Guesthouse vacation rentals in Monterey Bay

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Top-rated guesthouse rentals in Monterey Bay

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Santa Cruz

4.98 out of 5 average rating, 481 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

$141 per night

Guest favorite

Guesthouse in Pebble Beach

5.0 out of 5 average rating, 195 reviews

Short walk to the Lodge at Pebble Beach

The cottage is bright and cozy with its wood beams, wood floors and many windows. On sunny days enjoy the rays of sunshine coming through the windows, open the bedroom french doors and relax with a book and a glass of wine on the private, quiet terrace and let the world go by or sit by the french limestone fountain and listen to the soothing sound of water. In the evening or on rainy days, lounge in the living room area by a cozy fireplace and enjoy the peacefulness of your home away from home.

Sep 13 – 20

$675 per night

Guest favorite

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.

Jul 5 – 12

$134 per night

Guest favorite

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 19 – 26

$132 per night

Guest favorite

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 27 – Jun 3

$142 per night

Guest favorite

Guesthouse in Seaside

4.91 out of 5 average rating, 660 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.

Aug 20 – 27

$161 per night

Guest favorite

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 24 – Jul 1

$195 per night

Guest favorite

Guesthouse in Santa Cruz

4.97 out of 5 average rating, 628 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.

Sep 9 – 14

$153 per night

Guest favorite

Guesthouse in Watsonville

4.95 out of 5 average rating, 174 reviews

The Tanoak Casita + hottub and 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 30 – Oct 7

$189 per night

Guest favorite

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

$107 per night

Guest favorite

Guesthouse in Los Gatos

4.97 out of 5 average rating, 862 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 20 – 27

$204 per night

Guest favorite

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!

Sep 18 – 25

$187 per night