Destination guide

It’s all happening in old Oakland

A magnet for bohemians, beatniks, and young entrepreneurs, Oakland is the happy little brother of San Francisco. Travelers often miss out on its charms thanks to the famous draws of the West Bay Area, but that's a huge shame. You can wallow here between Pacific brew pubs and independent coffee roasters, explore an ethnically diverse Chinatown, or unravel fascinating stories in the African American museum. Science centers, quirky art galleries, and access to the famous Napa Valley all add to the draws, while Oakland vacation rentals are affordable and stylish to boot.

Things to do

Local history and local wine in Oakland

Whether you bag a rustic cabin in the Oakland Hills for all that hiking and wine tasting in the world-famous Napa Valley, or opt for Oakland vacation rentals in the heart of the town where there are attractions like the classic Fox Theatre and the Children's Fairyland theme park, you can rest assured there's something for everyone in this corner of the Bay Area. And that's not even mentioning the acclaimed elephant enclosures at Oakland Zoo, the immersive Oakland Museum of California, and the intrepid trails of the Redwood Regional Park.


Oakland offers laid-back Bay Area life

Without the stresses of big San Francisco, Oakland manages to create a more chilled and accessible vibe. Regular walking tours of districts like Old Oakland and the 1920s grandeur of Uptown take place most days of the week, and they are neatly balanced out by beer tasting sessions or opportunities to craft your own ales in the town's wealth of cool breweries. Cycling and hiking in the surrounding Oakland Hills is also a great way to survey the beautiful Californian backcountry, while regular farmers' markets and local craft fares are on the calendar all throughout the summer.


Dodge the Pacific rains and winter in Oakland

The months between May and August are virtually without rain in this part of the Bay Area, which makes the summer the perfect time to search for Oakland vacation rentals, especially if you're planning on hiking the Oakland Hills and enjoying the town's top al fresco bars. There's also usually an Indian Summer in these parts, with September and October not only having high temperatures but also some cheaper places to stay. And coming then will mean you dodge the regular downpours of the winter between December and March.

Natural features

Surrounded by the Oakland Hills

Oakland sits sandwiched between the scrub-dressed hills and the coastal flats of the San Francisco Bay Area. The swaying trees of the Redwood Regional Park ensconce the city to the east, offering a glimpse at northern Cali's ancient forestry. That soon gives way to the secluded Siesta Valley, which has undulating hills of meadow and scrub, and the De Laveaga Trail that weaves past curious rock formations. Topping off the lot is the lofty Wildcat Canyon Regional Park, where the foxglove fields peak and trough over scrubland that's peppered with snakes and horned owls.

How to get there

Transportation to and around Oakland

Fly into Oakland, CA (OAK-Oakland Intl.), the closest airport, located 7.1 mi (11.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Hayward, CA (HWD-Hayward Executive), which is 13 mi (20.9 km) away.

If you're traveling by train, make your way to Oakland-Jack London Square Station or Coliseum Station to see more of the city. You can get around Oakland by catching a ride on the metro at 12th St - Oakland City Center Station, 19th St Station or Lake Merritt Station.

Can I find a vacation rental around Oakland?

Yes, our 2019 property listings offer a large selection of 1,702 vacation rentals near Oakland. From 577 Houses to 864 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Oakland for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Oakland?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Oakland:

  • Rockridge: 137 vacation rentals
  • Forestland: 22 vacation rentals
  • Lake Merritt: 56 vacation rentals
  • Temescal: 29 vacation rentals
  • Piedmont Pines: 24 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Oakland?

HomeAway offers a large selection of vacation rentals near lovely places in Oakland. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Jack London Square: 2,198 vacation rentals
  • Lake Merritt: 2,168 vacation rentals
  • East Bay Regional Park District: 1,940 vacation rentals
  • Coliseum: 2,065 vacation rentals
  • Oakland City Center: 2,181 vacation rentals

But there are many other points of interest around Oakland listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Oakland?

Yes, of course. HomeAway has 577 Houses in Oakland. Our other popular types of vacation rentals in Oakland include:

  • Condos/Apartments: 864 rentals available
  • Cottages: 48 rentals available
  • Studios: 764 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Oakland?

Yes, you can select your preferred vacation rental with pool among our 174 vacation rentals with pool available in Oakland. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Oakland

    San Francisco
    1,891 vacation rentals
    937 vacation rentals
    Stinson Beach
    438 vacation rentals
    San Jose
    895 vacation rentals
    1,463 vacation rentals
    Half Moon Bay
    456 vacation rentals
    1,642 vacation rentals
    Palo Alto
    588 vacation rentals
    Mill Valley
    1,371 vacation rentals
    1,030 vacation rentals
    Mountain View
    794 vacation rentals
    San Rafael
    555 vacation rentals
    1,181 vacation rentals
    Walnut Creek
    1,519 vacation rentals
    868 vacation rentals
    San Mateo
    1,704 vacation rentals
    1,302 vacation rentals
    702 vacation rentals
    Redwood City
    593 vacation rentals
    Muir Beach
    1,411 vacation rentals