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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Guest favourite

Home in Sunnyvale

4.97 out of 5 average rating, 274 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!

Jul. 4 – 11

$216 CAD per night

Guest favourite

Guesthouse in Monte Sereno

4.97 out of 5 average rating, 387 reviews

Quiet Poolside Cottage for Solitude

New construction 800 sq. ft. Cottage 1.1 miles to downtown Los Gatos. Off-street parking for one car. Cathedral ceilings with skylight (morning sun, nightly stars). Comfortable pillow top King bed. Single bed in same space for extra guest (extra $25 for third guest/night). Kitchenette with basics. Dining table for work spaces. Pool available for guests. Jacuzzi not available. Many quiet places on property to relax. We do not accept third party reservations. Add your guests on reservation.

Oct. 11 – 18

$225 CAD per night

Guest favourite

Guest suite in Sunnyvale

4.91 out of 5 average rating, 161 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.

Dec. 11 – 18

$173 CAD per night

Guest favourite

Home in San Jose

5.0 out of 5 average rating, 109 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.

Aug. 19 – 26

$223 CAD per night

Guest favourite

Guesthouse in Santa Clara

4.91 out of 5 average rating, 242 reviews

New Construction Clean, Modern, Quiet Cottage

Tranquil, clean new construction cottage completely rebuilt and remodeled from the ground up -- in the heart of Santa Clara with plenty of street parking. Everything a traveler could want under one roof: full kitchen, quartz counters, Bosch washer & dryer, bedroom with cedar accent wall, wall-mounted smart TVs, private zen garden with patio furniture set, ample LED lighting throughout, oversized walk-in shower, high-speed 5.0GHz WiFi, & ample fresh oranges & lemons.

Aug. 11 – 18

$245 CAD per night

Guest favourite

Guest suite in Sunnyvale

4.97 out of 5 average rating, 100 reviews

Private Entrance and Walking to Apple Park

Newly 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.

Aug. 22 – 29

$161 CAD per night

Guest favourite

Guest suite in Cupertino

4.96 out of 5 average rating, 376 reviews

Modern Suite in Cupertino

Nice quiet location. Bright, tranquil, and comfortable unit in a private house with a separate entrance and private yard. Unit consists of one bedroom, one bathroom, and a kitchen and living area. House is within walking distance of Cupertino Library, De Anza College, and top Cupertino schools. Very close to nearby Silicon Valley high-tech companies. Prime Bay Area location with high accessibility to public transporation, eateries, and entertainment.

Jul. 12 – 19

$215 CAD per night

Guest favourite

Guesthouse in San Jose

4.98 out of 5 average rating, 244 reviews

Private cottage in the heart of Silicon Valley

Eden Cottage is our 686 square foot space in west San Jose. It is a custom built (in 2018) 1 Bedroom cottage with a private entrance, super fast WiFi, 50 inch flat screen TV, skylights, full kitchen, a bathroom with a huge shower plus a full sized washer and dryer pair. The cottage is entirely separate from our home and has a small yard and patio under a large oak tree that provides shade to the entire area.

Sep. 25 – Oct. 2

$253 CAD per night

Guest favourite

Guest suite in Campbell

4.99 out of 5 average rating, 135 reviews

Walk to downtown Campbell- Newly renovated suite!

Enjoy our newly remodeled one bedroom suite located next to Downtown Campbell. Whether you're in town for work or leisure, the suite has everything you need including a Queen bed, kitchenette and bathroom. The area is secure, private and safe. This suite is 1 of 2 Airbnbs hosted on the property. 1 Parking spot on the driveway. 0.2 mi to Downtown Campbell (4 min walk!) 3.4 mi to SJC Airport

Oct. 13 – 20

$164 CAD per night

Guest favourite

Home in Cupertino

4.93 out of 5 average rating, 236 reviews

2BR House + Patio + Office near Apple and Main St.

ENHANCED CLEANING routine taking extra care to STERILIZED ALL surfaces especially areas that are often touched or handled. Great for tech-workers looking for a productive spacious staycation. This 2BR home + private office comes w/ blazing fiber internet + 2 parking spots + full kitchen w/ everything + 3 min walk to 5 restaurants & 5 min walk from Downtown Main St

Sep. 27 – Oct. 4

$273 CAD per night

Guest favourite

Guesthouse in Sunnyvale

4.96 out of 5 average rating, 386 reviews

Private cottage in a garden

Charming, private backyard studio cottage nestled in a fenced garden in a quiet Sunnyvale neighborhood. Private, clean and cozy, this 240-sq ft space has a kitchenette, bathroom with shower, full-size bed, Wifi, A/C. Short walk to cafes, groceries. Ample parking.

Feb. 5 – 12

$186 CAD per night

Guest favourite

Guesthouse in Sunnyvale

4.95 out of 5 average rating, 361 reviews

Mid Century Modern Guesthouse

Located in the heart of Silicon Valley, a mid century modern 2 room Eichler style guesthouse with garden views. Private and contemporary, 300sq/ft size space, located in our green backyard. Super clean and new bathroom and interiors.

Jul. 2 – 9

$235 CAD per night