Oakland vacation rentals

We found 178 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Oakland that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation homes have the amenities you need and want for your stay, which might include WiFi and a washer and dryer, No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including accessible or non-smoking choices.
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
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Find out more about Oakland

Find out more about Oakland

Why visit Oakland

  1. Cultural richness: Explore diverse attractions, including modern colleges, arts centres, and entertainment venues.
  2. Scenic views: Enjoy breathtaking vistas from the Oakland Hills and picturesque waterfront settings.
  3. Vibrant neighbourhoods: Discover West Oakland, known for its thriving arts scene and friendly atmosphere.
  4. Family-friendly activities: Engage in enriching experiences suitable for all ages, perfect for family vacations.
  5. Varied accommodations: Choose from cozy vacation homes, modern apartments, and charming cottages to fit your needs.

Popular types of accommodation around Oakland

Planning a getaway to Oakland? Discover the charm of this vibrant city by choosing from a variety of vacation rentals. From cozy houses and modern apartments to quaint cottages, you'll find the perfect accommodation to suit your needs. With numerous options for vacation homes in Oakland, enjoy transparency and savings while exploring all that this beautiful destination has to offer. Start your adventure with the best rentals in Oakland today!

  • Houses: Our top choice for visitors to Oakland, these homes offer a comfortable and spacious environment perfect for families or groups.
  • Apartments: A popular option for those seeking convenience, these rentals provide a blend of comfort and accessibility in the heart of the city.
  • Cottages: These quaint accommodations offer a cozy atmosphere, ideal for a peaceful getaway.
  • Condos: A stylish option, condos combine modern amenities with a central location.
  • Cabins: For nature enthusiasts, cabins provide a charming retreat surrounded by the great outdoors.**

Top attractions around Oakland

Oakland, Pittsburgh, is a vibrant destination perfect for city-themed, cultural, and family vacations. Visitors can explore a range of attractions, including modern colleges and universities, entertainment arenas, and arts centres. This lively neighbourhood caters to those seeking enriching experiences, making it an ideal spot for tourists. Don't miss the chance to discover the unique local culture and engaging activities that Oakland has to offer during your visit.

  1. University of Pittsburgh: A vibrant modern university nestled in Oakland, offering a dynamic atmosphere with stunning architecture and a rich cultural scene. Visitors can explore its beautiful campus and experience the youthful energy of its diverse student body.
  2. PPG Paints Arena: Located 3.2km from Oakland, this arena is a hub for family-friendly entertainment, hosting thrilling sports events and concerts. The lively atmosphere and variety of activities make it a great spot for all ages.
  3. David L Lawrence Convention Center: Situated 3.2km from Oakland, this state-of-the-art convention centre is designed for business events, showcasing impressive architecture and spacious meeting rooms, ideal for conferences and exhibitions.

Things to do recommended for couples

For a romantic getaway in Oakland, don't miss the breathtaking views from the Duquesne Incline, just 4.8km away. Enjoy a concert at the Rex Theater, 3.2km away, or indulge in luxury at the Oakmont Country Club, located 14.5km from your base. Perfect for couples!

Things to do recommended for families

Your family will love Oakland, Pittsburgh! Experience the excitement at Acrisure Stadium, relax in the beautiful Schenley Park, and dive into fun at Sandcastle Water Park. Each destination offers unique vibes, making your visit memorable and enjoyable for everyone!

Things to do recommended for groups

Explore Station Square for shopping and entertainment, only 3.2km from Oakland. Enjoy a cultural experience at the Pittsburgh Playhouse, located nearby, or visit Bicycle Heaven, a unique store 6.4km away, perfect for group adventures.

What do I need to keep in mind when booking a vacation around Oakland

If you're travelling with a group, family, or pets, or if you're considering a longer stay, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Oakland with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Oakland with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Oakland: For many families, a getaway isn’t truly fulfilling without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that all members of the family feel comfortable and at ease.
  • Planning for a long term stay visiting Oakland: If you’re searching for vacation rentals that offer discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search for the perfect getaway.

Where to stay around Oakland

Oakland, Pittsburgh, offers a delightful mix of urban charm and family-friendly vibes. Explore the picturesque waterfront and enjoy the scenic lakeside setting, while the Oakland Hills provide stunning views. Don’t miss West Oakland, where art and community thrive. This vibrant neighborhood invites you to experience its friendly atmosphere, making it an ideal destination for culture enthusiasts and families alike. Your vacation in Oakland promises a unique blend of experiences and unforgettable memories.

