Guesthouse holiday rentals in Monterey Bay

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Top-rated Guesthouses in Monterey Bay

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Los Gatos

4.92 out of 5 average rating, 360 reviews

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

This charming cottage, located on the outskirts of Los Gatos in the quiet and safe Cambrian neighborhood, is an ideal retreat away from the busy downtown. We ensure a safe and comfortable stay with rigorous cleaning protocols. The studio features one queen bed, with an additional cot available upon request. Please note that dogs are on the property. All dogs, including service dogs, must have prior consent from the host and provide current vaccinations (rabies, DH2PP, bordetella, leptospiros.

Top Guest favourite

Guesthouse in Boulder Creek

4.99 out of 5 average rating, 220 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.

Top Guest favourite

Guesthouse in Santa Cruz

4.98 out of 5 average rating, 131 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.

Guest favourite

Guesthouse in Seaside

4.91 out of 5 average rating, 736 reviews

Sunny Seaside Bungalow with Ocean View & Two Decks

Close to The Monterey Bay Aquarium , art and culture, restaurants and dining and the beach. You’ll love my place because it's a detached new unit, clean and on the Monterey Peninsula. My place is good for couples, solo adventurers, business travelers, families with kids, and pets (Dogs only please). We consider Dogs to be part of the Family so If you would like to bring your dog (2 max), please add them as a guest. That will cover the added expense in the cleaning of the Bungalow.

Top Guest favourite

Guesthouse in Woodside

4.97 out of 5 average rating, 259 reviews

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.

Top Guest favourite

Guesthouse in Scotts Valley

4.97 out of 5 average rating, 117 reviews

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.

Guest favourite

Guesthouse in Moss Landing

4.96 out of 5 average rating, 210 reviews

Private and peaceful beach cottage

Standalone studio steps from the beach! Private & gated guests only parking - Across the street from the Moss Landing harbor and KOA park - Home to Teco & Valentina, the resident barn owls. Owls are known to put on quite a show! They are super cool & beautiful! Watch them in their owl box from the live feed on our website/YouTube! Located on same property as The Haute Enchilada Cafe & Gallery. Visit us at hauteenchilada.com for lunch reservations!

Top Guest favourite

Guesthouse in Woodside

4.99 out of 5 average rating, 538 reviews

Guest House in the Woods

Our guest house is located close to La Honda and Woodside in the North Santa Cruz Mountains. Located in the Redwood forest and looks down onto a beautiful creek from a lovely deck. There are many open space hiking and biking trails within a short drive, and the beach. 5 miles from Alice's Resturant. San Francisco and Santa Cruz are easily accessible. The house has vaulted ceilings and a full kitchen, and laundry.

Superhost

Guesthouse in San Jose

4.78 out of 5 average rating, 483 reviews

Beautiful private guest house in downtown San Jose

Our guest house is located in downtown San Jose walking distance to Downtown San Jose, SJSU, Convention Center, Silicon Valley tech companies. It is behind the main house and has been fully renovated as has the entire property. Easy access to the private with everything you need to relax and vacation, or business travel. All around Public transportation like Light rail and Buses.

Guest favourite

Guesthouse in Gilroy

4.89 out of 5 average rating, 410 reviews

Back-to-Eden Guest House on a Farm

Peaceful, comfortable guest house with 3 bedrooms and 2 baths plus spacious living room. Fresh country air, quiet surroundings, beautiful sunrise and sunset. 8-10 people max. Any larger group will need prior arrangement with the host. Super fun animal interaction tour may be available during your stay . Please inquire upon booking regarding joining a tour.

Superhost

Guesthouse in Carmel Valley

4.94 out of 5 average rating, 245 reviews

Guest House in Sunny Carmel Valley

In Carmel Valley, just east of the famous Bernardus Spa and vineyard, this luxurious, fully equipped guest house is an ideal choice for a romantic getaway or a longer stay for one of the Monterey Peninsula's great events. Privacy, beautiful gardens and wine country atmosphere all conspire to make this getaway a place to recharge and relax.

Superhost

Guesthouse in Salinas

4.87 out of 5 average rating, 148 reviews

Adorable 1-bedroom guest house

Country-Esque living with a modern touch. This new guest house is bright, stylish, cute & warm. Offering a luxurious cal-king bed and a twin with top-of-the-line bedding, a full kitchen, cozy living room with smart TV & stunning travertine shower to freshen up after you’ve explored all Monterey Bay has to offer.