Family-friendly holiday rentals 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?

Beautiful canyon view suite

Enjoy Shepherd Canyon: sunlight dancing on leaves, birds flying at eye level, sun setting behind eucalyptus trees, flickering lights at night. Downstairs floor (1100 sq ft) of mid-century home in Oaklands Hills. Full kitchen for snacks or gourmet meals, comfy queen bed in bedroom, sofa bed in living room. Enjoy picturesque walk to Montclair Village or hike/ bike right up the hill. Drive 11 minutes to BART, located in Rockridge, which also has restaurants and shops to explore. Minimum age 25

Charming in-law retreat w/patio & scenic garden

Located in Oakland's scenic lower hills, the Airbnb is the downstairs of our house. It includes 1 spacious bedroom w/desk, a smaller bedroom with a double bed, & tv, a full bathroom, kitchen, & a small dining area. The private entrance from the back patio looks out over a spacious yard. Our neighborhood has tall trees, expansive green space, and is quiet, friendly & safe. A few minutes from Park Blvd.'s and Montclair's many cafes, it's even closer to the Dimond district's eateries & markets.

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.

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

BridgesView Spa & Couples Retreat, Easy Parking

This luxurious suite with kitchenette features a beautiful view towards the Bay and Golden Gate Bridges, designed especially for a romantic getaway or anyone needing a relaxing space. Soak and play in the two-person jetted tub, enjoy the gorgeous large bathroom. Easy street parking is always available, and garden lined exterior stairs take you to the private entry and patio. A laundry is provided for guest use only. Hikes into the canyon below or neighborhood above are a special treat.

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.

Private Mid-Century Modern With Fabulous Garden

Thoroughly renovated and private mid-century modern suite in a side-by-side duplex. Secluded backyard w/ patio & bbq. Fully equipped chef’s kitchen & spa-like bathroom. Please note - we removed the heat lamp from the backyard due to safety concerns. Photos of the yard including the lamp will be updated as soon as possible. -96 Walk Score -30 minutes to downtown San Francisco -40 minutes to several beaches -1.5 hour to Napa Valley -3 hours to Lake Tahoe

Tiny Home | Walker's Paradise 98/100 | Big Style

Discover a unique Oakland gem! Our brand-new tiny home, nestled in a shipping container, offers all the essentials in a smart, space-saving design. Perfect for the solo adventurer, this cozy retreat is in a prime location with a walkability score of 98/100. Immerse yourself in a walker's paradise, ideal for those traveling light. Experience tiny living in a big way! **Please note:This space is best suited for solo travelers who travels light**

Silk Meets Sakura · Private Suite + Shoji Bath

Newly remodeled (2026): now a fully private suite with independent entrance and ryokan-style spa bath. A Silk Road journey from Marrakech to Kyoto in the Oakland Hills — Moroccan lanterns, Turkish textiles, and Afghan Majilis-style floor seating meet a Japanese-minimalist king bedroom. — 10 min to BART & Coliseum — 15 min to OAK & downtown Oakland — 25 min to downtown SF — 35 min to SFO Weekly stays welcome with discounts.

A Midcentury's Night Dream- Oakland

Welcome to Fabulous Lake Merritt and the Haddon Hill/Cleveland Heights neighborhood, your gateway to Oakland, Berkeley, SF and beyond. This sunny one bedroom, one bathroom duplex apartment was built in 1955 and is mid-century modern in style with modern conveniences. Here you can enjoy vintage decor that doesn't take itself too seriously; think Don Draper meets Howdy Doody. A vibrant, yet relaxing, place to stay!