plush queen platform bed offering a serene & private nights rest. Custom lighting hardware throughout and one FREE dedicated underground parking space in secure garage below the building. Luxury flat is located in the most desirable area in Silicon Valley, Santana Row. "The Row" is an upscale residential, shopping, dining, and entertainment complex in San Jose, California. Everything is within walking distance. There is no need to drive. The condominium is perfect for business travelers or family vacationers. The loft is an open concept layout and has a spacious queen bed with an in-suite full bathroom and closet. The open floor plan includes full size kitchen and living room area. You'll have the entire unit all to yourself. This high end loft has the amenities that you would expect from a world class vacation and executive corporate rental: • Fully furnished luxury loft with large open floor plan. ~740 sq/ft • 1 Queen size bed and full bathroom • If you book for 3 people a High Profile Twin XL size air mattress will be set-up upon your arrival. See pictures as it's a high end air mattress and set up next to kitchen counter. If you only have 2 guest and need two beds you can contact me for pricing and arrangements prior to booking. • If you book for 4 people a High Profile Queen size air mattress will be set-up upon your arrival. See pictures as it will be set up in the living room. • Complimentary Comcast Cable on a 65" HDTV. On Demand is not included • Complimentary High Speed Wi-Fi internet. • One Complimentary assigned underground parking space. • Complimentary Keurig coffee and tea. • Business ready: Wifi, printer, and paper. • Central heating / air conditioning. Nest Thermostat Control • Safe/Security box in the condo for your convenience. • Modern full size kitchen with granite counter tops and major appliances. • In-unit washer and dryer (detergent and softener is included) • Facing the Row for the best people watching spot you could ask for. • No pets • No smoking • Levi's Stadium is close to Santana Row for those wanting to catch a game. Taxi and Uber is available. • If you are looking for a larger unit than check out my other listing on Santana Row by clicking on my profile or this link. • Other listing: https://abnb.me/J4mK5I4DiL The atmosphere of Santana Row is extraordinary! Plenty of restaurants and shops in the area that range from casual to high-end; there is always something to do here. On the other hand there are also salons and spas to pamper yourself. Many restaurants, shops, and entertainment places are within walking distance of this condo. There is no need for a car. Santana Row is also located near a freeway for easy commutes. I'm always available by phone during your stay should you have any questions or issues during your stay. I work close by should you need anything during your stay. Once you're, in I'm hands off unless you need something. Santana Row is an upscale outdoor shopping mall in the heart of San Jose. There are plenty of restaurants and shops ranging from casual to high-end, a CineArts movie theatre, and salons and spas for a relaxing afternoon of pampering. Conveniently location with easy access to highways 101, 880, highway 280, 17 and 87. Major airports: • To SJC (San Jose Airport): 5.9 miles / around 13 min. • To OAK (Oakland International): 37.5 miles / around 43 min. • To SFO (San Francisco International): 37.9 miles / around 45 min. Convention Centers: • 3.7 Miles from San Jose McEnery Convention Center • 7.5 Miles from Santa Clara Convention Center • 3 Miles from SAP Center / HP Pavilion • 8.4 Miles from the brand new Levi's Stadium. Home of the 49'ers. Public transit in San Jose (and the entire South Bay portion of the Bay Area) is provided primarily by VTA, which operates bus and light-rail (modern streetcar) service. Caltrain also provides rail service throughout a portion of Santa Clara County. BART is also an option within the Bay Area. This condo is very clean and kept up to date with no expense spared. The pictures reflect it's current state and there are no surprises. This loft is directly on Santana Row street above Kit & Ace and LuLulemon. From your window you can see Tesla Motors, Straits Cafe, Gucci, and Cocola Bakery. It's really the ultimate location if you are staying on Santana Row or San Jose.

Superhost
The living area is bathed in natural light, showcasing a spacious orange sectional sofa positioned alongside a geometric area rug. A decorative ottoman sits in the center, while a small side table and floor lamp are observed. Tall windows provide a view of palm trees outside.
Loft in San Jose
4.88 out of 5 average rating, 343 reviews

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.

