South Oakland vacation rentals

We found 104 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in South Oakland to find one that's perfect for your trip. Whether you're traveling with your kids or with friends, vacation rentals have the amenities you expect for your stay, which might include parking and a washer and dryer. No matter what you're looking for, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

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Find out more about South Oakland

Why visit South Oakland

  1. Educational institutions: Explore the vibrant campuses of modern colleges and universities that enrich the area.
  2. Outdoor activities: Enjoy urban parks and outdoor adventures suitable for families and outdoor enthusiasts.
  3. Cultural experiences: Engage in artistic excursions and discover local attractions that reflect the community's charm.
  4. Walkable neighborhoods: Stroll through friendly streets filled with shops, dining options, and local art.
  5. Cozy accommodations: Choose from a variety of comfortable lodging options, including apartments and vacation homes.

Popular types of accommodation around South Oakland

If you're exploring vacation rentals in South Oakland, you're in for a treat! Our most popular accommodations include cozy apartments, convenient apart-hotels, and charming houses. Whether you're searching for apartments in Oakland, Pittsburgh, or specifically South Oakland, we offer a range of options to suit your needs. Enjoy transparency, savings, and the reassurance of finding the perfect place to stay during your visit!

  • Apartments: The top choice for travelers in South Oakland, offering convenient amenities and a home-like atmosphere.
  • Houses: A popular option for families and groups, providing spacious accommodations and a personal touch.
  • Condos: Ideal for those seeking a blend of comfort and modern living, often located in vibrant neighborhoods.
  • Cottages: A charming getaway option, perfect for a cozy and intimate vacation experience.
  • Chalets: A unique lodging choice, offering a distinctive style and an inviting ambiance for relaxation.**

Top attractions around South Oakland

South Oakland, Pittsburgh, is an ideal destination for city, family, and outdoor vacations. Visitors can explore a variety of attractions, including modern colleges and universities, entertainment arenas, and urban parks. This vibrant area offers cultural experiences and activities that cater to families and outdoor enthusiasts alike, ensuring a memorable getaway for all travelers.

  1. University of Pittsburgh: A prestigious institution known for its stunning Gothic architecture and vibrant campus life, offering a unique blend of academic excellence and city energy, just 1 mile away from South Oakland.
  2. PPG Paints Arena: Home to thrilling sports events and concerts, this family-friendly venue provides an electrifying atmosphere for entertainment, located 2 miles from South Oakland.
  3. PNC Park: Renowned for its picturesque views of the Pittsburgh skyline, this urban park is perfect for family outings, outdoor activities, and enjoying the city's vibrant atmosphere, situated 3 miles away from South Oakland.

Things to do recommended for couples

For a romantic getaway in South Oakland, take a scenic ride on the Monongahela Incline for stunning views, catch a live show at the Rex Theater for an entertaining evening, and indulge in luxury at the Oakmont Country Club for a perfect couple's retreat.

Things to do recommended for families

Your family will love the excitement at Acrisure Stadium, just 3 miles away, and the serene beauty of Schenley Park, only 0.6 miles from South Oakland. For a splashing good time, head to Sandcastle Water Park, also 3 miles away, for thrilling water adventures.

Things to do recommended for groups

Experience the excitement at Rivers Casino, just 4 miles away, for a thrilling night out. Enjoy shopping and dining at Station Square, 3 miles from South Oakland, perfect for families. Don’t miss the cultural performances at Byham Theater, also 3 miles away, offering entertainment for all ages.

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

When planning your trip—whether you're traveling with a group, family, bringing pets, or seeking extended stays—it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to South Oakland with a group: Think about how many bedrooms you require, as well as any amenities that might be important, like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to South Oakland with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to South Oakland: For many families, a vacation wouldn't be the same without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting South Oakland: If you're seeking vacation rentals with special offers 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 parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around South Oakland

South Oakland, Pittsburgh offers a vibrant blend of family-friendly activities and outdoor adventures. Explore the walkable neighborhoods filled with friendly faces and artistic excursions. Discover the charm of the South Side of Oakland, where local attractions and dining options abound. Whether you're strolling through the streets or enjoying the nearby parks, South Oakland promises a memorable experience for every traveler.

