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.

Guest favorite
A modern kitchen and dining area is shown, featuring sleek cabinetry and a marble countertop. A round dining table with two chairs is positioned beside a plush gray sofa. Natural light enters through large windows adorned with blinds, illuminating the light wood flooring.
Home in San Jose
4.86 out of 5 average rating, 188 reviews

Modern House near Apple Park

Welcome to your perfect home away from home! This modern, clean, and peaceful 2-bedroom, 1-bathroom unit features cozy queen-size beds, ideal for a restful stay. Located in an upscale neighborhood, it’s just a 5-minute drive to Apple HQ and shopping centers and a 7-minute walk to supermarkets and a variety of international restaurants. The spacious unit includes a stylish family room, a modern kitchen, and a contemporary bathroom, designed for your comfort and enjoyment.(San Jose/Cupertino area)

Top guest favorite
The spacious interior features rustic wooden walls and exposed beams. A cozy bed with plush bedding is highlighted by warm lighting. A comfortable seating area is nearby, along with a large round mirror and a modern flat-screen TV on the wall.
Guesthouse in Almaden Valley
4.99 out of 5 average rating, 594 reviews

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!

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, 114 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 welcoming living area features a light-colored sofa with red and white cushions. A wooden coffee table with decorative items anchors the space, while vibrant flowers in a vase add a touch of color. A dining area is visible, accompanied by a side chair.
Cottage in Santa Clara
4.94 out of 5 average rating, 210 reviews

Manzanita Cottage in the Heart of Silicon Valley

*We respond to inquiries quickly! We use CDC cleaning guidelines. Our property is powered 100% by solar* The Manzanita Cottage is a perfect getaway for business or vacation travelers. The cottage is well appointed and has everything you need for an extended or short stay. This private & inviting cottage is big on amenities: stove, oven, microwave, coffee maker, dishwasher, washer & dryer, etc. We have two other units on our property: The Orchard tiny house and The Manzanita cottage.

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 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, 443 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.

Top guest favorite
A spacious bedroom features vaulted wooden ceilings and large glass sliding doors leading to an outdoor deck. A comfortable bed is flanked by two bedside tables with lamps. A decorative painting hangs above the bed, and a wooden dresser adds functional storage.
Guesthouse in Woodside
4.99 out of 5 average rating, 571 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

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, 244 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

Guest favorite
A spacious living area features large glass doors that open to a balcony, enhancing natural light. Two round coffee tables are positioned on a textured rug, while a modern TV is mounted on the wall. A mirror and a dining area are visible in the background.
Apartment in San Jose
4.94 out of 5 average rating, 154 reviews

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

When is the best time to visit Cupertino?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,985 ZARR1,985 ZARR1,985 ZARR1,985 ZARR2,153 ZARR2,119 ZARR2,103 ZARR2,035 ZARR1,985 ZARR1,985 ZARR2,019 ZARR2,002 ZAR
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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 R505 ZAR 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!