Guesthouse holiday rentals in Oakland

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Top-rated Guesthouses in Oakland

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

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Guest favourite
Guesthouse in Rockridge
4.88 out of 5 average rating, 327 reviews

The Rockridge Cottage

The Rockridge Cottage is a lovely stand alone backhouse in the most central location in the East Bay. Enjoy the peaceful backyard and privacy of your own home and be steps away from the world class restaurants and cafes of College Avenue. Located just three blocks away from the Rockridge BART Station, the Rockridge Cottage is only 25 minutes from Downtown San Francisco and just down the road from the UC Berkeley campus. Walk Score of 92. There is no need to have a car in this neighborhood.

Top Guest favourite
Guesthouse in Eastmont Hills
4.98 out of 5 average rating, 187 reviews

Serene foothills Garden Suite, private parking +EV

Have the entire Bay Area at your fingertips... & right outside your window! This private studio tucked into the Oakland Foothills is the perfect base for adventures. A 9min drive & you can be on the train into San Francisco. Coliseum & redwoods are minutes away, as are many other attractions*. You’ll be welcomed home to a comfy Cal King bed & a serene garden view. Enjoy coffee/tea as you settle in at the table, & our high speed wifi has you covered. Have an EV? Charge Level 2 overnight (J1772)!

Guest favourite
The exterior of a two-story home is surrounded by lush greenery, with a driveway leading to a detached garage. Soft lighting from lanterns illuminates the path. Flower boxes adorn the windows, adding a touch of color to the calm, inviting facade.
Guesthouse in Oakmore
4.92 out of 5 average rating, 528 reviews

Redwood Sanctuary Oakland Hills

Redwood Sanctuary is located in the idyllic Oakland Hills with beautiful vistas, hikes, and parks within a short drive. The home is situated on half an acre of land in the middle of redwood, eucalyptus, and oak trees secluded away from other homes. Montclair village is an 8 minute drive, providing lots of great food and shops. Minutes from Highway 13 and 580. It is a 1 bedroom studio with a queen bed and a pull out sofa bed. It can comfortably accommodate up to 3. We'd love to host your stay!

Guest favourite
An exterior view of the ADU features a dedicated entrance with wooden steps leading to a deck. A pathway of stones is surrounded by gravel and greenery. The shingled walls of both the ADU and main house are visible in a tranquil setting.
Guesthouse in Grand Lake
4.89 out of 5 average rating, 159 reviews

Quiet space, great location!

Spacious single room ADU with vaulted ceilings, queen bed, and natural light. Access to a large yard with beautiful views. A new private bathroom is just outside, steps away in the main house. Located in a quiet, safe neighborhood near Grand Lake Theater, Lake Merritt, Morcom Rose Garden, restaurants, and shopping. Minutes to Berkeley, Piedmont, downtown Oakland, and public transport to SF. Dedicated entrance to room. No kitchen - mini fridge, coffee pot, kettle included for your convenience.

Top Guest favourite
A lush garden surrounds the cozy cottage, featuring diverse plants and greenery. Raised garden beds filled with herbs and vegetables complement the gravel pathway leading to the cottage. The exterior features light-colored siding and a muted gray door, merging with the natural landscape.
Guesthouse in Oakland
4.87 out of 5 average rating, 358 reviews

Rockridge Garden Cottage

The cottage is newly remodeled as of March 2022 and now has its own kitchen and bathroom. It is a separate unit in my backyard with vaulted ceilings which gives a spacious feel and french doors that open onto the lush garden. Queen size high end natural organic fiber bed (Earthsake.com), with down comforter + 4 pillows. Dining table and stools. LCD TV, clothes valet, work desk and great internet. Its very quiet and my guests seem to love having a private retreat type space to themselves.

Top Guest favourite
Guesthouse in Alameda
4.94 out of 5 average rating, 252 reviews

Cute, backyard Cottage w/ close access to all!

Great space for a lovely trip to the Bay Area! Located in a very safe & quiet neighborhood of Alameda. The cottage has a private bathroom with shower (no tub), a kitchenette with microwave, and the most comfortable queen bed. Close to Oakland Coliseum, BART, SF, Oakland Airport, and ferry to SF. Great access to Bay Farm Trail and just a short walk to restaurants and shopping. ** Please note that the bed is against the wall, so if you are a group of two, one person will be against the wall.

