
Guesthouse holiday rentals in Santa Cruz County
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Top-rated Guesthouses in Santa Cruz County
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

Mountain Retreat
Escape to the serene beauty of the Santa Cruz Mountains of Los Gatos! Our charming cottage rental is nestled amidst the towering redwoods, 30mins from Silicon Valley or Santa Cruz, and only 15mins from downtown LG, but feels isolated if you want get away from it all. The cottage features a living room (w/optional murphy bed) & full kitchen/dining area. Amenities like wifi, streaming and washing/dryer available in unit. Bedroom features king size bed and private backyard area. Pet friendly.

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. [Permit #: 181566] 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.

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.

Sunny Harborside Bungalow
Private small cozy 1 br/1ba bungalow. This space boasts a taste of Latin American beach, 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, turn on app notifications for communication.

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! IMPORTANT NOTE: I am required to collect the city mandated short term rental tax in cash when you arrive because the city of Santa Cruz . Please have it ready.

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!

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

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!

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!

Treescape, a perfect modern, rustic, SV getaway.
Welcome toTreescape Guest Suite, nestled in Scotts Valley finest neighborhoods, we’re located across the street, from beautiful Glenwood Preserve, & around the corner from 1440 Multiversity. Our remodeled guest suite is only a three-five minute drive, to local restaurants, grocery stores, coffee shops, microbrewery, and more. Treescape is 1 mile to HW-17, 8 miles to Santa Cruz, 10 miles to Natural Bridges State Beach, and 15 miles to Silicon Valley.

Light-Filled Redwood Cottage with Clawfoot Tub
Nestled beneath the redwoods, our peaceful guest house is designed to help you slow down, recharge, and reconnect with nature. Quiet, private, and surrounded by towering trees, it’s the perfect retreat for morning coffee on the porch, cozy evenings by the fire, and restful nights away from the noise of everyday life. (Permit 181242) Please note, this cottage is situated on a larger property that includes two other detached residences.

Cabana with Warm Watsu Pool
Our guests best describe it as: ‘Like luxury hotel meets Zen retreat meets Day Spa meets Bali rain forest meets mom and pop warm hospitality’. A private cabana close to shops and restaurants in downtown Willow Glen. You’ll love our place because of the tranquil setting, warm watsu pool, Finlandia sauna, hot plunge, and beautiful gardens. Our place is good for couples, solo adventurers, and business travelers.
Popular amenities for Santa Cruz County guesthouses
Family-Friendly guesthouses

Quiet Poolside Cottage for Solitude

cute cottage walking distance to beach

Rustic Cottage, Redwoods, Beaches.

Luxe Suite with Private Yard & AC

Newly Built Studio, 2000 FT Elevation with Jacuzzi

Redwood Retreat

Sunny Garden Guesthouse on the Westside

SC Boat Harbor/Boardwalk Hideaway
Guesthouses with a patio

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

The Point Cottage

New 2 story modern 2bd/1 ba in a quiet cul-de-sac

Orchard Cottage in convenient countryside location

Creekside Santa Cruz Mtns Hot Tub Cabin Pet+

Natural Bridges Beachside Retreat w/ Views

Little Tuscany in Morgan Hill, CA

D’s Garden Cottage
Guest house rentals with a washing machine and dryer

Bright ADU w Private Entrance & Yard

Los Gatos/Cambrian COTTAGE-HOT TUB/pvt.parking

Newly Built | Modern 1BR/1BA Private Cottage

Greenwood Guest House, a Peaceful Oasis

Private Entry Adorable 1 bed 1 bath

Cozy 1-Bedroom duplex in Seabright

Modern 2Bed/1Bath suite in San Jose

Victorian Cottage on West Cliff Drive 18-0089
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- Stanford University
- Monterey Bay Aquarium
- Santa Cruz Beach
- Capitola Beach
- Santa Cruz Beach Boardwalk
- Carmel Beach
- Levi's Stadium
- SAP Center
- Henry Cowell Redwoods State Park
- Rio Del Mar Beach
- Carmel Beach
- Seacliff State Beach
- California’S Great America
- Montara Beach
- Gilroy Gardens Family Theme Park
- Pebble Beach Golf Links
- Winchester Mystery House
- Asilomar State Beach
- Big Basin Redwoods State Park
- Natural Bridges State Beach
- Manresa Main State Beach
- Pacifica State Beach
- Googleplex
- Twin Lakes State Beach
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