Holiday houses in Oakland

Step back in time on this beautiful classic yacht

Good Luck is a hundred-year-old classic yacht, lovingly restored and ready to transport you to another time while luxuriously spoiling you on your bay area adventure. This dockside charter gives you complete privacy and an amazing nautical experience. Alameda is a beautiful island community in the heart of the Bay, filled with beautiful homes, adorable shops, and many great restaurants. The San Francisco ferry is close by to whisk you to the big city, so why would you want to stay anywhere else?

Sunset Spa Suite w/private patio, views & parking

This private suite is a slice of heaven in a woodland setting! Accessed via a flight of garden stairs, it has a private entry, dedicated street parking, a private patio, luxurious large bath with a walk-in shower for 2, large jacuzzi tub for 2, heated floors, A.C., mini fridge, toaster oven, & microwave! The bedroom features a queen-sized bed, table for two, large screen smart TV, and strong fiber optic WIFI signal. Located in a beautiful neighborhood with wonderful hikes just outside the door.

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!

Modern 2 bedroom with stunning bay views

Kick back and relax in this calm, stylish space. The Oakland Hills are filled with amazing hiking, this location is great for day trips to Napa (35 miles), San Francisco (11 miles) or Carmel (120 m). Centrally located for work or play. This open concept 2 bedroom is a peaceful break away. Given the open concept design - there is not a lot of privacy between bedrooms, just a big bookcase room divider b/w the rooms. There are a few sitting area's outside and a green roof too! And EV charging.

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.

East Bay Studio Oasis - Rest, Relax, Or See It All

Cozy, clean studio apt located in the heart of North Oakland’s trendiest neighborhood. Renovated w/ kitchenette, stove/oven, fridge; large shower, cable TV, private entrance & porch. Queen size bed & small futon appropriate for a child or small adult. Walk to Temescal neighborhood for shops & foodies! Access to 3 BART stations, UC Berkeley, & the freeway. Awesome neighbors & sunny backyard for guests. Downstairs attached to main house. Located in Oakland ACROSS THE BAY from 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!

Sunlit Oakland Retreat w/ Designer Touches & Deck

Sunlight + greenery + indoor-outdoor flow to the deck. Perfect for remote workers, couples, or friends looking for a calm, design-forward retreat. Not suitable for toddlers. Located in the heart of sought-after Piedmont Avenue district. Why you’ll love it: • Premier Walk Score of 96 – enjoy cafés, boutiques just steps away • Michelin 2-star dining around the corner, along with many local favorites • Gourmet kitchen – fully equipped and stocked • Private deck nestled among mature trees

Sunny Temescal Jewelbox Studio

Sunny furnished 2nd floor apartment in the heart of the trendy Temescal neighborhood. Quiet back of the house location w/ private entrance. Offers modern comforts like new kitchen & bathroom with heated flooring. Fully equipped kitchen w/ induction stovetop, microwave/convection oven. Wi-fi & wired internet on gigabit fiber plus 43" Roku 4k TV. Sleeps 2-4 with sofa bed. Option for off street parking. Self check-in with personal gate code & lockbox. Close proximity to several hospitals:

Safe, clean, quiet studio (Close to SF, Hospitals)

Nestled in a serene neighborhood, our studio offers the perfect blend of comfort, convenience, and tranquility. As you step in through your private entrance, you'll find yourself in a cozy haven designed for your relaxation and enjoyment. Our studio is in a central location with easy access to downtown Oakland, Lake Merritt, and SF. Please note this is an in-law unit with shared walls. Guests must walk down a sloped concrete driveway with one step to access the space.

Hike-in Bay Views Cabin w HotTub

Hike up to a well designed, small-but-mighty modern cabin with fast WiFi, your own hot tub and a panoramic view spanning across the bay from the Golden Gate to the San Mateo bridge. 108 stairs lead up to the Aerie, so if you don’t want to get your steps in, this is probably not the space for you! 15 min from OAK and city life, but a world away. Sunsets are glorious here. The Aerie is a special spot just for 1 or 2, so leave the posse behind. Registered guests only.

Private In-Law Suite Historic Crocker Highlands

🌟 Spacious suite located in one of the most scenic & safest communities in Oakland / Piedmont / Berkeley. Dog friendly. Up to 4 guests. Well suited for remote working. Nestled amongst stately homes and walkable tree-lined streets. Perfect retreat from exploring San Francisco, wine country or family. Level entrance. Suite is located on the lower story. We live above and as we are very conscientious of our guests, you may hear the pitter-patter of home life above.