Guesthouse vacation rentals in Oakland

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Quick stats about guesthouse rentals in Oakland

  • Total vacation rentals

    Explore 370 vacation rentals in Oakland

  • Verified guest reviews

    Over 42,140 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wi-Fi availability

    370 of Oakland vacation 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 Alameda Beach

Top-rated guesthouse rentals in Oakland

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

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Top guest favorite
A dining area is shown, featuring a light wooden table set for two with plates and glasses. Two gray chairs are neatly arranged around the table. A potted plant adds a touch of greenery, positioned near a bright window with a light-filtering shade.
Guesthouse in Oakland
4.98 out of 5 average rating, 218 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 favorite
A spacious driveway leads to a well-maintained home nestled among trees. The house features a light-colored exterior and is complemented by warm lighting around the entrance. Landscaping includes bushes and flowers, enhancing the natural setting.
Guesthouse in Oakland
4.91 out of 5 average rating, 568 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!

Top guest favorite
Guesthouse in Oakland
4.97 out of 5 average rating, 611 reviews

Luxury Rockridge Casita in Our Sunny Garden

Featured in Sunset Magazine ✨ Tucked into our sunny Rockridge garden, this light-filled modern casita is a peaceful retreat — 3 blocks from College Avenue’s cafés, restaurants, and shops. Wake up to birds in the garden, sip coffee at the farmhouse table, and walk to BART for easy access to San Francisco, Berkeley, and downtown Oakland. A quiet space designed for those who appreciate beauty and thoughtful details. Ideal for couples exploring Rockridge, Berkeley, Oakland, and San Francisco.

Superhost
The image depicts a serene garden pathway leading to two adjacent cabins, framed by vibrant greenery and flowering plants. A wooden trellis is visible, providing shelter, while soft lighting from the cabins enhances the calm atmosphere. A mixture of stone and mulch surfaces directs attention toward the entrance.
Guesthouse in Oakland
4.9 out of 5 average rating, 429 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 Again, you get both! Accessed by a private entrance, the cabins are luminous and efficient, designed to meet all your needs.

Top guest favorite
A cozy living area is presented with a rustic wooden accent wall and a flat-screen television mounted for entertainment. A spacious coffee table sits centrally with candles, accompanied by a modern yellow and blue sofa, while an armchair with a bright green cushion adds a touch of color.
Guesthouse in Oakland
4.97 out of 5 average rating, 230 reviews

The Redwood Retreat

Near Lake Temescal, Redwd Regional Prk, Bart, Hwy 13, Rockridge,Montclair, Dwntwn. We completely remodeled our guest house with a focus on short term tenants. Lots of storage within one of the most quite settings you will find. We made a thoughtful attempt to load the unit with everything u might need while away. The kitchen is functional to the point that you could actually cook a Thanksgiving dinner, multiple frying pans to crock pots a blender or chefs knives. Bathroom sundries abound!

Top guest favorite
A modern living space features a light-colored sofa with decorative pillows, positioned near floor-to-ceiling windows with golden curtains. A retro-style green refrigerator and a light-colored coffee table are visible. A soft area rug rests on warm wooden flooring, contributing to a cozy ambiance.
Guesthouse in Oakland
4.98 out of 5 average rating, 101 reviews

Chic ADU in Redwood Heights

Stay in this newly remodeled 1-bedroom ADU in Oakland’s peaceful Redwood Heights neighborhood. With a full kitchen, walk-in closet, modern bathroom, in-unit washer/dryer, Wi-Fi, heating, and AC, it has all the essentials for a comfortable stay. Enjoy hassle-free self check-in/out and ample street parking. Located in a beautiful, quiet neighborhood, close to freeways, Laurel Heights shopping, and stunning hiking trails. A cozy, convenient stay awaits you in Redwood Heights!

Top guest favorite
A spacious studio is framed by a high ceiling featuring a modern light fixture. A comfortable queen bed is dressed in neutral tones, accompanied by plush pillows and a throw blanket. In the background, a dining area displays a table with chairs, and art is showcased on the walls.
Guesthouse in Oakland
4.97 out of 5 average rating, 108 reviews

Rockridge Garden Guest House with Hot Tub

Come stay in our bright and centrally-located backyard garden studio. Our modern, peaceful, bright space with private access awaits you. Located behind our home, the studio guest house has the best of both worlds - quiet residential neighborhood, but close to everything in Rockridge! The guest house is 4 blocks from BART, giving you easy access to San Francisco and all the Bay Area has to offer! 2 blocks from College Ave, with shops and restaurants and coffee.

Superhost
A bright living room features large windows allowing natural light, framed with sheer white curtains. The space includes a comfortable white sofa, a round coffee table, and decorative accents like a geometric art piece and sunflowers placed on the table.
Guesthouse in West Oakland
4.94 out of 5 average rating, 143 reviews

Charming Victorian Retreat | Minutes to SF

Welcome to your Victorian retreat in the heart of West Oakland! 4 BD - 2 BT - 1 off-street parking, uniquely blend of historic charm and modern comfort, has everything you need for a home base for your vacation or work trip. Located in the West Oakland neighborhood, just few short blocks from BART station & nearby freeways access offer quick and easy commute options to San Francisco and downtown Oakland, greater East Bay and South Bay

Guest favorite
The exterior of the casita is showcased with a charming entrance door framed by well-maintained landscaping. Soft lighting highlights the inviting windows and pathway made of natural stone, leading guests to the entrance amid lush greenery.
Guesthouse in Berkeley
4.92 out of 5 average rating, 594 reviews

Claremont Casita with a View

Welcome to the Claremont Casita, a Spanish-style guest house that sits at the top of our property. Enjoy views of the Claremont hills, outdoor space to relax, a fully appointed kitchen (everything but an oven), Tempur-Pedic queen bed, and comfortable common areas, all in a beautiful neighborhood that is walking distance from Claremont shops, Rockridge, and close to BART and freeways. Ample street parking is available.

Top guest favorite
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 Oakland
4.96 out of 5 average rating, 636 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.

Guest favorite
The room features traditional tatami mat flooring and a low wooden table surrounded by floor cushions. A wood-burning stove stands against one wall, contributing to the rustic atmosphere. Light floods in from the skylight above, illuminating the inviting space with natural warmth.
Guesthouse in North Berkeley
4.84 out of 5 average rating, 1472 reviews

Traditional Japanese Tea House

Traditional Japanese architecture tucked away in a great Berkeley neighborhood. Peaceful and quiet but just a few blocks to UC Berkeley, all the restaurants of the "Gourmet Ghetto", and the North Berkeley Bart station. Brand new and very easy to use heater/air conditioner installed in March 2023 Berkeley Short Term Rental Registration # ZCSTR2017-0007

Top guest favorite
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, 787 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 guesthouse rentals

When is the best time to visit Oakland?

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Avg. priceG$22,994 GYDG$24,039 GYDG$24,039 GYDG$24,039 GYDG$25,084 GYDG$25,084 GYDG$23,830 GYDG$24,039 GYDG$23,412 GYDG$23,830 GYDG$22,994 GYDG$23,203 GYD
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Destinations to explore