Guesthouse vacation rentals in Los Gatos

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Top-rated guesthouse rentals in Los Gatos

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 7 – 14

G$32,992 GYD 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 7 – 14

G$31,239 GYD per night

Guest favorite

Guesthouse in San Jose

4.96 out of 5 average rating, 190 reviews

Lemon Tree Cottage, central silicon valley

Private cottage, sky-lit upbeat decor, 2 laptop workspaces, lots of opportunity for relaxation. Fully equipped kitchen includes water purifier, dining area opening onto patio and garden, satellite TV. Master BR w/ queen bed, private patio. 2nd BR w/ queen bed, view of water feature. Bathroom w/ custom tile, shower, and laundry. Attention to detail and professional cleaning makes for an extra comfortable and safe stay. The cottage is not set up to accommodate infants/small children.

Jan 10 – 17

G$34,675 GYD 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 21 – 28

G$31,785 GYD per night

Guest favorite

Guesthouse in Los Gatos

4.91 out of 5 average rating, 312 reviews

Los Gatos/Cambrian COTTAGE-HOTTUB/ pvt.parking

This private entrance guest house is nestled in back of the property. detached behind main home. Private enclosed patio and 1 park spot. *We take all cleaning precautions Studio has 1 Queen bed(additional cot for 3rd guest, or guest wanting to add cot)* host must have prior notice. We welcome your well behaved pets… All DOGS ON PROPERTY(including service dogs MUST HAVE prior consent from host-( provide Current/up-to-date vaxs for disease prevention (rabies,dh2pp, bordatella, leptospirosis)

Jul 6 – 13

G$30,683 GYD per night

Guest favorite

Guesthouse in Los Gatos

4.82 out of 5 average rating, 549 reviews

Rustic Cottage, Redwoods, Beaches.

Tiny, quaint Cottage sequestered in a Redwood forest. Outdoor Claw foot Bathtub with Shower under the Stars overlooking a Spring fed creek ! Mature Pond with sitting areas with Koi and Turtles ! Solar powered lights at night will amaze you ! Lighting at the Cottage is Solar powered and some Battery powered Lanterns are provided ! There is a Cell Phone & device Charging Station available . No Kitchen or cooking facilities . Summit Market four miles away , open 7 days a week / hours are 8-8

Jul 26 – Aug 2

G$20,965 GYD per night

Guest favorite

Guesthouse in Los Gatos

4.94 out of 5 average rating, 194 reviews

Private Garden Cottage with Private Entrance

Discretely nestled at the rear of the property; affording ample privacy. Bamboo floors, a comfy king size bed, designer bathroom, large closet, television & kitchenette equipped with coffee maker, microwave and mini fridge. Located in a quiet, safe neighborhood at the end of a cul-de-sac. Close to quaint, downtown Los Gatos; known for its fine restaurants, coffee houses, pubs, shops, salons, spas, unique boutiques and an Apple store. 15 minutes to SJC Airport and 20 miles to the beach.

Jan 13 – 20

G$32,981 GYD 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!

Jun 16 – 23

G$48,276 GYD per night

Guest favorite

Guesthouse in Monte Sereno

4.9 out of 5 average rating, 187 reviews

Greenwood Guest House, a Peaceful Oasis

Welcome to Greenwood Guest House, a 1 bedroom, 1 bath private house situated in a peaceful and expansive backyard with a pool, tennis court, and beautiful scenery. Our space is a good fit for business trips, couple vacations, and family visits. The kitchenette and laundry room make longer stays quite enjoyable. Easy access to Highway 17 and 85, 15 minute drive to San Jose airport (SJC) and 2 minute drives to either downtown Los Gatos or Saratoga.

Apr 19 – 26

G$38,525 GYD per night

Guest favorite

Guesthouse in Willow Glen

4.97 out of 5 average rating, 571 reviews

Cabana with Warm Watsu Pool

Our guests best describe it as: ‘Like luxury hotel meets Zen retreat meets Day Spa meets Bali rain forest meets mom and pop warm hospitality’. A private cabana close to shops and restaurants in downtown Willow Glen. You’ll love our place because of the tranquil setting, warm watsu pool, Finlandia sauna (currently open), hot plunge, and beautiful gardens. Our place is good for couples, solo adventurers, and business travelers.

Jul 25 – Aug 1

G$42,579 GYD per night

Guest favorite

Guesthouse in Boulder Creek

4.94 out of 5 average rating, 108 reviews

BC Treehouse

We are nestled up among the Oak Trees and Redwood and are less then 1 mile from Historic downtown Boulder Creek. 25 minutes to Santa Cruz and the Beach Boardwalk. Henry Cowell Redwoods State Park and Roaring Camp Railroads are 15 minutes away. 35 minutes to Davenport and Wilder Ranch State Park. Lots of areas for river play for the kids within 15 minutes. Epic mountain biking and hiking surrounds you. .

Jan 1 – 8

G$30,479 GYD per night

Guest favorite

Guesthouse in San Jose

4.98 out of 5 average rating, 248 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.

Oct 2 – 9

G$33,162 GYD per night