Guesthouse holiday rentals in Santa Cruz

4.99 out of 5 average rating, 736 reviews

Guesthouse in San Carlos

Private Garden Cottage

Relax in our cozy cottage nestled in a serene garden setting, the perfect get-away after a day of business meetings or sightseeing. We are close to major Silicon Valley destinations; 30 minutes from San Francisco, San Jose and the beach in Half Moon Bay —with easy access to Highways 101 and 280, as well as public transportation (SamTrans, Caltrain and BART via Caltrain). Our quiet street is an easy 5-minute walk (0.2 mi) from downtown San Carlos with shops and literally dozens of restaurants.

Guesthouse in Boulder Creek

4.98 out of 5 average rating, 234 reviews

Digital Nomad Retreat

Imagine yourself in the REDWOOD FOREST and take a breath of mountain air. Only 25 miles from the Silicon Valley, 15 miles from the Santa Cruz Boardwalk, a cozy location tucked in the forest. Many are on the move and can work from anywhere, so why not a beautiful place of your own? A perfect getaway spot central to WINE TASTING, HIKING, BEACHES and even mountain exploration, right from the doorstep. Located only a mile and a half from downtown Boulder Creek, food and window shopping are easy.

4.85 out of 5 average rating, 248 reviews

Guesthouse in Felton

Studio with redwoods in backyard, infrared sauna

Deer Run sanctuary nestled in the redwoods, with bubbling brook nearby. private and secluded yet walking distance to felton's town center restaurants and shoppings. Five minute walk to Henry Cowell State Park and a short 6 mile drive to Santa Cruz's beaches and downtown. The studio is attached to the owner residence but has a private entrance, kitchenette, bathroom and gas fireplace. Deck surrounded by redwoods, is partitioned for privacy. Studio is good for couples and solo travelers.

4.99 out of 5 average rating, 321 reviews

Charming Light-Filled Carriage House Apartment

Our 1928 carriage house apartment is walking distance to the Boardwalk, beach, wharf, basketball stadium, and downtown. Cowells and Main Beaches, Steamers Lane, Boardwalk, wharf, and West Cliff Drive (path along the ocean) are all a quick 5 min walk from our house. The apartment is located in a private garden setting, away from the main street, behind our home. There is a separate dedicated garden space for you to use. We hope you will love this historical neighborhood as much as we do!

4.79 out of 5 average rating, 775 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

4.97 out of 5 average rating, 285 reviews

Guesthouse in Woodside

SkyHigh Redwoods Retreat with Bay Views

Inhale. Exhale. Relax in this cozy, romantic guesthouse retreat nestled in the redwoods of the Santa Cruz Mountains, overlooking the bay and conveniently located near the famous Alice’s Restaurant on Skyline Blvd in Woodside. The 1 acre gated property has ample parking and privacy. Snuggle in with the wood burning fireplace, prepare meals in the full size kitchen and take in the views of the majestic redwoods right outside the windows with bay views peeking through the trees.

Guesthouse in Scotts Valley

4.92 out of 5 average rating, 155 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, 981 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!

4.9 out of 5 average rating, 697 reviews

Guesthouse in Seabright

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.

Superhost

4.89 out of 5 average rating, 627 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.

4.94 out of 5 average rating, 724 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!