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.

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

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.

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

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.

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.

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.

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!

Trixie's Studio Garden Cottage

We have a lovely private garden cottage available in a quiet Oakland neighborhood, very close to Lake Merritt. Shopping, restaurants, and cafe's are a 10 minute walk away. Cozy furnished, sound proofed studio with blackout windows, thermal heated flooring, small kitchen, bath & living area. Free high speed internet, security & housekeeping service. Ample street parking and very close to public transportation.