Guest house holiday rentals in Santa Cruz

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.

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

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.

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!

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.

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.

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.

Modern Cottage in Santa Cruz

Adventure awaits you here in Santa Cruz! Whether you’re coming to enjoy the hiking of nearby Henry Cowell Redwoods State Park or heading down to Pleasure Point for a surf, we’re close to it all! Here you’ll find the perfect place to get some R&R after a busy, adventure filled day. Keep it simple at this peaceful and centrally-located spot.

Timeless Coastal Carriage House

Central location on historic steam train line in downtown Santa Cruz. Walk to beaches, surfing, the Boardwalk & Pier, museums, restaurants, nightlife, bike paths, spas, yoga & UCSC. Comfortable, private apartment admist whimsical Victorians and manicured gardens. Enjoy the best of Santa Cruz!