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Vacation rentals in Monte Sereno

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Top-rated vacation rentals in Monte Sereno

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

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Top guest favorite
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
4.96 out of 5 average rating, 137 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

Superhost
A hot tub is situated on a wooden deck surrounded by tall redwood trees, with sunlight streaming through the branches. Steps lead down to a shaded area, inviting relaxation in a serene natural setting.
Home in Boulder Creek
4.88 out of 5 average rating, 273 reviews

The Artists' Tree House

STVR permit #221203. This charming home is perched in the trees with views of the forest through the skylights. Close to the mountain town of Boulder Creek if you need groceries. We aim to give you the most comfortable stay and modern amenities. If you are a remote worker, we have a work space in each bedroom with a large monitor and desk. Dogs are welcome. Smoking outdoors is permitted. Located 35min to Santa Cruz, 1:30 to downtown SF and 45min to San Jose. Hot tub under the redwoods and relax!

Top guest favorite
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, 450 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.

Superhost
A charming outdoor patio area features a round table surrounded by four decorative chairs. Lush greenery decorates the space, including potted plants and foliage. Two turquoise doors are complemented by wall-mounted lanterns and classical sculptures, creating a peaceful setting for relaxation.
Guesthouse in Monte Sereno
4.84 out of 5 average rating, 166 reviews

Private Cozy Suite Los Gatos - Saratoga

This private suite with private entrance, bathroom,high speed internet & living room is the part of 1940's magical Mediterranean house. It is ideal for Silicon Valley corporate,entrepreneurs, business,travelers, couples, adventurers; artists and art lovers.Yet, walking distance to downtown Los Gatos'Monte Sereno restaurants, coffee shops, boutiques, local hikes close to Limekiln Trail & outdoor is around 15 minutes drive to/from San Jose airport and 45 minutes to/from San Francisco airport.

Guest favorite
A spacious studio features a large bed adorned with a red and white blanket, complemented by soft lighting from bedside lamps. A comfortable sofa with decorative pillows sits nearby, and large windows allow natural light to fill the room, enhancing its inviting ambiance.
Guesthouse in Campbell
4.78 out of 5 average rating, 153 reviews

Air Condition Cozy garden house.

A great studio in the Heart of Campbell, with walking distance to many restaurants and many boutiques in downtown Campbell. Only 12 min. to San Jose airport with out trafic. 20 min away from Levi Stadium and Six Flags Great America theme park. The famous Santana Row shopping and delicious restaurants is like a 7 min drive, and right by it we have one of the biggest malls of the bay area Westfield Valley Fair. We also have the Winchester mystery house museum across from Santana Row.

Top guest favorite
The image features a clear pool surrounded by a stone edge, with vibrant orange and purple flowers in bloom along the perimeter. Lush green palm trees and other landscaping elements provide a natural backdrop, creating a serene outdoor setting.
Guest suite in Cambrian
4.96 out of 5 average rating, 181 reviews

Private Queen Suite-Pool & Hot Tub, private entry

This is your World Cup spot! Enjoy your private suite, bathroom and large smart TV with all the action. Located within a mile of eBay & Netflix plus downtown Los Gatos and Campbell. Great forLevi's Stadium 9.5 miles, Mountain Winery Concerts 7.5 miles, San Jose International Airport 6.5 miles, SFO 35 miles, SAP Center 4.6 miles. We have a professional cleaning. Check-out like a hotel, no starting laundry! Hot tub and Pool are a perfect way to relax and end the evening.

Guest favorite
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, 823 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:)

Top guest favorite
A cozy cabin exterior is set among tall trees, featuring a stone patio with two Adirondack chairs. The structure has large windows that invite natural light, while the surrounding landscape includes rocks and pine needles, creating a natural and serene environment.
Cottage in Boulder Creek
4.98 out of 5 average rating, 130 reviews

Creekside Bliss #1 - The Santa Cruz

Santa Cruz County Vacation Rental Permit# 191283. Newly remolded beachy creek side cottage, bright and airy, fully equipped kitchen. Located in the Santa Cruz mountains 1/2 mile from downtown Boulder Creek on a secluded property. Close to many event and wedding venues. Fifteen minute drive to Big Basin State Park, 30 minutes to Santa Cruz and Beach Boardwalk, close to many wineries and lots of hiking trails. Twenty minutes from Roaring Camp Railroad.

Top guest favorite
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, 227 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.

Top guest favorite
A spacious bedroom features vaulted wooden ceilings and large glass sliding doors leading to an outdoor deck. A comfortable bed is flanked by two bedside tables with lamps. A decorative painting hangs above the bed, and a wooden dresser adds functional storage.
Guesthouse in Woodside
4.99 out of 5 average rating, 573 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

Guest favorite
The living area features a spacious gray sectional sofa with blue accent pillows, situated adjacent to a wooden coffee table. A patterned rug adds texture to the light wood flooring. Natural light fills the room from the window, which opens to the backyard.
Home in Cupertino
4.95 out of 5 average rating, 322 reviews

Newly rebuilt ultra clean designer home

Newly renovated ultra clean designer home in duplex minutes from Apple campus. Highly walkable, the entire home has been recently rebuilt from the studs with new top of the line designer furnishings, kitchen essentials, appliances, and toiletries. Disney+, Hulu, Cable TV, and Nespresso coffee included during stay with ultra-fast internet up to 500mbps. 5 min to Whole Foods 12 min to Apple Park 20 min to Stanford

Guest favorite
A spacious deck offers a panoramic view of fog-covered hills, with a golden sunset in the background. Multiple seating arrangements, including lounge chairs, are positioned for relaxation. An umbrella provides shade, while a table is set for dining outdoors.
Guesthouse in Saratoga
4.91 out of 5 average rating, 179 reviews

Newly Built Studio, 2000 FT Elevation with Jacuzzi

5 mins from Downtown Saratoga!! Its a great cozy spot to feel relaxed with a beautiful scenic view you will fall in love with featuring its own backyard seating area. This is a secondary detached unit that's fully equipped with everything your need such as full Bathroom and Kitchen, T.V, Wi-Fi, AC and Heater. **Ideal for Biking, Hiking or just simply taking in the beautiful sunset.

Popular amenities for Monte Sereno vacation rentals