Guesthouse vacation rentals in Oakland

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Top-rated guesthouse rentals in Oakland

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

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Guest favorite

Guesthouse in San Rafael

4.96 out of 5 average rating, 112 reviews

Your private hillside retreat, sunset views, pool

Welcome to your retreat! Drive through the gate to a peaceful secluded setting. Watch the sunset from your private deck in the hills above San Rafael. Like a treehouse but with no stairs! Modern, designed by sixty nine EDGE Design, and completely renovated in 2023. Separate building from main house. Pool with a big view is heated May - September. Centrally located between San Francisco, Mill Valley, Sausalito, Napa, and Sonoma. Guests like the bed. TV: Netflix, Hulu, Disney+, live sports, more+!

Guest favorite

Guesthouse in Lower Haight

4.98 out of 5 average rating, 322 reviews

Charming Cottage in Haight-Ashbury Garden

Our deluxe cottage is close to Nopa, Nopalito, Ragazza, Bar Crudo, Barvale, Souvla, Buena Vista Park, Alamo square and the painted ladies, Haight Ashbury, Golden Gate Park, Fallettis market and BiRite market. Tastefully appointed and with luxury linens you’ll love our place because you can walk or take bus easily from here, very quiet with peaceful yard and the bed is supercomfy. You will get a great night's sleep here. Our place is good for couples, solo adventurers, and business travelers.

Guest favorite

Guesthouse in Half Moon Bay

4.9 out of 5 average rating, 250 reviews

Stylish Spacious Seaside Retreat, Walking to Beach

A perfect getaway on the coast with fresh air, sandy beaches, biking/hiking trails, and quaint restaurants, our place is 10minutes walk to the famous Maverick Beach, Sam Chowder House, and the Harbor. This stylish guest house is the 1st floor of our seldom used beach house in El Granada, 4 miles north of Half Moon Bay. It has a private entry, a fully equipped kitchen, w/ a laundry/mud room & on-site parking. Large decks have splendid ocean view! Come and enjoy this quiet and comfortable home.

Guest favorite

Guesthouse in Danville

4.88 out of 5 average rating, 268 reviews

Welcoming Private Guesthouse

Private entrance with direct access to Iron Horse Trail. Freestanding unit with bedroom, living room, kitchenette (not full kitchen) and bathroom. Walkable to Downtown Danville. Visiting family in Alamo, Danville, Lafayette, San Ramon or WC- inquire about the Family or CPC Events discounts. Set on 1/2 acre estate, walking distance to village. Coffee shops, bars, restaurants and family friendly pubs, Hot Summer Nights car show and Farmers Market. SF, Wine Country and Silicon Valley ~ 1 hour

Guest favorite

Guesthouse in Walnut Creek

4.97 out of 5 average rating, 158 reviews

Gorgeous Guest House with a Farmhouse Flair

Gorgeous new guest house tucked away from it all and yet close to Downtown Walnut Creek! Walnut Creek is truly a gem of a city right out side San Francisco with cutting-edge restaurants and retail shopping. Staying in our guest house will give you a taste of the country in a organic setting of the yard. This open floor plan is bright and airy, spacious kitchen with large peninsula view for eating and socializing. Beautiful front porch perfect for warm summer nights, with views of the hills.

Guest favorite

Guesthouse in El Sobrante

4.98 out of 5 average rating, 100 reviews

Hidden Gem in the Valley

The guest house is nestled in the May Valley, where views of the surrounding hills await from the primary bedroom and private backyard, surrounded by orange, plum, and persimmon trees. It's central location makes it ideal to explore the Bay Area's top attractions, including San Francisco, Napa Valley, Sausalito among others. With easy access to grocery stores like Target, Safeway, Lucky, Riley's, Trader Joe's, Sprouts and many more, you'll have everything you need for a comfortable stay.

Guest favorite

Guesthouse in Tamalpais Valley

4.89 out of 5 average rating, 498 reviews

Stunning & Tranquil Cottage with a Magical View

Stunning, tranquil, and private cottage in Tamalpais Valley neighborhood of Mill Valley. 100% renovated. Surrounded by the beautiful hills of Marin Headlands. Close to all Bay Area attractions. Muir Woods, Stinson Beach, Mt. Tamalpais, Angel Island, Sausalito, San Francisco. Many hiking trails very close by. Walking distance to Good Earth Market, Equator Coffee, Prooflab Surfshop, Shoreline Coffee Shop, + much more. True gem that leaves you relaxed, invigorated, and wanting to return.

Guest favorite

Guesthouse in San Rafael

4.88 out of 5 average rating, 179 reviews

Beautiful Guesthouse with direct view of the Bay

Beautiful furnished guesthouse located in east San Rafael, with a spectacular view of the water and Richmond Bridge. Located only a few minutes away from San Rafael downtown, where there is an abundance of coffee shops, restaurants, and bars. It is also walking distance from Trader Joe’s and Whole Foods. Guesthouse comes equipped with a queen sized bed (Saatva luxury mattress), pull out sofa, and a kitchenette. Beautiful oasis. 40 mins from wine country and 25 mins from SF.

Guest favorite

Guesthouse in San Rafael

4.97 out of 5 average rating, 357 reviews

Coleman Cottage - Hillside Paradise

Open, airy, private guesthouse in the San Rafael Hills of Marin County. Recently remodeled and completely refurnished with new appliances this beautiful setting affords all of the amenities and comforts for a home away from home. Located 20 minutes from San Francisco and 30 minutes from wine country with nearby hiking and biking trails, you will experience the best of the Bay Area. ** We are in compliance with all Covid-19 protocols and policies as set forth by Marin County. **

Guest favorite

Guesthouse in Redwood City

4.96 out of 5 average rating, 411 reviews

🌼Modern guesthouse w private patio and ♨️ hot tub

New and modern guesthouse, built in 2018, 20 min walk to downtown Redwood City. The kitchen comes fully equipped with high-end appliances, quartz countertops, Keurig coffee maker, and an eat-in island. In the living room, enjoy the 55" 4K TV with Bose sound on a sectional sofa that doubles as a pull-out bed. Rest well on a premium cal king size bed and enjoy a relaxing dip in the hot tub on your tranquil backyard patio. Unit has washer/dryer, heat/AC, and ensuite bath.

Guest favorite

Guesthouse in Oakland

4.91 out of 5 average rating, 302 reviews

Guesthouse Garden Retreat

Our 'sister guesthouses' consist of two small side-by-side cabins (you get both) located behind our home, nestled in a verdant hillside garden that our friends and family lovingly call ‘Little Tuscany’. Cabin 1 - living room with a well-stocked kitchenette, pull-out couch, table and chairs Cabin 2 - bedroom with a queen-size bed, full bathroom and a private deck Accessed by a private entrance, the cabins are luminous and efficient, designed to meet all your needs.

Guest favorite

Guesthouse in Alameda

4.85 out of 5 average rating, 110 reviews

Entire Guest House with Private Patio

Tranquil 1 bedroom 1 bathroom guest house. The space is calm and serene nestled in a lush urban garden surrounded by trees. Prime location where guests are walking distance from neighborhood cafes, and Downtown Alameda which has an assortment of excellent restaurants, bars, and shopping. Amenities include: Queen Bed with pillow top 42 inch Smart TV with Disney Plus & Hulu Private Wifi And More... Early check-in starting at 12pm an additional $35.