Discover a selection of 27 vacation rentals in Oakland, Pittsburgh that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $23 per night, and houses and condos are popular options for a stay in Oakland. Either way, you'll find a rental for everyone's needs.
Destination guide

Head to the friendly city of Oakland

Enjoy the area's cathedral, museums and architecture and make a vacation rental your home during your stay in Oakland. Well known for its university setting, restaurants and sporting events, this welcoming city won't disappoint. PNC Park and Monongahela Incline are just a couple of the must-sees in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.


Activities and attractions in Oakland

Are you hoping to find top things to see and do in the city? Venture out of your cozy vacation rental and check out everything that Oakland has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • National Aviary (2.7 mi / 4.4 km)
  • Frick Park (3.2 mi / 5.2 km)
  • Pittsburgh Zoo and PPG Aquarium (3.4 mi / 5.5 km)
  • Sandcastle Water Park (3.6 mi / 5.8 km)
  • Kennywood (6.2 mi / 10 km)
  • South Park Golf Course (8.4 mi / 13.6 km)
Natural features

Exploring the natural features in Oakland

Whether you're an adventurous traveler or just want to appreciate the scenery, Oakland is a great place to spend some time outside. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Schenley Park (0.6 mi / 1 km)
  • Phipps Conservatory (0.6 mi / 1 km)
  • Mellon Park (2.3 mi / 3.8 km)
  • Point State Park (2.5 mi / 4 km)
  • Frick Park (3.2 mi / 5.2 km)
  • West End-Elliott Overlook Park (4 mi / 6.4 km)
How to get there

Transportation to and around Oakland

The nearest airport is in Pittsburgh, PA (PIT-Pittsburgh Intl.), located 16 mi (25.7 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Latrobe, PA (LBE-Arnold Palmer Regional), which is 31.5 mi (50.6 km) away.

How many vacation rentals are available around Oakland, Pittsburgh?

Our 2020 property listings offer a large selection of 27 vacation rentals around Oakland. From 16 house rentals to 9 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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:

  • Downtown: 86 vacation rentals
  • South Side Flats: 80 vacation rentals
  • Shadyside: 22 vacation rentals
  • Lawrenceville: 29 vacation rentals
  • East Allegheny: 27 vacation rentals

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

What are the popular point of interests near where I can stay when traveling to Oakland?

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

  • University of Pittsburgh: 304 vacation rentals
  • University of Pittsburgh Medical Center: 303 vacation rentals
  • The Nationality Rooms: 304 vacation rentals
  • Pittsburgh Zoo and PPG Aquarium: 305 vacation rentals
  • USS Requin: 301 vacation rentals

But there are many other points of interest around Oakland listed on Vrbo 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. Vrbo has 16 Houses in Oakland. Our other popular types of vacation rentals in Oakland include:

  • Condos/Apartments: 9 rentals available
  • Studios: 8 rentals available
  • Townhouses: 2 rentals available

Can I find a vacation rental with pool in Oakland?

Yes, you can select your preferred vacation rental with pool among our 2 vacation rentals with pool available in Oakland. Please use our search bar to access the selection of vacation rentals available.

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