849 Oakland Holiday Rentals

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Compare Oakland holiday rentals from 15 rental sites including Booking.com, HomeAway, TripAdvisor and more, ranging from $25 to $12500 a night.

Information about Oakland

About Oakland

Oakland, a large port city in the San Francisco Bay Area, is known for its industrial history and rich diversity. Shortly after incorporation, Oakland became the western terminal of the Transcontinental Railroad. Its legacy as a leader in technology continued with the tech industry and manufacturing. Oakland also has a strong reputation for its political activism. Though it was formerly known for racial tension and crime, it has recently experienced a renaissance. Several landmarks have undergone significant improvements, and there are many local spots that are easier on your wallet than nearby San Francisco attractions. Whether you’re looking for rich cultural history or vibrant city life, you’re sure to find something to love in Oakland.

Things to do in Oakland

Sports fans can choose from many Bay Area franchises to see in Oakland. See the Raiders compete in an NFL game or head to the Coliseum to see the A’s play. While Giants games are often very costly in San Francisco, some A’s tickets are as cheap as two dollars! Basketball fans can also check out Oracle Arena, the home of the Golden State Warriors.

For a reprieve from the hustle and bustle of Oakland, escape to Redwood Regional Park. There are hiking and biking trails, and many areas are dog-friendly. Though it feels far away from the city, it is only ten miles from Oakland.

Day Trips from Oakland

Though San Francisco is too large to see in one day, its innumerable attractions and proximity to Oakland make it a must-see city. Many parks dot the urban landscape and offer stunning views of the city, such as Grand View Park, which rewards travelers with a 360-degree panorama of San Francisco. There are also citywide events—such as music festivals, art exhibitions, and historical celebrations—happening nearly every weekend.

An hour-and-a-half north of Oakland, Napa Valley provides travelers with world-class wine and relaxation. Tour some of its many wineries via bike or limousine tour and see why Cabernet Sauvignon reigns supreme in this region. For those who would prefer to skip the drive, there is a shuttle from the Oakland Airport to Napa Valley.

Out-of-state visitors may be inclined to make the 3.5-hour trek to Lake Tahoe. If so, travelers will be enchanted by stunning mountain views and sapphire-blue water. In the summer, there are many opportunities for hiking and camping. During the snowy months, outdoorsy types have the chance to ski or snowboard at world-class resorts, such as Heavenly and Northstar.

Oakland Accommodations

There are nearly 1,000 vacation rentals available on Tripping.com. Many properties are near public transportation, which allow for convenient travel within Oakland, San Francisco, and the rest of the Bay Area. Try to stay near downtown Oakland, Lake Merritt, or in the Rockridge neighborhood for the closest access to cute shops and excellent restaurants.

Transportation in Oakland

Oakland International Airport is located five miles south of the city and is serviced by most major airlines. It is accessible by car on I-580 from the north and south and I-80 from the east and west. Once you arrive, Oakland is part of an extensive public transportation system called BART, which offers transportation within the city as well as other Bay Area destinations.

Vacation Rentals in Oakland

Find the best Oakland vacation rentals with Tripping.com. Choose from 5053 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $12500 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 2481 of homes in Oakland offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 140 rentals with pool or jacuzzi, or relax with the family in one of the 3375 homes with cable TV.

For all those dog lovers and cat lovers, Oakland offers 366 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 15 rental sites in Oakland where the top providers in that area are Booking.com, HomeAway, and TripAdvisor. There are 2056 Booking.com rentals, 1422 HomeAway short term rentals and 671 TripAdvisor vacation rentals.
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