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4,355 Oakland Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Oakland holiday rentals from 15 rental sites including Booking.com, HomeAway, TripAdvisor, and more, ranging from $25 to $4000 a night. 
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    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

    Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Oakland offers 4,370 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $248 a night, or a long-term rental for an average price of $5837 a month.

    These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 1,889 of Oakland’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 105 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 3,199 cozy homes.

    Traveling with pets? Choose from 348 pet-friendly rentals in Oakland for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

    Search properties from 15 rental sites in Oakland where the top providers in that area are Booking.com, HomeAway, and TripAdvisor. There are 2,012 Booking.com rentals, 970 HomeAway short term rentals and 707 TripAdvisor vacation rentals.