
Guesthouse vacation rentals in Oakland
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Top-rated guesthouse rentals in Oakland
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Family-friendly guest house rentals

Charming Cozy Cottage in Eco-Garden Oasis
This beautiful Oakland Oasis was better than I imagined it would be! This place exceeded my expectations! Coming through the gate the first night, to a path of twinkling lights leading us to our adorable cabin took my breath away! It was the perfect location for peace and quiet right in the middle of Oakland. My only regret is that I didn’t spend more time on the property. We flew in from out of state to visit friends and spent a lot of time out and about. I definitely want to come back to spend more time hanging out in the backyard with the goats and chickens. My 13-year-old loved the backyard, the trampoline and the animals. The location was very walkable and within several blocks of many restaurants and shops. We rented a car and street parking was easily accessible. Reinhardt Redwood Regional Park was only an 8 minute drive away and we spent most mornings walking through the mountains enjoying the beautiful trees and views of San Francisco. Highly recommend this listing!

Farm in the city & sweeping bayview
I had a magic few days at Lori and Mike's. I drive a VW passat and I found the drive up the mountain to be non-challenging and even very fun by the end. The hosts are cool and easy to get along with. A+ doggo. Hot tub was great. Pool was fun. I usually stay in SF when I'm in the Bay Area. This was much more lovely and relaxing, with SF close enough that going in for dinner or a show felt like it wasn't a big deal. 100% would recommend this place. I brought my cat and had my lady friend with me for a night. Everyone loved it.

Charming Cottage in Haight-Ashbury Garden
Our stay in Rosa's ADU could not have worked out better. Our kids live right up the block and it is a great location for so many things. We loved exploring Golden Gate Park and there were plenty of shops and restaurants within walking distance. Rosa was an excellent communicator and was attentive to our needs. She changed out our towels during the trip and restocked kleenex. Rosa and her husband are San Fran natives and supplied very interesting San Fran history and guide books in the unit as well. We will definitely be back!

Stand-alone cottage in garden setting, parking.
Very friendly and proactive host. Praceful and quiet location. Several pieces of lovely fruit were provided, as well as flavored sparkling water, milk, and granola/muesli, which was really convenient. Showerhead can be adjusted for angle and whether you want a straighter stream straight down, or a wider spray. I appreciated that there was a screen on the window so it was easy to get fresh air when I wanted while keeping bugs out. I suggest trying to time your arrival the first day during daylight hours, as that will make it easier to see the signs, especially when Google Maps is off by a few yards in terms of where it tells you to turn.

Little Cottage on the Hill
This was an EXCELLENT Airbnb. Great value, beautiful property, plenty of privacy, exceptionally good instructions form the hosts. I can not recommend highly enough. Great place to recharge.

Cottage near dwntwn Palo Alto, Stanford, Face-book
This was a perfect place to decompress during a busy work trip. The space is beautiful, and the attached gym is such a nice treat! Everything was exactly as described, clean and lovely. I would definitely stay again!

Backyard Beach House (BBH)
We enjoyed our stay at Barbara's charming Backyard Beach House for the third time, and felt at home there. We find it restful to stay in this quiet neighborhood. It's always nice to communicate with Barbara and Ken, as they are readily available if we have questions or requests. We consider this house a gem of a find. Thank you again Barbara and Ken for contributing to our lovely vacation.

Tropical Garden Cottage +HOT TUB &POOL by Downtown
I rented Polina’s place for my daughter and toddler grandson during their visit to the area because my husband and I did not have room for them to stay with us. It was an excellent choice - a lovely well maintained unit on the grounds of Polina and her family’s home in the hills above Walnut Creek. Very peaceful area, yet close to downtown and transportation options. Polina was so kind and helpful, the unit has everything one would need for a short stay in the area. Highly recommended and a good value for the area.
Guest house rentals with a patio

Sustainable Studio in Sunny San Rafael
This is an excellent choice for a visit to Marin. The interior makes such great use of space - plenty of outlets, beautiful Italian tiles, nice art, and extremely comfortable bed. There's also a cute outdoor patio that would be perfect for coffee, though we never took advantage. We walked to Trader Joe's and downtown is also an easy walk. It's quiet, peaceful, and the wifi worked great. Andrea also provides lots of extras, like oil, coffee, salt/pepper, etc. Everything you need to make a meal, which we did. Most couples travel with one car; our only hitch was needing two since we live in separate locations. Nevertheless, we figured out a way to use the space available and also find additional street parking with no constraints. Highly recommended!

Private garden retreat
I enjoyed my stay at Mary Lee and David’s place. It was perfectly located for my purposes, affording easy access to both the East Bay and Marin. The place is well appointed and clean, the entry through the backyard pretty, and the neighborhood charming. They were great hosts - available, but not hovering, their communication clear and timely.

Delightful Hideaway in San Carlos
Marilynn has been great and very responsive when we have stayed there. The place is well-stocked and maintained, and San Carlos is a friendly town with good restaurants and boutique shopping.

Boho beach bungalow- walk to Poplar Beach
Very cozy and private. I brought my family of four and we had a lovely time. The only tricky part is figure out how to lock the door, but if that’s the worst of it, then I’d say it was pretty amazing. It’s about a 15 minute walk to the beach along nature paths and side streets. Definitely worth it!

