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)!

Pool, Jacuzzi, Sauna, Huge Views, gated, ADU

Stunning, ADU cottage w/ higher end finishes. Endless VIEWS of mountains set on a beautiful, peaceful, upscale gated, property surrounded by redwood, pine & oak trees. 1 mile to large regional parks for hiking, mountain biking and horse stables. Nature at its best! Pool heated May 31st to October 30th. 16 miles to San Francisco, 5-10 minutes to many restaurants. New Jacuzzi and outdoor sauna. Large patio, pool / deck (6500 sq foot outdoor oasis shared with main house with a small family of 4)

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!

Private suite on 1918 heritage property

Originally settled in 1918 this heritage property, situated in Concord’s most coveted neighborhood boasts warm, old-world charm and timeless finishes while incorporating the modern amenities. Fully furnished & welcoming studio features a well-appointed kitchen, laundry and spa inspired bathroom. The adjoining patio is the perfect venue for enjoying morning coffee or evening cocktails. The incredible 1 acre lot, intersected by the spring-fed Galindo Creek has plentiful on-site parking!

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.

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.

Cozy & Secure Oakland Retreat for 4, Pets Welcome!

Your Private Temescal Retreat: Pet-Friendly & Walkable Escape to a cozy, pet-friendly retreat perfect for couples, small families, or travelers seeking a relaxing getaway. This charming home offers a comfortable, inviting space where you can unwind, enjoy quality time together, and bring your furry friends along. Whether you’re enjoying a quiet morning coffee, exploring nearby attractions, or simply relaxing indoors, this home makes every stay comfortable and memorable.

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 Accessed by a private entrance, the cabins are luminous and efficient, designed to meet all your needs.

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.

Charming Victorian Retreat

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 West Oakland BART & nearby freeways access offer quick and easy commute options to San Francisco and downtown Oakland, greater East Bay and South Bay

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.