Holiday houses in Oakland

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Top-rated holiday rentals in Oakland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in North Oakland

4.96 out of 5 average rating, 100 reviews

7-30 Days Modern Garden Guesthouse, Step-Free

New build, all one level, no steps to entrance from street. Private quiet dedicated guesthouse. Plentiful, free street parking w/in one block. Keyless entry. 450 sq ft but feels larger. Queen bed, large closet, full kitchen, large bathroom, private patio. Free W/D. 2-55" TVs with digital antennae +Roku. Kitchen table doubles as desk. No cleaning fee. Our family plays in shared yard late afternoon with 2 friendly dogs. 7-30 days firm per business license. For two guests, choose "2" when booking.

30 Apr – 7 May

$237 NZD per night

Guest favourite

Guesthouse in Oakland

4.93 out of 5 average rating, 427 reviews

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!

19–26 Jun

$272 NZD per night

Guest favourite

Guesthouse in Temescal

4.85 out of 5 average rating, 278 reviews

Rockridge Garden Cottage

The cottage is newly remodeled as of March 2022 and now has its own kitchen and bathroom. It is a separate unit in my backyard with vaulted ceilings which gives a spacious feel and french doors that open onto the lush garden. Queen size high end natural organic fiber bed (Earthsake.com), with down comforter + 4 pillows. Dining table and stools. LCD TV, clothes valet, work desk and great internet. Its very quiet and my guests seem to love having a private retreat type space to themselves.

31 Jul – 7 Aug

$273 NZD per night

Guest favourite

Guest suite in North Oakland

4.98 out of 5 average rating, 672 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.

14–21 Jul

$215 NZD per night

Guest favourite

Guest suite in Temescal

4.97 out of 5 average rating, 244 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.

14–21 Oct

$272 NZD per night

Guest favourite

Guest suite in Oakland

4.96 out of 5 average rating, 359 reviews

Serene and comfortable 1 bedroom apt

Welcome to our 1 bedroom Airbnb with a separate private entrance situated on the ground floor of a three level house. This airbnb comfortably sleeps 2 people with access to a large deck. The house is located in the Oakland hills in an upscale neighborhood with a beautiful serene canyon as your back drop. It is centrally located approximately 20 minutes to all nearby cities; San Francisco Berkeley, Walnut Creek, Hayward and the Oakland Airport (during non-commute hours).

7–14 Jul

$234 NZD per night

Guest favourite

Guesthouse in Oakland

4.96 out of 5 average rating, 181 reviews

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 city. The cottage is at the back of our large garden with views of our beautiful urban farm with a pond with croaking frogs, chickens and goats! Couples and families with up to 2 children are best suited for this space. No more than 2 adults please.

25 Aug – 1 Sep

$210 NZD per night

Guest favourite

Guesthouse in Oakland

4.92 out of 5 average rating, 249 reviews

Guesthouse Garden Retreat

Our 'sister guesthouses' consist of two small side-by-side cabins (you get both) located behind our home, nestled in a verdant hillside garden that our friends and family lovingly call ‘Little Tuscany’. Cabin 1 - living room with a well-stocked kitchenette, pull-out couch, table and chairs Cabin 2 - bedroom with a queen-size bed, full bathroom and a private deck Accessed by a private entrance, the cabins are luminous and efficient, designed to meet all your needs.

25 Jun – 2 Jul

$223 NZD per night

Guest favourite

Guesthouse in Oakland

4.98 out of 5 average rating, 428 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.

26 Mar – 2 Apr

$149 NZD per night

Guest favourite

Home in Eastmont Hills

4.98 out of 5 average rating, 530 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.

7–14 Dec

$168 NZD per night

Guest favourite

Cottage in Oakland

4.99 out of 5 average rating, 177 reviews

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.

1–8 Sep

$260 NZD per night

Guest favourite

Guesthouse in Oakland

4.96 out of 5 average rating, 488 reviews

Lakeshore Cottage

Our quiet studio cottage is located in the Lakeshore/Grand Ave area of Oakland. The neighborhood is safe and beautiful and the cottage is neat and easily accessible. There is a large bright main room and a spacious bathroom that was recently updated. The cottage includes a mini kitchen. The location is close to downtown Oakland, Berkeley and San Francisco.

10–17 Sep

$202 NZD per night