Vacation rentals in Monte Sereno

4.96 out of 5 average rating, 190 reviews

An A-Frame cabin is surrounded by lush greenery, positioned on elevated ground. A stone pathway leads to the entrance, flanked by wooden railings. The cabin features large glass panels on its façade, allowing natural light to flood the interior. A deck with seating overlooks the nature surroundings.

Cabin in Felton

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

A private stone patio is adorned with wooden chairs, overlooking a garden filled with plants. The sunset illuminates the sky with soft hues of pink and orange, creating a serene backdrop against the rolling hills and trees.

4.98 out of 5 average rating, 126 reviews

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

Escape to a spacious, beautifully remodeled and impeccably clean two-bedroom cottage in a desirable neighborhood, with sweeping canyon and mountain views less than two miles from downtown Los Gatos. Enjoy California living in a tranquil private yard with lush landscaping and multiple seating areas. Inside, you'll find a fully equipped kitchen, Nespresso coffee, high-speed internet, air conditioning and comfortable living spaces. Guests consistently love their stay, as reflected in our reviews.

4.92 out of 5 average rating, 101 reviews

A cozy living area is furnished with two red leather sofas and a single armchair. A television is mounted above a light wood cabinet. Soft blue area rugs cover the floor, and a large artwork of a horse adorns the wall, with natural light filtering through sheer curtains.

Guest suite in Los Gatos

Entire In-Law Unit at Ridge Ranch

Whether you are here for vacation or business you will enjoy this newly remodeled, private in-law unit in an affluent, countryside neighborhood. Comfortable beds and high quality linens. Original art by R. Apple of our horses. Surrounded by mountains, redwoods with private trails, and a horse pasture. Only 10 min to dining and entertainment in Los Gatos, 20 min to Santa Cruz and an hour to San Francisco. Access to large network of trails for hiking and biking. One pet welcome. Max four guests.

Guesthouse in Monte Sereno

The cottage exterior features a charming design with a slate stone patio and a round dining table with two chairs. Glass double doors provide access, and large windows offer views of the surrounding greenery. The roof is intricately shaped, complementing the natural setting.

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.

4.98 out of 5 average rating, 464 reviews

4.95 out of 5 average rating, 128 reviews

A modern workspace is highlighted by a wooden desk and clear chair, accompanied by a lamp. A wall-mounted television displays an ocean scene. A kitchenette with a microwave and mini-fridge is visible, while a bathroom area with a sink and mirrors is seen in the background.

Guesthouse in San Jose

Luxe Suite with Private Yard & AC

Perfect for solo travelers or those with pets, this centrally located San Jose suite combines luxury and comfort. Sleep like royalty on a queen bed, start your day with a Nespresso, and enjoy a mini-fridge, microwave, and 45" TV at your workspace. Indulge in premium toiletries, AC, and use the hair dryer and steamer for a polished look. Easy self-check-in/out. The trendy wood panel wall adds style, creating your private cocoon. Plus, enjoy a private yard to relax and feel the outdoor breeze.

4.91 out of 5 average rating, 108 reviews

An enchanting treehouse is nestled among the branches, adorned with warm string lights against a twilight sky. Adjacent, a living area features a large smart TV mounted on the wall above an electric fireplace, creating a cozy focal point.

Tiny home in San Jose

Family Favorite: Mickey Dream Loft & TREE house

Welcome to your next unforgettable stay — where comfort meets adventure in a space designed for fun-loving families and couples. 🌟 🧗‍♂️ Sleeping lofts accessed by indoor ladders — best suited for physically agile, adventurous guests 🌳 Relax in a magical backyard featuring a real treehouse, firepit & BBQ 🛁 Unwind in a spa-style bathroom with luxe touches 👨‍🍳 Cook like home in a fully stocked kitchen 🎮 Enjoy games, 65” TVs, and flexible workspaces 🌟 Discover More Below!

Guesthouse in Monte Sereno

A vibrant garden area is filled with various potted plants in colorful containers, featuring blooming flowers in shades of pink and white. A stone staircase leads to an inviting cottage entrance, surrounded by lush greenery and decorative items that enhance the serene environment.

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.

4.99 out of 5 average rating, 89 reviews

4.9 out of 5 average rating, 867 reviews

A charming cottage exterior is framed by tall cacti and vibrant flower gardens. A welcoming white door with a seasonal wreath invites guests inside. To the side, red chairs provide a cozy seating area, accompanied by a small table, amidst lush greenery.

Guest suite in Los Gatos

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:)

Guesthouse in Monte Sereno

A vibrant garden is showcased, featuring blooming red flowers and lush green plants. A stone patio leads to a tranquil blue pool, framed by greenery and distant hills. Decorative pottery is placed among the flora, adding charm to the natural setting.

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.

4.91 out of 5 average rating, 239 reviews

Superhost

An open living space features a light-colored sofa adorned with colorful cushions, complemented by a plush area rug. A wall-mounted television is positioned opposite the seating. Natural light filters through sheer curtains, illuminating the room with a view of the private yard through glass doors.

4.88 out of 5 average rating, 136 reviews

Los Gatos Cozy 2BD 2BA Private Guesthouse

Enjoy a peaceful stay in this brand-new guesthouse in Los Gatos. Nestled in a safe, tranquil, upscale neighborhood. Private side yard, assigned parking, separate entrance. Open-concept living area, spacious bedrooms, and full kitchen. Exterior security cameras and systems. 20 min to SJ Airport, 6 min to Netflix, 6 min to Downtown Los Gatos, <5 min to Vasona Park, 3 min to Good Samaritan Hospital, 25 min to Stanford Hospital, 3 min to Whole Foods

The spacious interior features rustic wooden walls and exposed beams. A cozy bed with plush bedding is highlighted by warm lighting. A comfortable seating area is nearby, along with a large round mirror and a modern flat-screen TV on the wall.

4.99 out of 5 average rating, 623 reviews

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!

A cozy living area features two leather sofas positioned around a rustic coffee table. Natural light filters through large windows, illuminating the space. A rocking chair adds a touch of charm beside an accent lamp, and a soft area rug adds warmth to the flooring.