  • Downtown Pittsburgh: Located 3.2km from Oakland, Downtown Pittsburgh is the vibrant core of the city, where family-friendly activities, sports events, and urban experiences await. Visitors can explore an array of attractions, including the impressive PPG Paints Arena and the bustling shopping district. Don’t miss the iconic Heinz Field and PNC Park, where thrilling sports events take place. The nearby urban parks provide a serene escape from the city hustle, making it a perfect spot for both relaxation and adventure.
  • North Oakland: Just 805m away from Oakland, North Oakland is a culturally rich neighbourhood ideal for families and city explorers. This area boasts top-notch educational institutions, including modern colleges, and lively sports venues. The local golf courses and arena entertainment facilities offer a diverse range of activities. With its close proximity to stadiums, North Oakland provides easy access to exciting sporting events, making it a must-visit for sports enthusiasts and culture seekers alike.
  • Central Oakland: Also located 805m from Oakland, Central Oakland is a hub of culture and family experiences. The neighbourhood features educational institutions and recreational areas that cater to all ages. Visitors can enjoy arena entertainment and explore the local parks, perfect for outdoor activities. With its proximity to modern universities and sports facilities, Central Oakland offers an engaging atmosphere for those looking to immerse themselves in the local culture while enjoying a lively community vibe.

Best time to go to Oakland

If you're planning a trip to Oakland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like May and November to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January28.6°F (-1.9°C)Light RainMostly CloudyAverageSlightly Low
February31.3°F (-0.4°C)Light RainMostly CloudyAverageSlightly Low
March40.5°F (4.7°C)Light RainMostly CloudyAverageSlightly Low
April51.1°F (10.6°C)Light RainMostly CloudySlightly HighAverage
May61.7°F (16.5°C)Light RainMostly SunnySlightly LowAverage
June69.4°F (20.8°C)Light RainMostly SunnyAverageSlightly High
July73.9°F (23.3°C)Light RainMostly SunnySlightly HighAverage
August72.1°F (22.3°C)Light RainMostly SunnyAverageAverage
September66.2°F (19.0°C)Light RainMostly SunnySlightly HighAverage
October54.7°F (12.6°C)Light RainMostly SunnyAverageSlightly High
November42.6°F (5.9°C)Light RainMostly SunnySlightly LowSlightly High
December35.2°F (1.8°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? One way to do this is by being flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform to plan new vacations, resume previous arrangements, or manage your travel itinerary. You can easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply head over to: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Oakland?
Apartments are the most popular style of vacation rental in Oakland, according to our data. Even if you have something different in mind, Vrbo has properties in many sizes and shapes. Browse our options to find your perfect match.
How much does it cost to rent a vacation rental in Oakland?
A range of factors influence how much you’ll pay for a vacation rental in Oakland, including the season, type of property and length of stay. Still, all our vacation homes have one thing in common — unbeatable value. Just add your travel dates to find your perfect match.
How much does it cost to rent a beach house in Oakland?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Type in your Oakland travel dates to view your options on Vrbo. Can’t live without a hot tub, or maybe a private pool? Use our filters to pick the features and amenities you want.
Are there pet-friendly vacation rentals in Oakland?
Yes. You can pick from 21 vacation rentals that cater to pets in Oakland. Several of our pet-friendly vacation rentals come with an outdoor area for your fur child to run around in, complimentary treats, doggie beds and proximity to parks and green space. Apply the “Pets allowed” filter to find your pawfect pad on Vrbo.
What are popular rental amenities in Oakland?
The most popular rental amenities people search for in Oakland are a nearby river, a barbecue grill and a garden. Whether you’re going on vacation with your besties, family or even pets, Vrbo vacation homes provide the best amenities for making epic memories with the people who matter most.
Are there large group vacation rentals in Oakland?
You can pick from two vacation rentals in Oakland that can accommodate 10 or more guests. Whether you’re planning a family vacation or a special event like a birthday party, there’s ample room to get your favorite people together under the same roof.
Are there vacation rentals in Oakland that welcome kids?
With 21 family-friendly vacation rentals to select from in Oakland, now is a fantastic time to introduce your children to the magic of travel. Check our “Properties good for families” filter box to search for stays loaded with amenities perfect for traveling families, such as kitchens, yards, bunk beds and entertainment units.
What are the top attractions for families in Oakland?
Keep the kids amused at these popular family-friendly attractions in Oakland:

  • Pittsburgh Zoo and PPG Aquarium
  • Carnegie Science Center
  • Carnegie Museum of Natural History

Are there one-bedroom vacation rentals in Oakland?
There are seven one-bedroom properties in Oakland to choose from. A one-bedroom vacation rental is a great option if it’s only you and your partner or if you’re vacationing solo. Add in more space, privacy and convenience than a standard hotel, and you’ve got the makings of an unforgettable break.
Can I find two-bedroom vacation rentals in Oakland?
Oakland has eight two-bedroom properties to select from. Go for a vacation home with all the space and privacy you need at a fantastic price on Vrbo.
How can I find vacation rentals with air conditioning in Oakland?
Oakland has 21 vacation rentals where you’ll be able to relax and recharge in air-conditioned comfort. To find a property on Vrbo that comes with this amenity, enter your travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Oakland?
The minimum age allowed can differ between properties on Vrbo, so be sure to look at the rules of the vacation home in Oakland you want. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Oakland for?
The amount of time you can book an Oakland vacation rental for varies depending on the property. Just enter your travel dates to browse available options that offer long-term stays. They come with all the things you need to make your extended break more enjoyable and comfortable, like kitchens and backyards. Some vacation rentals may also offer discounted weekly or monthly prices, so you can stay longer for less money.

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