South Oakland vacation rentals

We found 115 vacation rentals — enter your dates for availability

Welcome to the vibrant heart of South Oakland, where urban parks like Leland Heights provide a serene backdrop for relaxation amidst the lively streets filled with friendly locals and cultural treasures. Explore fascinating attractions, from the Carnegie Museum of Natural History to the enchanting Phipps Conservatory, perfect for family adventures. With diverse accommodations ranging from cozy houses to stylish apartments, your group will relish the comfort and convenience of a vacation rental, creating a home-like experience that enhances your unforgettable getaway.

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Find out more about South Oakland

Why visit South Oakland

  • Urban Parks: Enjoy the beautiful scenery and outdoor relaxation at local parks like Leland Heights.
  • Local Attractions: Discover the vibrant Oakland neighborhood with its friendly locals and city-themed attractions.
  • Recreational Activities: Have fun at the local skating rink, perfect for families and outdoor enthusiasts.
  • Diverse Accommodations: Choose from cozy vacation homes, stylish apartments, and charming cottages to suit your needs.
  • Cultural Experience: Immerse yourself in the rich culture offered by medical centers and arts venues in the area.

Popular types of accommodation around South Oakland

If you're planning a getaway to South Oakland, you're in for a treat. Our vacation rentals offer a variety of accommodations to suit your needs. From cozy houses to stylish apartments and charming cottages, there's something for everyone. Whether you're searching for Oakland Pittsburgh apartments or specific options in South Oakland, we’re here to help you find the perfect place to stay and enjoy your trip.

  • Houses: Ideal for families or groups, these spacious homes offer a comfortable and private retreat in South Oakland.
  • Apartments: Perfect for couples or solo travelers, these fully-equipped spaces provide convenience and easy access to local attractions.
  • Cottages: Quaint and cozy, these charming accommodations are perfect for a peaceful getaway amidst nature.
  • Condos: Offering modern amenities and often located in vibrant areas, condos are great for those seeking a blend of comfort and style.
  • Cabins: Rustic and inviting, cabins provide a unique experience for those looking to immerse themselves in the natural surroundings.**

Top attractions near South Oakland

South Oakland, Pittsburgh, offers a vibrant mix of city-themed attractions perfect for family and outdoor vacations. Visitors can explore local points of interest like medical centers, urban parks, and arts centers, providing a rich cultural experience. Whether you're interested in the neighborhood ambiance, seeking rental options, or requesting tours, South Oakland has something for everyone, making it an ideal destination for travelers looking to immerse themselves in the local scene.

  • University of Pittsburgh Medical Center: A prominent healthcare facility known for its innovative medical services and research. Visitors can appreciate the blend of modern architecture and community-focused atmosphere, making it a unique experience in the realm of healthcare.
  • Carnegie Museum of Natural History: This museum offers an enriching experience with its extensive fossil collections and diverse exhibits. Families can explore the wonders of our planet's history while enjoying interactive displays and captivating artifacts.
  • Phipps Conservatory: A beautiful conservatory featuring stunning gardens and exotic plants. It provides a serene outdoor escape, perfect for families to enjoy nature's beauty while learning about sustainable practices and plant diversity.

Things to do recommended for couples

Ready for a romantic getaway in South Oakland? Visit the Oakmont Country Club, just 9 miles away, where luxury vibes set the perfect backdrop for a special date. Enjoy the beautiful surroundings and unwind together in this exclusive setting.

Things to do recommended for families

Your family will love exploring the interactive exhibits at the Carnegie Museum of Natural History, just a short drive away. Enjoy a picnic at Schenley Park, where kids can play and the whole family can unwind in nature.

Things to do recommended for groups

Explore the vibrant local art scene by visiting the nearby Andy Warhol Museum or enjoy a group picnic at Schenley Park. For a unique experience, consider a guided brewery tour to taste local craft beers and learn about Pittsburgh's brewing history.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When traveling with a group, with family, bringing your pets, or seeking extended stays, it's important to prioritize your preferences in your search. Here are some helpful Vrbo booking tips for you.

