Oakland holiday homes

We found 173 holiday rentals — enter your dates for availability

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July 2025

August 2025

Discover a selection of 7 homes and other holiday rentals in Oakland that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for spending time at your holiday home, which might include a garden and pool. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Oakland

Showing deals for:24 Oct - 31 Oct

Exceptional

(21 reviews)

Best skyline view of CMU/PITT Historical Oakland 5BR storybook house 3000sf

Pittsburgh, PA

8% off

NZ$1,115 per night

includes taxes & fees

Exceptional

(11 reviews)

New Loft 3 min to CMU, Pitt Sleeps 4

Pittsburgh, Pennsylvania

8% off

NZ$354 per night

includes taxes & fees

Exceptional

(16 reviews)

Amazingly Homey w/Garage + Outdoor Space! 5B/2B

Pittsburgh, PA

7% off

NZ$1,284 per night

includes taxes & fees

Wonderful

(5 reviews)

Carey Way Quarters-Stylish 3BR Loft-Prime Location

Pittsburgh, Pennsylvania

10% off

NZ$411 per night

includes taxes & fees

Exceptional

(16 reviews)

PGH Jewel - Modern All New 5B/5B, Near Downtown, Private Parking

Pittsburgh, PA

8% off

NZ$1,322 per night

includes taxes & fees

Very good

(5 reviews)

Modern & Spacious minutes from town, UPMC Hospitals, Universities & PPG Arena!

Pittsburgh, PA

8% off

NZ$406 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Find properties near top attractions in Oakland

University of Pittsburgh

Carnegie Museum of Natural History

Carnegie Museum of Art

Soldiers and Sailors Memorial Hall and Museum

Heinz Memorial Chapel

Find the best place to stay - Oakland

Cozy home close to UPMC/CMU/UPITT/DUQSNE/CARLW Minutes from everything w/Parking

Sleeps 6 · 3 bedrooms · 2 bathrooms

Elevator~West Penn~Parking~Queen Bed-Central Location

Sleeps 3 · 1 bedroom · 1 bathroom

Master suite with private full bath and balcony overlooking Southside and city!

Gorgeous Southside Slopes home with outdoor hot tub and city view!

Sleeps 13 · 4 bedrooms · 2+ bathrooms

Kasa South Side Pittsburgh

Sleeps 5 · 2 bedrooms

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Oakland?

Apartments are the most popular style of holiday home in Oakland, according to our data. Even if you have something different in mind, Bookabach has properties in many sizes and shapes. Browse our options to find your perfect match.

How much does it cost to rent a holiday home in Oakland?

A range of factors influence how much you'll pay for a holiday home in Oakland, including the season, type of property and length of stay. Still, all our holiday 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 Bookabach. 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 holiday homes in Oakland?

Yes. You can pick from 21 holiday homes that cater to pets in Oakland. Several of our pet-friendly holiday homes 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 Bookabach.

What are popular home amenities in Oakland?

The most popular home amenities people search for in Oakland are a nearby river, a barbecue grill and a garden. Whether you're going on holiday with your besties, family or even pets, Bookabach holiday homes provide the best amenities for making epic memories with the people who matter most.

Are there large group holiday homes in Oakland?

You can pick from two holiday homes in Oakland that can accommodate 10 or more guests. Whether you're planning a family holiday or a special event like a birthday party, there's ample room to get your favourite people together under the same roof.

Are there holiday homes in Oakland that welcome kids?

With 21 family-friendly holiday homes 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 travelling 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 Centre
Carnegie Museum of Natural History

Are there one-bedroom holiday homes in Oakland?

There are seven one-bedroom properties in Oakland to choose from. A one-bedroom holiday home is a great option if it's only you and your partner or if you're holidaying 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 holiday homes in Oakland?

Oakland has eight two-bedroom properties to select from. Go for a holiday home with all the space and privacy you need at a fantastic price on Bookabach.

How can I find holiday homes with air conditioning in Oakland?

Oakland has 21 holiday homes where you'll be able to relax and recharge in air-conditioned comfort. To find a property on Bookabach 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 holiday home in Oakland?

The minimum age allowed can differ between properties on Bookabach, so be sure to look at the rules of the holiday home in Oakland you want. But typically, it's 16, 18 or 21.

How long can I rent a holiday home in Oakland for?

The amount of time you can book an Oakland holiday home 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 holiday homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.