Guest favourite
The exterior showcases a detached studio, accentuated by string lights that frame the entrance. Sliding glass doors lead to the interior, revealing glimpses of a cozy living space and a modern kitchenette. A wooden deck with outdoor seating complements the inviting atmosphere.
Guesthouse in Glenview
4.91 out of 5 average rating, 327 reviews

Private, Detached, Urban Creekside Studio.

This unique, well equipped, 1 Bed cute little studio (that we love) is detached and fenced off from our main house. It has a separate entrance through a side gate and it's own private rear deck, with a seating and dining area... that overlooks Sausal Creek and Dimond Park. The tall willow that grows along the creek gives the deck the perfect amount of privacy and with the tranquil sound of the creek flowing (not during dry season) you would almost forget you are in an urban city.

Top Guest favourite
An outdoor dining area is furnished with a large wooden farm table surrounded by metal chairs, set on a pebble-covered surface. A cozy golden retriever relaxes nearby, amidst lush greenery and decorative landscaping elements, while string lights hang overhead, enhancing the garden's inviting charm.
Guesthouse in Oakland
4.97 out of 5 average rating, 572 reviews

Luxury Rockridge Casita in Our Sunny Garden

** FEATURED in Sunset Magazine ** Our bright modern guest house with private access awaits you. Retreat from the city to our comfortable, clean casita. This lovely, light-filled space sits behind our family home, in our garden with fresh berries and lemons. Enjoy morning coffee at the wood farm table. We offer local coffee + tea, a small fridge, robes, wifi, and outdoor dining. Our quiet street is close to BART, 3 blocks from College Ave, full of great restaurants and shops.

Top Guest favourite
A cozy interior of a cabin is showcased, featuring a lofted sleeping area accessed by a wooden ladder. Below, a spacious bed is positioned near windows that invite natural light. A small dining table with chairs and bookshelves add functionality to the warm wooden space.
Guesthouse in Redwood Heights
4.96 out of 5 average rating, 249 reviews

Charming Cozy Cottage in Eco-Garden Oasis

Our charming cottage is a relaxing retreat in the city! Our sweet cabin is small and cozy set in an expansive garden oasis. We offer a unique experience for those interested in a beautiful and tranquil escape in the heart of the city. The cottage is at the back of our large garden with views of our beautiful urban farm with a pond, chickens and goats! Families with up to 2 children are best suited for the loft because of the low ceiling. No more than 2 adults please.

Guest favourite
Guesthouse in Peralta Hacienda
4.9 out of 5 average rating, 100 reviews

Comfy 2 bedroom cottage centrally located

Welcome to the cozy Oakland cottage, located behind the main house separated by a fence with exclusive use of the space. Ideally located for exploring Oakland and San Francisco, just one mile from BART, 20 minutes to SF, and close to major freeways. In less than 15 minutes you can reach Lake Merritt, Joaquin Miller Park’s redwood trails, and some of Oakland’s food, and local spots—while still having a peaceful place to recharge.

Top Guest favourite
A spacious yard is encircled by lush greenery and mature trees, creating a private outdoor setting. A stone fireplace is visible near a charming garden shed. Patio furniture, including chairs and a table, is arranged invitingly on the grass, ideal for outdoor meals.
Guesthouse in Crocker Highlands
4.96 out of 5 average rating, 598 reviews

Lakeshore Cottage

Our quiet studio cottage is located in the Lakeshore/Grand Ave area of Oakland. The neighborhood is safe and beautiful and the cottage is neat and easily accessible. There is a large bright main room and a spacious bathroom that was recently updated. The cottage includes a mini kitchen. The location is close to downtown Oakland, Berkeley and San Francisco.

Top Guest favourite
The charming cottage exterior features natural wood siding, framed by greenery and vibrant flowers. A welcoming entrance is visible, along with a small deck furnished with two chairs and a table, offering a cozy spot for outdoor relaxation.
Guesthouse in Kensington
4.95 out of 5 average rating, 740 reviews

Secluded luxury cottage & hot tub

Surrounded by trees on 1/2 acre, our cottage in Kensington/ Berkeley Hills is a perfect country house in the city. Our relaxing light-filled retreat is decorated with our original textile designs, Kiran's fine art photography and has a hot tub available for the guests under the stars.

Popular amenities for Oakland guesthouses

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Quick stats about guesthouse rentals in Oakland

  • Total holiday rentals

    Explore 380 holiday rentals in Oakland

  • Verified guest reviews

    Over 39,120 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wi-Fi availability

    380 of Oakland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakland rentals

  • 4.9 Average rating

    Oakland stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Oakland's top spots, include Oakland Zoo, Jack London Square, and Joaquin Miller Park

Destinations to explore