Vacation rentals with outdoor seating 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

Eclectic Escape

The perfect stay for adventure seekers and relaxation enthusiasts. (Permit 251052) Unwind with yard games and bbq, soak up the sun from the deck or relax in a hammock under redwood shade. Cozy up on a comfy couch, enjoy forest views through skylights, or watch movies on the big screen. Explore hiking trails just steps away, vast mountain biking trails (10 min), or hit the beach and surf (13 min). Indulge in wine tasting at a local mountain vineyard nestled amongst the redwood giants (5 mins).

Cozy Coastal Redwood Cabin

Rest and connect in this warm, cozy, and private cabin that is nestled in the redwoods. Only minutes away from Henry Cowell State Park, where you can enjoy world class mountain biking trails, hiking, or swimming in the river. Or, enjoy the beach 15 minutes away. This is a perfect place to refresh in the magic of the Coastal Redwoods. Music fills most nights either from the Felton Music Hall or from the chorus of frogs. And wake up in the mornings to the mist in the trees when the fog rolls in.

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.

Luxury Silicon Valley Wellness and Work Oasis

Ideal for guests attending matches at Levi’s Stadium, business travelers, couples, and nature lovers, while staying in a quiet residential setting. Peaceful upscale exclusive use 1,500 sq ft Los Altos Hills retreat beside Rancho San Antonio Preserve. Private trail access. Fast fiber Wi-Fi, workspace, fireplace, sauna, pool table, full kitchen, plush queen bed. Year-round hot tub, BBQ patio, saline pool. Minutes to Stanford, Los Altos, Palo Alto, and major tech campuses, dining and shops.

Five Star Smart Home Living Experience

SUPER BOWL CLOSE LOCATION!! Nestled beneath a century old oak tree and only a 5-10 minute walk to downtown Los Gatos or Vasona Park sits a newly constructed 900 square foot 1 BR, 1.5 bath loft style luxury townhome with a private front entrance and backyard. This exclusive experience in downtown Los Gatos is ideal for someone (or a couple) looking for the comfort, quiet and privacy of a detached home in the center of one of the San Francisco Bay Area’s most desirable communities.

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

Beautifully remodeled, sparkling clean, and cozy 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.

Redwood Cottage & Hot Tub

Enjoy this peaceful redwood retreat tucked away in the Santa Cruz Mountains. This small private cottage comes with a private hot tub, outdoor shower, propane fire pit and hammock. You'll be 10 minutes to downtown Felton and 25 minutes to Santa Cruz. The cottage is on a shared property and next door to the main house. Please note there is no indoor shower (outdoor only). Although 4 wheel is needed, THE ROAD IS RURAL, NARROW AND STEEP. Ideal for confident drivers. Permit #211304

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:)

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.

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.

Orchard Cottage in convenient countryside location

Orchard Cottage is a newly refurbished historical home in a rural neighborhood 10 minutes from downtown Los Gatos. Lots of wildlife and beautiful scenery make this location in the Santa Cruz Mountains a peaceful retreat from city life. Enjoy your private deck and yard or visit our ducks for a mini-farm experience. Lots of nearby hiking and wineries, and only 25 minutes to Santa Cruz beaches. Please contact me with any questions!