Holiday houses in Monte Sereno

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Top-rated holiday rentals in Monte Sereno

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

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Top Guest favourite

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

4.97 out of 5 average rating, 184 reviews

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

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Guest favourite

A newly constructed home is depicted with a modern design, featuring a gray roof and large windows. The driveway is paved with stone, leading to a garage door. Surrounding the house, an array of colorful flowers and landscaping elements enhance the outdoor environment.

Guest suite in Monte Sereno

4.94 out of 5 average rating, 35 reviews

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.

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Top Guest favourite

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.

Guesthouse in Los Gatos

4.98 out of 5 average rating, 124 reviews

Oak&Bloom cottage - Los Gatos, 2 bedrooms, 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.

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Top Guest favourite

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.

Guesthouse in Monte Sereno

4.98 out of 5 average rating, 464 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.

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Guest favourite

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

4.9 out of 5 average rating, 104 reviews

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!

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Top Guest favourite

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.

Guesthouse in Monte Sereno

4.99 out of 5 average rating, 88 reviews

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.

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Top Guest favourite

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

4.9 out of 5 average rating, 863 reviews

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:)

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Top Guest favourite

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.

Guesthouse in Monte Sereno

4.91 out of 5 average rating, 238 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.

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Top Guest favourite

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.

Guesthouse in Los Gatos

4.99 out of 5 average rating, 621 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!

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Guest favourite

A cozy sleeping area features a queen bed adorned with a patterned duvet cover. Natural light filters through a large window framed by curtains, illuminating a decorative wall piece nearby. A bedside lamp rests on a side table, complementing the minimalist design.

Guest suite in Los Gatos

4.87 out of 5 average rating, 150 reviews

Modern studio in charming Los Gatos,Silicon Valley

It is a guest studio with an independent private entrance in a newly built home in quiet residential neighborhood in Los Gatos, CA. The studio can comfortably host up to 2 adults. The studio is close to Santa Cruz mountains with world class wineries, state parks and beaches. It is also in the heart of Silicon Valley, a few miles away from offices of Netflix, Apple etc. We are 15 mins away from SJC airport and 40 mins from SFO airport.

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Guest favourite

Guesthouse in Campbell

4.88 out of 5 average rating, 271 reviews

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.

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Guest favourite

A spacious living area features a dark sectional sofa and a wooden coffee table adorned with a plant. A modern fireplace is positioned against a light wall. Behind, sliding glass doors lead to an outdoor patio, with a dining table set for four beside them.

Townhouse in Los Gatos

4.91 out of 5 average rating, 140 reviews

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.

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