Guesthouse vacation rentals in Monterey Bay

Find and book unique guesthouse rentals on Airbnb

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 Santa Cruz

4.98 out of 5 average rating, 480 reviews

Garden Oasis Guesthouse Relax, Surf & Adventure

Welcome to our Artistic Garden retreat! Centrally located in the heart of Santa Cruz, 1 mile from Sunny Cove Beach and Pleasure Point. Close to the boardwalk, yacht harbor, Downtown Santa Cruz & Capitola. Detached guesthouse & spacious lush yard, fully furnished, outdoor area and more. Our 1/2 acre farmhouse lot is a garden oasis with lush palms, proteas, bamboo & succulents weaving throughout. Our garden and private lot have it all! 1 night stay ok when available just ask. No animals allowed.

Aug. 22 – 29

$261 CAD per night

Guest favourite

Guesthouse in Boulder Creek

4.99 out of 5 average rating, 149 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.

May 28 – Jun. 4

$245 CAD per night

Guest favourite

Guesthouse in Monte Sereno

4.97 out of 5 average rating, 387 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.

Sep. 22 – 29

$228 CAD per night

Guest favourite

Guesthouse in Salinas

4.99 out of 5 average rating, 488 reviews

La Casita de Fuerte.

Great S. Salinas neighborhood within walking distance to Old Town. In Old Town you will find great restaurants, places to get a drink, nightlife, and movie theater. Centrally located, 100 miles to San Francisco, 15 miles to Monterey Peninsula (Fisherman's Wharf, Aquarium, Pacific Grove, & Carmel). The unit is brand new. Cozy, sunny, and spacious, with lots of privacy. There is a Microwave, Keurig, and mini-fridge (no freezer) available for use. There is NO stove, oven, or air-conditioning.

May 14 – 21

$217 CAD per night

Guest favourite

Guesthouse in Seaside

4.89 out of 5 average rating, 929 reviews

Cozy Seaside Cottage

Cozy Seaside cottage conveniently located in a friendly neighborhood in Seaside. Our slice by the sea is close to the beach, Monterey fairgrounds, Laguna Seca Raceway and more! Enjoy a quiet stay in Monterey bay with a private driveway and patio area as well as a full laundry room and fully stocked kitchen. New carpet and a recently renovated bathroom are an added plus! Walking distance to grocery stores, Walgreens, and local restaurants. Perfect retreat for a couple or just you!

Jun. 14 – 21

$330 CAD per night

Guest favourite

Guesthouse in Marina

4.85 out of 5 average rating, 457 reviews

Affordable Tiny House Miles From the Beach!

Completely re-modeled tiny house just miles from the beach! My goal is to offer an affordable, clean space to travelers. This tiny house is not perfect at 130 quirky sq. ft. but is detached from our main house. It’s perfect for a weekend getaway! Full size bed & private bathroom. Stocked with refrigerator, microwave, Keurig, towels, cups, wifi, silverware, hair dryer, etc. Separate entrance through a locked gate in our secure backyard. Sorry, no kitchen in the space or laundry.

Jul. 11 – 18

$249 CAD per night

Guest favourite

Guesthouse in Santa Cruz

4.97 out of 5 average rating, 627 reviews

Upper WS Guesthouse-2mi. from UC, Downtown & Beach

This detached guesthouse, recently updated in May 2023, is 500 sq. ft and 20ft. away from the main house. It’s located up the driveway & tucked away on the right side of the property. Perfect for 2 people but can sleep 3-4 (convertible couch OR queen air mattress). Close to popular destinations such as: UC Santa Cruz campus (approx. 2 miles), Boardwalk, desired beaches (approx. 2 miles), downtown Santa Cruz, hiking trails etc. Fully furnished guesthouse w/washer & dryer.

Apr. 18 – 25

$237 CAD per night

Guest favourite

Guesthouse in Watsonville

4.95 out of 5 average rating, 172 reviews

*Tanoak Casita* Tree House + Hot Tub +Aquarium Tix

Walk up the steps under the indigenous and mystical Tanoak and into your idyllic getaway, curving around Coast Live Oak tree and settled under the shade of Redwoods. You'll feel as if you're up in the canopy while completely earthed into the landscape, surrounded by natural plaster walls and clean-line minimalist details. Enjoy the hot tub overlooking the tree canopy. 2-night reservations include 2x free guest passes to the Monterey Bay Aquarium! See more details below.

Sep. 9 – 16

$348 CAD per night

Guest favourite

Guesthouse in Felton

4.85 out of 5 average rating, 178 reviews

Private Retreat Studio

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 has a private entrance, kitchenette, bathroom and gas fireplace. Deck surrounded by redwoods, with outdoor grill, is partitioned for privacy. Studio is good for couples and solo travelers.

Jun. 7 – 14

$212 CAD per night

Guest favourite

Guesthouse in Los Gatos

4.97 out of 5 average rating, 860 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!

Jul. 16 – 23

$319 CAD per night

Guest favourite

Guesthouse in Moss Landing

4.96 out of 5 average rating, 183 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!

Jul. 26 – Aug. 2

$297 CAD per night

Guest favourite

Guesthouse in La Honda

4.95 out of 5 average rating, 382 reviews

Bicycle Shack @ La Honda Pottery

My place is close to miles of hiking and biking trails in county parks and openspace, great views, the beach and not far from the Peninsula, S.F. and Santa Cruz. You’ll love my place because of the location, the people, the ambiance, the outdoors space and that it is a self contained small cabin with a tiny deck.. My place is good for couples, solo adventurers, and furry friends (pets). Perfect for hikers and bikers.

Jan. 24 – 31

$165 CAD per night