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)!

Family · Value · Cleanliness

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

Location · Family · Accuracy

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!

Location · Family · Air conditioning

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.

Family · Value · Access

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!

Value · Family · Long stay

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.

Family · Value · Getting around

Oakland Jungalow Cabin Studio

Take a break and unwind at my outdoor oasis. Experience Oakland and the Bay Area from a cozy cabin with tons of outdoor space, deck seating, fruit trees for picking, walking distance to some of the best tacos and pastries in the Bay Area. Easy entry to every part of the SF Bay Area with public transport (BART) 10 min walking. I live on property with my 6 yo and a few cats, but everything is self service with private entrance. I'll stay out of your way. Enjoy!

Value · Family · Sleep quality

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

Family · Value · Nearby

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.

Value · Family · Comfort

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.

Value · Location · Parks

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

Value · Location · Nearby

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.

Family · Location · Kitchen