Guesthouse holiday rentals in Santa Cruz

Guesthouse in Monte Sereno

4.98 out of 5 average rating, 445 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.

4.98 out of 5 average rating, 134 reviews

Carriage House on West Cliff Drive 18-0090

Historic stand-alone Victorian carriage house on the grounds of oceanfront home, Epworth-by-the-sea. Fully furnished. Gas heating stove, well-stocked gourmet kitchen, comfortable bedroom, luxurious and opulent bathroom. Perfect for a romantic getaway, or for extended stays. Free WiFi, parking, cable. Pet friendly (additional fee applies) and well located to enjoy all that Santa Cruz has to offer. Posted rates include mandated SC Hotel Tax, NOT charged for stays longer than 30 nights.

4.8 out of 5 average rating, 787 reviews

Guesthouse in Aptos

The Cottage Getaway by the Sea

The Cottage Getaway by the Sea is a single level one bedroom stand alone cottage on a cliff over Rio Del Mar Beach w/ 180 degree WOW views of the Monterey Bay. Seasonally enjoy dolphins, whales, & great sunsets! Located in a peaceful neighborhood, this is a perfect place for a quiet romantic getaway or just to read, relax, & enjoy. We are one of the few airbnbs with a California King Bed! Pricing is per night for one; 2nd person +$25 per nite PERMITTED vacation rental #181420

4.96 out of 5 average rating, 205 reviews

Guesthouse in Felton

Felton Forest Cottage Near Henry Cowell State Park

Your new weekend retreat! The Cottage is situated on unique forest-farm acreage across the street from Henry Cowell Redwoods State Park, surrounded by redwood fairy circles and a beautiful stream. Charming, private, and yet handily walkable/drivable to parks surrounding the town of Felton and the Santa Cruz Mountain area. About 1 hour south of San Francisco, we're a quick 14 minute drive down picturesque Highway 9 to downtown Santa Cruz and it's popular beaches and Boardwalk.

Guesthouse in Scotts Valley

4.91 out of 5 average rating, 173 reviews

The Hen House Haven

Welcome to The Hen House Haven, a charming retreat where comfort meets modern amenities. Enjoy fresh eggs from our ten friendly hens, though egg availability may vary, especially in winter. Located near the Santa Cruz Beach Boardwalk, Henry Cowell Redwoods, and scenic hiking trails, our cozy studio is perfect for a relaxing getaway or adventure-filled stay. Embrace the serenity and warmth of staying with us, and make yourself at home. We can't wait to host you!

Guesthouse in Almaden Valley

4.97 out of 5 average rating, 998 reviews

Cabana in Sierra Azul Open Space Preserve

Nestled in the Sierra Azul Mountain Range in Los Gatos, we enjoy AMAZING unobstructed views of the Entire Silicon Valley... San Francisco to Gilroy from 1700ft altitude! This private retreat is perfect for relaxing and rejuvenating, surrounded by forest, streams and wildlife! Relax in complete solitude, refresh with chemical-free, great tasting spring water and crisp clean air high above the smog of Silicon Valley! Great Hiking/Biking Trails at your backdoor!

Guesthouse in Upper Seabright

4.91 out of 5 average rating, 707 reviews

Sunny Harborside Bungalow

Private small cozy 1 br/1ba bungalow. This space boasts a taste of Latin American beach, Spanish tile floors and wood furniture. Kitchenette with an induction burner and xl toaster oven (no range) , full size fridge, private patio seating, umbrella, tropical plants. Bathroom with a small shower. Curtained off bedroom with full closet, queen bed. Living room has day bed/couch with twin mattress for 3rd guest. Plz read “other details to note” before booking.

Guesthouse in Portola Valley

4.94 out of 5 average rating, 208 reviews

Woodsy Silicon Valley Cottage

Discover a laid-back side of Silicon Valley in a cozy, cedar-shake guesthouse surrounded by mature trees. Walking distance from a great network of destination hiking and biking trails. 15-30 minutes from Stanford, Sand Hill Road, and major tech companies. This 400 square foot space is on top of our garage and next to our home. There is no public transportation nearby and ride share services are available but not always reliable so you'll need a car.

4.89 out of 5 average rating, 641 reviews

Santa Cruz Guesthouse Surrounded by Redwoods

Get back in touch with nature in a farmhouse-style property next to abundant woodlands and hiking trails (Permit 181242). It's an airy, skylit space with honey-colored hardwood floors and a well-equipped kitchen. Bathe in a claw-foot tub and relax on a wooden porch. Please note that this house shares the property with the owners who live in the main house, and an Airstream. The property is also serviced by landscapers and pest services.

4.93 out of 5 average rating, 736 reviews

Cozy garden westside king suite STR18-0122

This cool and comfortable private space is a great spot to stay while visiting Santa Cruz. Close to everything yet private with its own private entrance and in a quiet setting with an outdoor sitting area. The neighborhood is old Santa Cruz and close to everything. Don’t forget the comfortable king bed! The best deal in Santa Cruz! MAKE SURE TO READ IMPORTANT NOTE!

Guesthouse in Scotts Valley

4.9 out of 5 average rating, 130 reviews

The Hideaway: Sunny 2BR Apartment in the Redwoods

Welcome to our spacious 2-bedroom, 1-bath apartment in the heart of the Redwoods! With towering trees all around, you'll feel like you're truly escaping into nature. Enjoy the beautiful scenery and fresh air from the comfort of your own oversized deck, complete with an outdoor dining table and umbrella with lights - perfect for relaxing after a day of exploring.