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, 548 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 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
5 out of 5 average rating, 204 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 pull out 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
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, 104 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
A modern living space features a light-colored love seat with two yellow accent pillows. A glass dining table is set with flowers, and a vibrant painting adorns the wall. Natural light enters through the front door, which is flanked by curtains.
Guest suite in Sunnyvale
4.98 out of 5 average rating, 224 reviews

Modern one bedroom in-law unit in Sunnyvale

Modern one bedroom in-law unit using high-end finishing with a comfortable queen bed, private bathroom, full kitchen, work-friendly desk, high speed wifi, cable TV, A/C heater combo and flower-lined side yard. Located in a safe and nice neighborhood. Perfect location for bay area traveller, with easy commute to all major high tech companies, walking distance to supermarket, restaurants and stores, and a short drive to Mountain View downtown and Caltrain station.

Superhost
Home in San Carlos
4.91 out of 5 average rating, 115 reviews

Mid-Peninsula Gem | Peloton + Hot Tub Escape

Welcome to San Carlos, the City of Good Living! Relax in a clean, comfortable home located in a peaceful, safe neighborhood. The space offers fast WiFi, four bedding options, and workspaces. It is just a 7-minute walk to the train and bus stations, with restaurants, coffee shops, and sports bars nearby. I provide complimentary bikes, coffee, and tea. The living room and backyard are set up for guests to enjoy, including access to the hot tub for relaxation.

Guest favorite
A charming cottage exterior is framed by tall cacti and vibrant flower gardens. A welcoming white door with a seasonal wreath invites guests inside. To the side, red chairs provide a cozy seating area, accompanied by a small table, amidst lush greenery.
Guest suite in Los Gatos
4.9 out of 5 average rating, 822 reviews

Charming Hidden Cottage

A home away from home, this hidden little gem is a great getaway from the hustle and bustle of the cities. Still located conveniently close to businesses of all kinds including multiple down town areas, HWY 17 and 85, 1 mile from Netflix. We are constantly working on our cottage style gardens, so there will always be gardens to enjoy for you. If you are interested in trying any of our homegrown veggies or fruits just let us know, we love sharing our bounty:)

Top guest favorite
A rustic caboose, painted in bright red, is nestled among lush green trees. Vintage machinery, featuring large wheels and a copper detail, is positioned nearby, surrounded by a gravel area. The ambiance is quietly rural, under the canopies of towering redwood trees.
Train in Cupertino
4.93 out of 5 average rating, 444 reviews

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.

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, 322 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. 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 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, 298 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.

Top guest favorite
A dining area features a round table surrounded by four white chairs, illuminated by a decorative chandelier. Natural light enters through large windows adorned with sheer curtains, complementing the light green walls and adding a bright, open feel to the space.
Guesthouse in Sunnyvale
4.99 out of 5 average rating, 245 reviews

Lush Lux Villa • Sunny Deck & Private Escape

Romantic private retreat with sunny deck & lush greenery Indoor/outdoor living, vaulted ceilings, garden views Gourmet kitchen, gas fireplace, walk-in shower Heated towel rack, aroma & sound therapy Nest-controlled A/C & heat (no shared ducts) Air filtration + eco-friendly cleaning Self check-in/out, fast WiFi Ideal for couples, solo travelers & business trips

Popular amenities for Cupertino places to stay

When is the best time to visit Cupertino?

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Frequently Asked Questions

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

    Experience the best of Cupertino with our guesthouse rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there private suite rentals with a dedicated workspace in Cupertino?

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

  • 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 family-friendly house rentals in Cupertino?

    Cupertino has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly apartment rentals in Cupertino?

    Four-legged friends are welcome in Cupertino. Choose from more than 50 apartment rentals for guests traveling with pets.

  • Are there Cupertino vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 110 vacation homes with pools in Cupertino, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Cupertino have air conditioning?

    Absolutely! We offer over 80 apartment rentals with air conditioning in Cupertino. Enjoy a tailored experience with all the comforts you desire.

  • 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 apartment rentals in Cupertino have a bbq area?

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

  • Do apartment rentals in Cupertino have a gym?

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

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 € 26 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!