  • Downtown Pittsburgh: Nestled about 3 miles from South Oakland, Downtown Pittsburgh is the vibrant core of the city, where visitors can immerse themselves in a rich tapestry of family-friendly activities and urban excitement. This area is renowned for its arena entertainment facilities, bustling shopping malls, and a variety of educational institutions. Notable landmarks include the iconic sports stadiums and lush urban parks, perfect for a leisurely stroll or a family picnic. Whether you're catching a game or enjoying a concert, Downtown Pittsburgh offers a dynamic travel experience that caters to all ages.
  • Oakland: Just 0.9 miles from South Oakland, Oakland is a cultural hub that attracts travelers seeking a blend of city life, family fun, and artistic flair. This neighborhood is home to several prominent educational institutions and arena entertainment venues. Visitors can explore the modern college campuses, engage with the vibrant arts scene, or enjoy the local stadium events. With its rich cultural offerings and lively atmosphere, Oakland is an ideal spot for families and culture enthusiasts alike.
  • Central Oakland: Located a mere 0.5 miles from South Oakland, Central Oakland is a bustling neighborhood known for its accessibility to educational facilities and recreational areas. It offers a mix of cultural experiences and family-friendly activities, making it a great destination for all visitors. The area is characterized by modern college universities and sports facilities, which host a variety of events throughout the year. Whether you're looking to enjoy a local game or simply soak in the lively atmosphere, Central Oakland provides a welcoming experience for tourists and locals alike.

Best time to go to South Oakland

If you're planning a trip to South Oakland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like December to February 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 CloudySlightly LowSlightly Low
February31.3°F (-0.4°C)Light RainMostly CloudySlightly LowSlightly Low
March40.5°F (4.7°C)Light RainMostly CloudySlightly LowAverage
April51.1°F (10.6°C)Light RainMostly CloudyAverageAverage
May61.7°F (16.5°C)Light RainMostly SunnyAverageSlightly High
June69.4°F (20.8°C)Light RainMostly SunnyAverageSlightly High
July73.9°F (23.3°C)Light RainMostly SunnyAverageAverage
August72.1°F (22.3°C)Light RainMostly SunnySlightly HighAverage
September66.2°F (19.0°C)Light RainMostly SunnySlightly HighAverage
October54.7°F (12.6°C)Light RainMostly SunnySlightly HighSlightly High
November42.6°F (5.9°C)Light RainMostly SunnyAverageAverage
December35.2°F (1.8°C)Light RainMostly CloudyAverageSlightly Low

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, booking an extended stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, use our helpful filters to search by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash™ on the full booking amount. Being the organizer truly has its rewards! Enroll in our One Key rewards program to unlock exclusive savings for members and earn OneKeyCash™ on eligible stays. Sign up today to start reaping the benefits!

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new trips, keep track of your ongoing plans, and manage your bookings. Your saved or booked properties are thoughtfully categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Frequently asked questions

What is the most popular type of vacation rental in South Oakland?
In South Oakland, vacation houses are the most popular type of vacation rental, with around 40 available throughout the area. These properties are often situated in residential neighborhoods, providing a spacious and comfortable environment for families or groups. Most vacation houses come equipped with multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or backyards, great for relaxing after a day of exploring. Additionally, there are approximately 17 apartments in the area, which offer a more compact living option, typically featuring cozy living areas and kitchenettes. Cottages are also available, though in smaller numbers, contributing to the diverse range of rental options in South Oakland.
Are there any beach house rentals in South Oakland?
In South Oakland, Pennsylvania, there are several beach house rentals available. These properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and comfortable living areas. While the area itself is not directly on the beach, these rentals provide a cozy home base for exploring nearby attractions. Guests can expect amenities like outdoor seating areas, which are superb for relaxing after a day of local adventures.
How much does it cost to rent a vacation home in South Oakland?
Prices for vacation rentals in South Oakland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in South Oakland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for South Oakland vacation house rentals?
You can find great discounts on house rentals in South Oakland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in South Oakland?
In South Oakland, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals conveniently. Many rentals also feature coffee and tea makers for a warm beverage at any time of day. Outdoor spaces like patios and decks provide great spots for relaxation or socializing. Additionally, onsite parking is a common amenity, making it easy for guests to explore the area without worrying about finding a place to park.
Are there any family house rentals in South Oakland?
In South Oakland, Pennsylvania, there are numerous family-friendly house rentals available, with around 34 options to choose from. This vibrant neighborhood offers a great mix of spacious homes that cater to families, featuring amenities such as large living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and enjoy the fresh air.

