Family-friendly holiday rentals in Oakland

Classic Bright Modern Spacious 1bd/1ba Apartment

Quiet & spacious 960 sq ft modern, bright one-bedroom apartment with wireless high-speed internet. This private & newly renovated open floor plan & chef's kitchen with stainless steel appliances is ideal for long stays. The apartment features a sunny deck off the kitchen and backyard for dining or relaxing. Centrally located in a tree-lined walkable neighborhood. UC Berkeley and BART in short distance. Drink your morning coffee on a sun-drenched deck and at night cozy up by the indoor fireplace.

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.

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

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.

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

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.

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.

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!

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.