  • Traveling to South Oakland with a group: Think about how many bedrooms you'll require, as well as amenities like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to South Oakland with young kids: Traveling with young kids can be difficult. It's important to prioritize their comfort and safety, along with amenities that are suitable for their age, like a private swimming 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 trip isn’t truly enjoyable without their furry companion by their side. If you can relate, explore Vrbo properties that welcome pets. Many 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 that offer special rates 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 rentals. Don't forget to include features like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near South Oakland

South Oakland, Pittsburgh, offers a vibrant mix of urban charm and family-friendly attractions. Explore the lively Oakland neighborhood, where friendly locals welcome you to enjoy beautiful scenery along Parkview Avenue. Don't miss the fun at the local skating rink and the serene Leland Heights for outdoor relaxation. This area is perfect for those seeking a delightful blend of city life and nature, making it an ideal destination for your vacation.

  • Pittsburgh: Nestled in southwestern Pennsylvania, Pittsburgh is a vibrant city known for its rich industrial history and cultural diversity. South Oakland, where you’ll be based, is a lively neighborhood that serves as a gateway to a multitude of attractions. Visitors can enjoy family-friendly activities, explore urban parks, or catch thrilling sports events at local stadiums. The city is home to renowned educational institutions and shopping centers that add to its dynamic atmosphere. With its unique blend of modernity and tradition, Pittsburgh offers a memorable urban experience.
  • Downtown Pittsburgh: Located a mere 2 miles from South Oakland, Downtown Pittsburgh is the bustling heart of the city. This neighborhood is perfect for families and those seeking a city-themed adventure. Here, you can visit impressive arenas for live entertainment, explore educational venues, or shop at popular retail centers. The proximity to landmarks like sports stadiums and urban parks makes Downtown a convenient and entertaining destination. Whether you're enjoying the scenic views along the rivers or indulging in local cuisine, Downtown Pittsburgh promises an exciting urban experience.
  • Central Oakland: Just 0.5 miles from South Oakland, Central Oakland is a culturally rich neighborhood that offers a delightful mix of city life and historic charm. Ideal for families and culture enthusiasts, Central Oakland features renowned educational institutions and historic buildings that reflect the area’s rich heritage. Enjoy the vibrant atmosphere as you explore local attractions, including sports stadiums and modern college campuses. With its array of entertainment options and cultural landmarks, Central Oakland is a must-visit for anyone looking to immerse themselves in the local scene.

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 in June to July and October, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 LowSlightly Low
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 SunnySlightly HighSlightly 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 SunnyAverageAverage
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 CloudyAverageAverage

