Family-friendly holiday rentals in Oakland

Eco-Cottage Sanctuary in Garden Oasis

Our popular cottage is like a retreat experience in the city! The cottage is an enchanting oasis nestled in the back and away from street noise. You will sleep comfortably on our new mattress topper! Our urban farm and garden offers a unique heartwarming experience-with lush gardens, chickens and goats! The cottage is perfect for guests looking for a comfortable space to relax after a busy day. Come and enjoy our beautiful and relaxing eco-friendly cottage! Family friendly. Only 2 adults please.

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?

5 Bedroom home with bay views for large groups

Spanish-style home in the Oakland hills , a quiet neighborhood Spacious, open layout with fantastic views of the San Francisco Bay Area. Great location: Close to Montclair village and quick access to San Francisco. Half-mile walk to the best open space parks in the east bay: Joaquin Miller Park! Features one acre of attractive gardens, patios, and a large deck with bay views. Great for family reunions, get-togethers or larger families. Plenty of parking, 4 cars+, in huge private driveway

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.

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.

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

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 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**

The Cozy Casita 2

Welcome to the Cozy Casita, you’re home away from home. The central location makes it the perfect jumping off point for all your Bay Area adventures with close proximity to MacArthur BART station, Multiple bus stops, Bay Wheels bike rental, shops and restaurants in Emeryville and Temescal, Access to 4 major highways within 1/4 mile, Lake Merritt, Uptown/Downtown Oakland, San Francisco, Berkeley, and many more Bay Area hotspots.

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!