Guesthouse holiday rentals in Oakland

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)!

Heauxtel (hōˈtel) Serenity

This Airbnb is a cultural experience, and it might not be for you. That’s ok. A meaningful specific can’t possibly please everyone. Racism, sexism, homophobia, etc have no place here. We are a predominantly Spanish-speaking community. You can purchase fresh Tamales, Pupusas, etc from our street vendors. We are next to an elementary school on a semi-busy street. You may hear roosters in the morning. You will see litter on the ground. You may hear loud trucks driving past. Password: #oaklandvibes

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!

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.

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.

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!

The Purple Door, Private Sanctuary, Epic View

Private guesthouse located in the Oakland Hills with stunning views of the bay. We recognize the importance of privacy, this guesthouse will allow you to have everything you need all while never having to be bothered. The sunset views can be taken in from your bed or the deck. There is a bus stop about 150 yards away if you need, the airport is about a 7 minute ride away, rail (BART) is about 5 minutes and the house is near a freeway for quick access to everywhere in the Bay Area.

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.

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

Cozy Private Entrance Studio

Keep it simple at this peaceful and centrally-located space. Whether you’re visiting for a few days or a month this unit/location has everything you’ll need. Close to wildlife/great trails/lookouts, 10 minutes from downtown Oakland, and just 30 minutes from San Francisco. Perks include open parking, easy access to the freeway, and a quiet neighborhood.

Charming Rockridge Cottage| Walkers’ Paradise

Location, location, location! Fall in love with Rockridge from this charming, backyard standalone cottage! Just a stroll to BART & College Ave’s foodie gems—Acre, Belotti, Market Hall & Trader Joe’s. 15mi to SF, 3mi to UC Berkeley & hospitals. Perfect for 1–2 adults, price based on occupancy. Fur babies welcome (with fee)!

Modern Sunny Rockridge Cottage

Our beautiful, modern cottage is private and sun filled. The cottage fits one or two people, with a full-sized loft bed and a sofa that could very comfortably sleep a single. We are just two blocks from Bart and 20 minutes into SF. We are a block from lovely restaurants, cafes, and shops.