Visitors will appreciate the proximity to points of interest like the University of Pittsburgh and the Carnegie Mellon University campus, both of which offer cultural and recreational activities. Additionally, the nearby Schenley Park provides ample opportunities for outdoor adventures, including hiking trails, playgrounds, and picnic areas, making it an excellent spot for family outings.
Can I rent a vacation home with a pool or hot tub in South Oakland?
In South Oakland, Pennsylvania, there are several vacation homes available for rent that feature pools and hot tubs. This neighborhood, known for its vibrant community and proximity to the University of Pittsburgh, offers a mix of residential charm and accessibility to local amenities. Travelers can expect properties with inviting outdoor spaces, including private pools and relaxing hot tubs, great for unwinding after a day of exploring the area. Many rentals also come equipped with modern kitchens, spacious living areas, and outdoor patios or decks, enhancing the overall comfort of your stay.
Are there any South Oakland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in South Oakland with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there pet-friendly vacation rentals in South Oakland?
Yes, there are numerous pet-friendly vacation rentals available in South Oakland, Pennsylvania. This neighborhood offers a variety of accommodations that cater to travelers with pets, providing a welcoming environment for your furry friends. Expect to find rentals equipped with amenities such as fully stocked kitchens, outdoor spaces, and comfortable living areas.

South Oakland is conveniently located near several parks, making it easy to enjoy outdoor activities with your pets. Nearby Schenley Park features trails, open spaces, and beautiful landscapes, great for walking or playing with your dog. Additionally, the area includes pet-friendly cafes and shops, adding to the overall experience for travelers who wish to explore the neighborhood with their pets.
Can I find long-stay vacation rentals in South Oakland?
A long-stay vacation rental in South Oakland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit South Oakland for a vacation rental?
July marks the peak season for those looking to experience the vibrant charm of South Oakland, Pennsylvania. This summer month is particularly appealing for travelers who enjoy outdoor activities, as the warm weather invites exploration of local parks and recreational areas. The area comes alive with visitors eager to participate in community events and enjoy the lively atmosphere.

The months of July through September offer a range of tourist activities, including festivals and outdoor concerts, making it an ideal time for those who thrive on socializing and cultural experiences. Expect comfortable temperatures, typically ranging from the mid-70s to low 80s Fahrenheit, great for sightseeing or enjoying a leisurely stroll through the neighborhood.

If you're looking for a more budget-friendly option, consider planning your visit in December. This month provides a unique opportunity to experience the charming holiday decorations around the area, along with quieter streets and the chance to enjoy the local culture without the bustle of peak tourist crowds.

Ultimately, the best time to book a vacation rental in South Oakland depends on your preferences.
Are there any remote work vacation rentals in South Oakland?
In South Oakland, Pennsylvania, there is a solid selection of vacation rentals suitable for remote work, with around 52 options available. Travelers can expect well-equipped accommodations that cater specifically to those working remotely. Many properties feature dedicated office spaces, desks, and ergonomic chairs to ensure a comfortable working environment. Amenities such as high-speed Wi-Fi, laptop workspaces, and even computer monitors are commonly included, making it easy to stay productive while enjoying a change of scenery.

This neighborhood is conveniently located near the University of Pittsburgh and Carnegie Mellon University, providing access to vibrant local cafes and restaurants great for breaks or informal meetings. Additionally, outdoor spaces and parks nearby offer opportunities for relaxation after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a South Oakland vacation rental?
Book your South Oakland vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in South Oakland?
In South Oakland, Pennsylvania, visitors can explore several attractions that highlight the area's charm and accessibility. The neighborhood is close to the University of Pittsburgh, where travelers can enjoy the beautiful campus and visit the Carnegie Museum of Natural History and the Carnegie Museum of Art, both located nearby in Oakland. The Phipps Conservatory and Botanical Gardens, also in the vicinity, offers stunning floral displays and is a great spot for nature enthusiasts.

For those interested in sports, the area is just a short distance from Heinz Field and PNC Park, where guests can catch a Pittsburgh Steelers or Pirates game. The neighborhood is well-served by public transportation, making it easy to access these attractions and explore the wider Pittsburgh area.
Can I change or cancel my South Oakland home rental booking on Vrbo?
To find South Oakland vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the South Oakland vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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