Guesthouse vacation rentals in San Jose

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Top-rated guesthouses in San Jose

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

Guest favourite
Guesthouse in San Jose
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!
Aug. 4 – 11
$238 CAD per night
4.97 out of 5 average rating, 419 reviews
Guest favourite
Guesthouse in Santa Clara
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.
Dec. 10 – 17
$187 CAD per night
4.91 out of 5 average rating, 102 reviews
Guest favourite
Guesthouse in San Jose
TheStudio in Willow Glen (San Jose) CA-95125
Detached Studio, ideal for travel refuge, those needing fast and reliable internet for meetings, vacationers, and extended family. ALL the comforts. Sanitized. Mid-century modern and appointed to provide maximum functionality to relax. Fully stocked gourmet kitchen, full-size appliances; small ones too! Full-size bathroom: large walk-in shower with 2 shower head fixtures! Bidet & every amenity. Small private patio at rear with Adirondack chairs and bistro table to enjoy fresh air.
May 10 – 17
$297 CAD per night
4.99 out of 5 average rating, 157 reviews

Popular amenities for San Jose guesthouses

Family-friendly guesthouses

Guest favourite
Guesthouse in Sunnyvale
Private cottage in a garden
Jan. 23 – 30
$185 CAD per night
4.96 out of 5 average rating, 380 reviews
Superhost
Guesthouse in San Jose
1BR beautiful, cozy guest cottage in Willow Glen
Oct. 31 – Nov. 7
$201 CAD per night
4.84 out of 5 average rating, 207 reviews
Guest favourite
Guesthouse in Sunnyvale
Mid Century Modern Guesthouse
May 3 – 10
$218 CAD per night
4.95 out of 5 average rating, 355 reviews
Guest favourite
Guesthouse in San Jose
Private Studio Guesthouse with A/C in Willow Glen
May 6 – 13
$210 CAD per night
4.94 out of 5 average rating, 245 reviews
Guest favourite
Guesthouse in San Jose
Modern 2Bed/1Bath suite in San Jose
Jan. 31 – Feb. 7
$242 CAD per night
4.91 out of 5 average rating, 143 reviews
Guest favourite
Guesthouse in Los Altos
Splendid - Resort Style
Apr. 13 – 20
$289 CAD per night
4.98 out of 5 average rating, 366 reviews
Guest favourite
Guesthouse in Redwood City
Quiet , Private Studio / Cottage
Nov. 3 – 10
$177 CAD per night
4.98 out of 5 average rating, 371 reviews
Guest favourite
Guesthouse in San Jose
Gorgeous Casita(detached) in upscale neighborhood
Feb. 16 – 23
$190 CAD per night
4.91 out of 5 average rating, 117 reviews
Guest favourite
Guesthouse in Monte Sereno
Greenwood Guest House, a Peaceful Oasis
Nov. 10 – 17
$273 CAD per night
4.9 out of 5 average rating, 182 reviews
Guest favourite
Guesthouse in Half Moon Bay
Cabin on the coast near harbor & Surfer’s beach
Apr. 12 – 19
$219 CAD per night
4.82 out of 5 average rating, 419 reviews
Guest favourite
Guesthouse in Mountain View
Private studio in downtown
May 16 – 23
$206 CAD per night
4.96 out of 5 average rating, 257 reviews
Guest favourite
Guesthouse in Kensington
Secluded luxury cottage & hot tub
Jan. 21 – 28
$238 CAD per night
4.94 out of 5 average rating, 593 reviews