Sausalito Garden Stay
David is a great landlord. He was extremely fast to answer all questions. He was super helpful too!

Sunny, Peaceful Private Sanctuary
It’s a very private abode even though you share a gated entrance with the owner. Barry couldn’t have been friendlier and had a great spirt about him. We nerded out on landscaping, tiny homes, and rivers. He sold me on giving the American River some of my time this year. I’d absolutely stay here again. The only real issue was the effort to climb down a ladder half awake. I did it in the dark so I wouldn’t lose my cat eyes and wake up too fast. There’s plenty of outside lounging areas and the views are pretty. I had a decent view of the night sky to the east and above. The town may be busy but you’re perched hillside under some great live oaks. The neighborhood was full of quiet families and quirky houses that are truly Marin County in nature. Open space trails are just uphill and the town is just down. It’s very convenient to everything.

Silicon Valley Oasis
We felt right at home in this cozy Air bnb. The garden areas surrounding the property are beautiful. We had everything we needed and more in the kitchen where we made breakfast every morning. Lots of cookware and cabinet full of spices. Super clean. Bed was comfortable. Walking distance to downtown San Carlos was about 23 minutes. The host checked in regularly with us online and we appreciated the attention. Was sad to leave when our time was up. We hope to return as we have family in the area.

Mill Valley Garden View Guest House, Free Parking
This is an absolute hidden gem. It quickly became apparent why Carolyn is a super host. Not only is the property absolute perfection but Carolyn made it a point to go out of her way to welcome us, accommodate us, and go above and beyond customer service wise. This property radiates harmonious zen like energy from the community library, to its amenities and all its extra additives, to the garden. It’s graced with every bit of detail for guests to enjoy. I’ve loved traveling and have mostly been a hotel snob, until now. In short, Carolyn has carefully crafted a beautiful get away and decided to share it with the world. We will certainly be back when in town.
Guest house rentals with a washer and dryer

Lightworks Treehouse Retreat
My partner and I absolutely loved Sarah's place. It was super peaceful and relaxing being surrounded by the beautiful trees and hearing the sound of birds and the nearby creek. As soon as you walk in, you can tell Sarah puts alot of love and care to ensure anyone staying there feels comfortable. We really appreciated that and look forward to booking her place again when we need a relaxing retreat to rest and reset.

Easy commute Private guest suite
Helen's place is roomy with a well-equipped kitchen and a nice bathroom. The dishwasher and washer/dryer provided added convenience. The location is just off busy Woodside Road with a Safeway market about 5 minutes away on foot.

Private Cottage near Redwood City and San Carlos Downtowns
Great experience in every way. Nico was response and friendly. Place was just as described. Would definitely stay again

Studio at Surfers Outlook
This perfectly-appointed cabin in the sky was the ideal escape “between the years.” It rained every day of our stay but that did not stop us from walking down to the beach, grabbing a bite at Parkside Cafe, and exploring every hiking trail in walking distance. (Highly recommend the Dipsea trail to Steep Ravine with a side bar to the Stinson Tree.) Carey really thought of everything: not only was the bed comfy and the place spotlessly clean, the kitchen was well-equipped (cream for the coffee!) as was the bathroom (thick towels!) We especially appreciated the clear instructions for operating windows and other things. It was our best Airbnb experience to date and we can’t wait to come back.

Luxury 4BR House at Westlake near BART, Beach Golf
Was a good option for our group of 7 to stay. The hosts were prompt in helping out.

Redwood Casita
Jim’s place is located in a quiet neighborhood but easy to get to town. The bed is super comfortable. It is also nice to have the kitchen and dining area separate from the bedroom. Highly recommended!

Mission Casita, Walking Distance to DT San Rafael
We stayed at Matthew's place for 2 weeks and had a great stay. We highly recommend it to anyone visiting Marin! The location is incredibly convenient—right off the highway in central Marin—making it easy to explore the area. The house felt spacious for our family of 4 and everyone had enough room to work & relax. The kitchen was fully stocked and both the bedrooms & bathrooms were clean and comfortable. It's a well-maintained home so we had no complaints. Matthew and Tim were always available if we had questions and we highly recommend their house to anyone!

Convenient 3 bedroom guest house near SFO, highway
We chose this stay to host guests over the holidays and it had everything we could’ve needed. The kitchen was functional for cooking breakfast and the rooms were very private and had their own bathrooms. Xing Tian was very helpful when we needed an extra gate key, and when we had any questions. We’ll definitely be coming back!
Quick stats about guesthouse rentals in Oakland
Total rentals
380 properties
Total number of reviews
37K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
200 properties have a dedicated workspace
Wifi availability
380 properties include access to wifi
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- Golden Gate Park
- Stanford University
- Washington Square
- Joaquin Miller Park
- Children’S Fairyland
- Muir Woods National Monument
- Oracle Park
- Chandon
- Dominus Estate
- Golden Gate Bridge
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- Glen Canyon Park
- Big Basin Redwoods State Park
- Point Reyes National Seashore
- SAP Center
- Mission Dolores Park
- Oakland Zoo
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