Guesthouse vacation rentals in Santa Clara County

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Top-rated guesthouse rentals in Santa Clara County

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

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Guest favorite

Guesthouse in San Jose

4.97 out of 5 average rating, 432 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!

Sep 10 – 17

€ 161 per night

Guest favorite

Guesthouse in Santa Clara

4.92 out of 5 average rating, 109 reviews

Entire guesthouse Santa Clara smart lock entrance.

New remodeled clean and cozy guesthouse in a prime location of Silicon Valley. You will be close to everything when you stay here. Minutes drive to the best Bay Area shopping and dining experiences Santana row and Westfield Valley Fair. Nividia 7min. drive, Apple Park 11 min. drive, Google headquarters Mountain View 15min. Sap center, Levi’s Stadium, and Great America are all nearby. Walk to shops, restaurants and Target shopping center. A close 10 minute drive to San Jose International Airport.

Jan 29 – Feb 5

€ 115 per night

Guest favorite

Guesthouse in San Jose

4.98 out of 5 average rating, 106 reviews

1-bedroom guesthouse w/ full kitchen near DTSJ/SAP

Welcome to our new, 480 sq. ft. backyard cottage, in a quiet neighborhood in downtown West. Walking distance to SAP Center; to Caltrain, Amtrak and VTA station; to restaurants, cafes, breweries, parks, bike/scooter rental, Whole Foods, laundromat, and other amenities. Close to SJ airport, Santana Row, the Rose Garden, the Egyptian Museum, San Pedro Square, Willow Glen, SC convention,SCSU and SJSU. Street parking is plenty n free w/a virtual permit. Pls send ur license plate no. upon arrival.

Sep 22 – 29

€ 132 per night

Guest favorite

Guesthouse in Boulder Creek

4.99 out of 5 average rating, 149 reviews

Digital Nomad Retreat

Imagine yourself in the REDWOOD FOREST and take a breath of mountain air. Only 25 miles from the Silicon Valley, 15 miles from the Santa Cruz Boardwalk, a cozy location tucked in the forest. Many are on the move and can work from anywhere, so why not a beautiful place of your own? A perfect getaway spot central to WINE TASTING, HIKING, BEACHES and even mountain exploration, right from the doorstep. Located only a mile and a half from downtown Boulder Creek, food and window shopping are easy.

Sep 22 – 29

€ 164 per night

Guest favorite

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.

Sep 10 – 17

€ 155 per night

Guest favorite

Guesthouse in San Jose

5.0 out of 5 average rating, 111 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.

Nov 29 – Dec 6

€ 183 per night

Guest favorite

Guesthouse in Santa Cruz

4.97 out of 5 average rating, 629 reviews

Upper WS Guesthouse-2mi. from UC, Downtown & Beach

This detached guesthouse, recently updated in May 2023, is 500 sq. ft and 20ft. away from the main house. It’s located up the driveway & tucked away on the right side of the property. Perfect for 2 people but can sleep 3-4 (convertible couch OR queen air mattress). Close to popular destinations such as: UC Santa Cruz campus (approx. 2 miles), Boardwalk, desired beaches (approx. 2 miles), downtown Santa Cruz, hiking trails etc. Fully furnished guesthouse w/washer & dryer.

May 19 – 24

€ 177 per night

Guest favorite

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 22 – 29

€ 178 per night

Guest favorite

Guesthouse in Los Gatos

4.97 out of 5 average rating, 862 reviews

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

Jul 19 – 26

€ 224 per night

Guest favorite

Guesthouse in San Jose

4.94 out of 5 average rating, 142 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)

Jul 8 – 15

€ 111 per night

Guest favorite

Guesthouse in San Jose

4.8 out of 5 average rating, 141 reviews

Lovely & Cozy 1b1b Guest Cottage Downtown San Jose

Our lovely and cozy cottage is in the heart of Silicon Valley, Japantown/Downtown San Jose. just minutes from SJSU, SAP center, San Jose McEnery Convention Center, fantastic restaurants, bars, SJC airport(10 min drive), Levi’s stadium(15 min drive). Public transportation is also nearby. We also have a wonderful yard including palm trees and coconut trees! NO PARTIES. NO EVENTS. REGUALAR STAY ONLY!!!

Oct 9 – 16

€ 120 per night

Guest favorite

Guesthouse in Sunnyvale

4.96 out of 5 average rating, 387 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 15 – 22

€ 128 per night