Booking with Vrbo is simple

Are you eager to save on your upcoming journey? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, booking an extended stay can lead to noteworthy savings. To discover a Vrbo property that aligns with your budget, make use of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect option for your needs.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, and manage your travel arrangements. You can easily access properties you've saved and booked under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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 rental, with around 30 available throughout the area. These properties typically offer spacious living environments, often featuring multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation, making them ideal for families or groups. Additionally, there are approximately 13 apartments for those looking for a more compact accommodation option. These apartments usually include essential amenities such as kitchen facilities and comfortable living spaces.
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 rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals and enjoy a home-like experience. Many rentals also feature a designated workspace with a desk, suiting those who may need to work or study during their stay. Onsite parking is commonly available, making it convenient for guests with vehicles. Additionally, properties often provide a coffee and tea maker for a quick caffeine fix, and many have decks or patios where guests can relax and enjoy the outdoors.
Can I find family house rentals in South Oakland?
In South Oakland, Pennsylvania, there are numerous family-friendly house rentals available—around 27 in total. This vibrant neighborhood offers a mix of spacious homes great for families looking to explore the area. Many of these properties come equipped with full kitchens, allowing for convenient meal preparation, and comfortable living spaces where everyone can gather after a day of activities.Visitors will appreciate amenities such as outdoor areas for kids to play, Wi-Fi for staying connected, and ample bedrooms to accommodate larger groups. The locale is close to several points of interest, including parks, local shops, and cultural attractions, making it an ideal base for those wanting to experience the charm of the neighborhood.
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 hot tubs, superb for relaxation after a day of exploring the area. The neighborhood is conveniently located near the University of Pittsburgh and offers a mix of residential charm and easy access to local amenities. Travelers can expect properties that provide comfortable living spaces, fully equipped kitchens, and outdoor areas where guests can unwind. Some rentals may also include private hot tubs, which add a touch of luxury to the 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.
Can I book pet-friendly vacation rentals in South Oakland?
In South Oakland, travelers can find a variety of pet-friendly vacation rentals available, with approximately 17 options to choose from. These rentals typically offer amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. Many properties are designed to accommodate families or groups, making them suitable for a comfortable stay.The neighborhood itself is known for its proximity to parks and green spaces, allowing for enjoyable walks and outdoor activities with pets. Nearby parks provide trails and open areas superb for exercising pets and enjoying nature.
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?
The best time to visit South Oakland for a vacation rental is during the peak season from July to September. This vibrant period attracts travelers eager to explore the area's rich cultural scene, outdoor activities, and local events. With warm summer temperatures typically ranging from the mid-70s to mid-80s Fahrenheit, it's an ideal time for sightseeing, enjoying local parks, and immersing yourself in community festivities.July stands out as the most popular month, when the atmosphere is lively, and you can experience an array of outdoor concerts, festivals, and local attractions. Whether you're strolling through neighborhood parks or visiting nearby attractions, the summer months offer a variety of activities that cater to adventure seekers and those looking to relax in a lively environment.For those seeking a more budget-friendly option, December presents a charming alternative. While this month is quieter and falls outside the main tourist season, it offers unique holiday events and a cozy atmosphere great for enjoying the local culture. Visiting during this time provides the chance to experience South Oakland in a different light, with fewer crowds and a more intimate feel.Ultimately, your choice of when to visit South Oakland will depend on whether you prefer the bustling energy of summer or the serene charm of winter festivities.
Are there any remote work vacation rentals in South Oakland?
In South Oakland, Pennsylvania, there are numerous options for remote work vacation rentals, with around 40 available in the area. Travelers can expect properties equipped with essential amenities for a productive work-from-home experience, such as high-speed internet, dedicated desk spaces, and sometimes even office setups with printers available for use. Many of these rentals also feature comfortable living areas that allow for relaxation after a day of work.The neighborhood is conveniently located near the University of Pittsburgh and Carnegie Mellon University, making it an ideal spot for those looking to combine work and leisure, with easy access to local cafes and parks for breaks. Additionally, the area's vibrant community offers a mix of dining and entertainment options, ensuring that remote workers can enjoy a fulfilling stay while meeting their professional needs. 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, Pennsylvania, United States of America?
In South Oakland, Pennsylvania, visitors can explore a variety of attractions that highlight the area's vibrant community and proximity to larger urban experiences. The neighborhood is situated near the University of Pittsburgh, making it a hub for cultural and educational activities. The Cathedral of Learning, a striking landmark on campus, offers free tours that showcase its stunning architecture and multicultural classrooms.Additionally, the nearby Schenley Park provides a beautiful green space for outdoor activities, including walking trails, picnic areas, and a golf course. The park is also home to the Phipps Conservatory and Botanical Gardens, where guests can enjoy diverse plant collections and seasonal floral displays.For those interested in arts and culture, the Andy Warhol Museum is located just a short drive away in the North Shore area, offering insight into the life and work of the iconic artist. The local dining scene features a mix of casual eateries and more upscale options, suiting a variety of tastes and preferences.
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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