Vacation rentals in Monte Sereno

Santa Cruz A-Frame

This unique A-Frame cabin, in a quiet mountain neighborhood with private creek access, was handbuilt in 1965 and remodeled in the summer of 2024. Now a little slice of heaven on the creek in the redwoods. *5-10 min to Henry Cowell Redwoods State Park, Roaring Camp Railroad, Loch Lomond Recreation Area, the Trout Farm Inn, Quail Hollow Ranch + Felton stores. *20 min to Santa Cruz, beach + Boardwalk. *1 min to Zayante Creek Market (EV charger) Find us on social: Insta @SantaCruzAFrame

Family · Location · Check-in

New, Luxury, w/ garage near Netflix & downtown LG.

Experience unparalleled privacy in this 7 year New, studio guest home w/ 9 ft high ceilings, surrounded by beautiful gardens nestled in the prestigious Monte Sereno. This luxury retreat offers a seamless "turn-key" lifestyle just minutes from Netflix, silicon Valley & downtown Los Gatos. Private entrance & an attached, one-car garage w/ epoxy flooring & ample storage. Full size contemporary european Kitchen, Full bath & huge shower. All utilities, washer, dryer, cable, furnishings are included.

Location · Value · Accuracy

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.

Location · Family · View

Oak&Bloom cottage - Los Gatos, 2 bedroom, private

Beautifully remodeled, sparkling clean, air-conditioned, private two-bedroom cottage with sweeping canyon and mountain views, located less than 2 miles from charming Downtown Los Gatos. Enjoy mornings with Nespresso coffee in the peaceful private yard, explore nearby parks, and access scenic hiking and biking trails just minutes away. Inside, the cottage offers a fully equipped kitchen, air conditioning in every room, and fast fiber internet. Santa Cruz Beach is a scenic 30-minute drive.

Location · Value · Parks

An Adventurer's Private Cottage Paradise

*Any stay 30+ days requires a background check(50$), a signed lease and a strong and consistent positive review history. Wifi speeds: 67 Mbps download, 11 Mbps upload. You don't have to be named Indiana Jones to enjoy the Far East touches of this private and fun studio and bath. Everything is provided: a work space, a cooking/eating place, and even an outdoor space with BBQ. Whether you are traveling for work or play, this cottage will make your stay more fun and memorable!

Family · Location · Layout

D’s Garden Cottage

Our charming 500 sq ft English cottage nestled within a beautiful garden offers a serene escape for those seeking tranquility and relaxation with a pool area and garden you can relax in. Inside, our cozy cottage awaits, adorned with rustic charm and modern comforts. The open-plan living area has king size bed and a 40" TV with a comfortable large couch, and a spacious bathroom. Come experience D's Garden Cottage—it's more than a place to stay; it's a destination to remember.

Location · Family · Backyard

Charming Hidden Cottage

A home away from home, this hidden little gem is a great getaway from the hustle and bustle of the cities. Still located conveniently close to businesses of all kinds including multiple down town areas, HWY 17 and 85, 1 mile from Netflix. We are constantly working on our cottage style gardens, so there will always be gardens to enjoy for you. If you are interested in trying any of our homegrown veggies or fruits just let us know, we love sharing our bounty:)

Location · Value · Quiet

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.

Value · Family · TV

Sanctuary in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, the Sanctuary combines rustic country decor, original art and spa amenities, 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!

Location · Value · Sleep quality

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.

Family · Value · Breakfast

Private Entry Studio with parking

This private entrance guest house on the property is isolated away from the large house free of contact with others. Five minutes from good Samaritan Hospital and ten minutes from Kaiser Permanente Hospital. Family neighborhood, close to freeway access to Santa Cruz San Jose or San Francisco. 15 min drive to Apple, 24 min to google. Perfect for a professional trip or just visiting.

Location · Family · TV

Entire stylish townhome-Los Gatos, great location

You will be close to everything Silicon Valley has to offer. This home is equipped with everything to make your experience feel like your home away from home. From here, you are only a short walk or drive to Vasona Park, downtown Los Gatos, amazing restaurants/wineries, endless hiking trails, and easy access to anywhere you would like to go in the Bay Area.

Value · Location · Quiet