Holiday rentals in Oakland

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Top-rated holiday rentals in Oakland

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Guest favourite

Cottage in North Oakland

4.91 out of 5 average rating, 420 reviews

Magical Modern Cottage with Garden

Find true escape surrounded by nature at this lovely modern cottage. Once featured in Dwell magazine, this home charms with its clever use of space, custom furniture and finishes, unique and tasteful decor, and outdoor patio and garden. Entire private cottage and shared side and backyard with patio seating. We are happy to suggest hikes, restaurants and other activities. We've compiled an extensive list of our favorite spots, both right in the neighborhood and also farther afield. The property is located in Rockridge, and also quite close to Temescal. Both have lots of great shopping, restaurants, coffee shops, and amenities. We are very pleasant 10-15 minute walk from the Rockridge BART station. BART provides easy access to SF (about 20 min) and other parts of the Bay Area. Parking on our street is free and usually plentiful. Street sweeping is on the second and fourth Monday/Tuesday of each month (check signs to be sure). The bedroom of the cottage is located up a short flight of stairs, so it isn't ideal for anyone with compromised mobility. The bathroom shower is fully functional but some particularly large/tall people may find it a little tight.

Guest favourite

Guest suite in Oakland

4.97 out of 5 average rating, 388 reviews

BridgesView Spa & Couples Retreat, Easy Parking

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

Guest favourite

Rental unit in Oakland

4.99 out of 5 average rating, 251 reviews

Modern retreat in the tree tops

Relax in this tranquil space nestled in Oakland Hills. Private inlaw unit furnished with modern furniture and art. Kitchen replete w/microwave-convection oven, induction cooktop, dishwasher, coffeemaker, prep tools and serving items await. Enjoy the electric fireplace, cable TV and high-speed WiFi. Stylish bathroom and comfy bed to refresh and relax. From the off-street parking spot, take the 30 well-lit and stable stairs to this quiet home away from home. No pets or smoking on premises. Enjoy!

Guest favourite

Guest suite in North Oakland

4.98 out of 5 average rating, 743 reviews

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

Cozy, clean studio 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! Easy 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.

Guest favourite

Guest suite in Temescal

4.97 out of 5 average rating, 273 reviews

Light Filled in the Heart of Temescal’s Jewel Box.

Welcome to the quiet Temescal Jewelbox! Newly renovated, our backyard apartment is a home away from home in one of Oakland’s most vibrant centrally located neighborhoods. We love Temescal! Fully equipped new kitchen, a light filled living area with our prize 1957 Metz music cabinet, restored and Bluetooth compatible - stream your play lists from the dedicated WiFi. Settle in to the upstairs bedroom with a cozy reading nook, desk space, a “walk-up” closet, en-suite small bathroom with shower.

Guest favourite

Guest suite in Oakland

4.97 out of 5 average rating, 181 reviews

Curated Studio w/ Hot Tub & Outdoor Bath

Stay in a modern space curated by Oakland artists! This spacious studio features reclaimed barn wood throughout with eclectic modern furnishings. Snuggle up in the queen sized Casper mattress with luxurious spa quality sheets. Working while traveling? We've got gigabit wi-fi. Couples will enjoy the garden hot tub & outdoor bath with dual shower heads. Just looking to relax? Take a dip in our private outdoor bathing tub. Gated off-street parking & anytime contactless checkin are included too!

Guest favourite

Guest house in North Oakland

4.98 out of 5 average rating, 291 reviews

Modern, bright Rockridge studio with patio.

Recently renovated modern studio apartment, with lots of light and an open layout featuring full kitchen, dishwasher, and washer/dryer in the unit. Designed as a luxury cottage for family visits, this cozy space feels very open, with skylights and French doors that open onto a patio with seating and gas grill. Quiet and private - the entrance is at the end of a long driveway - and ideally located within easy walking distance of BART, bus routes, College Ave and 24 to the Bay Bridge.

Guest favourite

Guest house in Oakland

4.93 out of 5 average rating, 255 reviews

Private, Detached, Urban Creekside Studio.

This unique, well equipped, 1 Bed cute little studio (that we love) is detached and fenced off from our main house. It has a separate entrance through a side gate and it's own private rear deck, with a seating and dining area... that overlooks Sausal Creek and Dimond Park. The tall willow that grows along the creek gives the deck the perfect amount of privacy and with the tranquil sound of the creek flowing (not during dry season) you would almost forget you are in an urban city.

Guest favourite

Guest suite in Temescal

4.98 out of 5 average rating, 301 reviews

Garden View Victorian Apt. in Temescal w/ Hot Tub

Sunny garden view 1 bedroom suite in craftsman style home w/ hot tub. This is a separate unit, with complete privacy. Quiet neighborhood, walk to many restaurants ,shops, & coffee houses. Separate garden entrance. Private full bath w/ shower/tub. Bedroom w/ queen bed & TV,( Hulu). Kitchenette/sitting room includes a microwave, blender, refrigerator, two gas burner cook-top, toaster oven . Kitchen is stocked w/ basics, elec. tea kettle and coffeemaker. Off street parking. AC

Guest favourite

Guest house in Grand Lake

4.98 out of 5 average rating, 454 reviews

Garden cottage in convenient Oakland location.

You’ll love my place because of the good location, convenience to public transport, the friendly neighborhood, the ambiance.. My place is good for couples, solo adventurers, business travelers, and families (with kids). Although there is just one bedroom, the couch folds down for extra sleeping space. Please be aware that the property is in a hilly area and that there are stairs to navigate which can be challenging if you have large luggage or mobility issues.

Guest favourite

Home in Eastmont Hills

4.97 out of 5 average rating, 587 reviews

Private Casita with Stunning View

Relax in a private, fully equipped Casita with stunning views of East Oakland and the Bay. This newly constructed one-bedroom guest house in the quiet Eastmont Hills neighborhood has everything you need to work and play. Enjoy lounging in a hammock on the deck or on the couch streaming movies to a 32" television. Brand new stainless steel gas range and full-sized fridge make cooking a breeze, or you can partake in booming Oakland's restaurant scene.

Guest favourite

Rental unit in Oakland

4.97 out of 5 average rating, 251 reviews

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!