Guesthouses with a patio

Guest favourite
Guesthouse in Boulder Creek
Custom Tiny Home Retreat in the Redwoods
Apr. 6 – 13
$230 CAD per night
4.96 out of 5 average rating, 104 reviews
Guest favourite
Guesthouse in Woodside
SkyHigh Redwoods Retreat with Bay Views
Nov. 18 – 25
$297 CAD per night
4.96 out of 5 average rating, 135 reviews
Guest favourite
Guesthouse in Menlo Park
Charming, modern, restorative, private studio
Feb. 18 – 25
$171 CAD per night
4.95 out of 5 average rating, 148 reviews
Guest favourite
Guesthouse in Oakland
Guesthouse Garden Retreat
Apr. 15 – 22
$153 CAD per night
4.92 out of 5 average rating, 235 reviews
Guest favourite
Guesthouse in Half Moon Bay
Boho beach bungalow- walk to Poplar Beach
Jun. 26 – Jul. 3
$361 CAD per night
4.93 out of 5 average rating, 124 reviews
Guest favourite
Guesthouse in Boulder Creek
Digital Nomad Retreat
Jun. 10 – 17
$274 CAD per night
4.99 out of 5 average rating, 136 reviews
Guest favourite
Guesthouse in Berkeley
Berkeley Bitty House - a little bit of home
Jan. 25 – Feb. 1
$313 CAD per night
4.99 out of 5 average rating, 120 reviews
Superhost
Guesthouse in Oakland
NEW Adorable 1 bedroom guesthouse with Patio
Nov. 15 – 22
$133 CAD per night
4.87 out of 5 average rating, 135 reviews
Guest favourite
Guesthouse in Pleasant Hill
Charming Studio Guesthouse with Free Parking
May 1 – 8
$164 CAD per night
4.98 out of 5 average rating, 122 reviews
Guest favourite
Guesthouse in Mill Valley
Mill Valley Garden View Guest House, Free Parking
Jul. 30 – Aug. 6
$402 CAD per night
4.98 out of 5 average rating, 162 reviews
Guest favourite
Guesthouse in San Jose
Guest studio in Naglee Park
Jan. 19 – 26
$180 CAD per night
4.92 out of 5 average rating, 59 reviews
Guest favourite
Guesthouse in San Jose
Cozy Private Cottage near Japantown
Apr. 22 – 29
$188 CAD per night
4.96 out of 5 average rating, 71 reviews

Guesthouse rentals with a washer and dryer

Guest favourite
Guesthouse in San Jose
San Jose Guest Cottage
Mar. 26 – Apr. 2
$198 CAD per night
4.95 out of 5 average rating, 103 reviews
Guest favourite
Guesthouse in San Jose
Private Cottage nearby SCU/SanJoseDowntown/Airport
Sep. 1 – 8
$231 CAD per night
4.98 out of 5 average rating, 435 reviews
Guest favourite
Guesthouse in San Jose
Stylish standalone guesthouse near Santana Row
Dec. 8 – 15
$260 CAD per night
5.0 out of 5 average rating, 104 reviews
Guest favourite
Guesthouse in San Jose
Private cottage in the heart of Silicon Valley
Apr. 10 – 17
$245 CAD per night
4.98 out of 5 average rating, 238 reviews
Guest favourite
Guesthouse in San Jose
Evergreen Valley Hillside retreat
Oct. 4 – 11
$250 CAD per night
4.91 out of 5 average rating, 234 reviews
Guest favourite
Guesthouse in Campbell
Downtown Campbell Executive Cottage
Aug. 25 – Sep. 1
$268 CAD per night
4.99 out of 5 average rating, 264 reviews
Guest favourite
Guesthouse in San Jose
Private unit close to Santa Clara University
Sep. 7 – 14
$287 CAD per night
4.99 out of 5 average rating, 227 reviews
Guest favourite
Guesthouse in La Honda
Bicycle Shack @ La Honda Pottery
Dec. 15 – 22
$163 CAD per night
4.95 out of 5 average rating, 376 reviews
Guest favourite
Guesthouse in Santa Clara
New Construction Clean, Modern, Quiet Cottage
Aug. 19 – 26
$243 CAD per night
4.92 out of 5 average rating, 238 reviews
Superhost
Guesthouse in San Jose
Beautiful private guest house in downtown San Jose
Dec. 28 – Jan. 4
$149 CAD per night
4.78 out of 5 average rating, 405 reviews
Guest favourite
Guesthouse in San Jose
Lemon Tree Cottage, central silicon valley
Dec. 31 – Jan. 7
$267 CAD per night
4.96 out of 5 average rating, 186 reviews
Guest favourite
Guesthouse in Sunnyvale
Tranquil and Charming 1-Bedroom Guest house w/bath
Nov. 11 – 18
$158 CAD per night
4.89 out of 5 average rating, 161 reviews

Quick stats about guesthouse rentals in San Jose

Total rentals

370 properties

Rentals with dedicated workspaces

230 properties have a dedicated workspace

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

80 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

23K reviews

Destinations to explore