Photo by Jessie Lewis

South Oakland holiday lettings

We found 106 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in South Oakland to find one that's perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - South Oakland

Showing deals for:27 Feb - 6 Mar

Image gallery for Extravagant Duplex 6BR-4BR! Garage/Sleeps 16!

Living area
9.0 out of 10, Wonderful, (9 reviews)
Wonderful
(9 reviews)

Extravagant Duplex 6BR-4BR! Garage/Sleeps 16!

Pittsburgh, PA

7% off
Price is £2,932
for 7 nights, 1 home
£419 per night
includes taxes & fees
Extravagant Duplex 6BR-4BR! Garage/Sleeps 16!

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Frequently asked questions

What is the most popular type of holiday rental in South Oakland?
In South Oakland, holiday houses are the most popular rental choice, with around 40 available in the area. These properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Additionally, many of these houses come with outdoor spaces, such as gardens or patios, allowing guests to enjoy the fresh air and relax after a day of exploring. There are also approximately 17 apartments in South Oakland, which provide a more compact option for travellers, often including modern amenities and convenient access to local shops and dining.
How much does it cost to rent a holiday home in South Oakland?
Prices for holiday 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 holiday 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, allowing guests to prepare their own meals and enjoy a home-cooked experience. Many properties also feature coffee and tea makers, enabling travellers to enjoy a warm beverage at their convenience. Outdoor spaces such as patios or decks are commonly available, providing a pleasant area to relax and unwind after a day of exploring. Additionally, onsite parking is a sought-after amenity, making it easier for visitors travelling by car to find convenient accommodation.
Are there any family house rentals in South Oakland?
In South Oakland, Pennsylvania, there are numerous family-friendly house rentals available, with around 32 options to choose from. This vibrant neighbourhood is conveniently located near the University of Pittsburgh, making it an ideal base for families visiting students or exploring the area. Many of these homes offer spacious living rooms, well-equipped kitchens for preparing family meals, and outdoor spaces where children can play or families can relax together.
Can I rent a holiday home with a pool or hot tub in South Oakland?
In South Oakland, Pennsylvania, there are several holiday homes available for rent that feature pools or hot tubs. This neighbourhood, known for its proximity to the University of Pittsburgh and vibrant community atmosphere, offers a variety of rental options. Many properties come equipped with amenities such as private hot tubs, outdoor seating areas, and well-appointed kitchens, making them ideal for relaxing after a day of exploring the local area.
Are there any South Oakland holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in South Oakland with parking available—perfect for families or travellers 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 holiday rentals in South Oakland?
In South Oakland, there are several pet-friendly holiday rentals available for those looking to enjoy the area with their furry companions. Many of these accommodations are equipped with essential amenities such as fully furnished kitchens, comfortable living spaces, and outdoor areas where pets can play.
Can I find long-stay holiday rentals in South Oakland?
A long-stay holiday rental in South Oakland is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit South Oakland for a holiday rental?
The best time to visit South Oakland for a holiday rental is during the vibrant summer months, particularly from July to September. This peak season draws a lot of visitors eager to enjoy the lively atmosphere and countless outdoor activities available in the area. With warm temperatures averaging around 25°C, it's an ideal time for families and friends to explore local parks, attend community events, and immerse themselves in the cultural offerings of South Oakland.

July stands out as the most popular month, where you can experience the bustling energy of the community. During this time, the area comes alive with festivals, concerts, and various recreational activities that cater to all ages. The proximity to Pittsburgh also allows for easy day trips, ensuring that there's always something to see and do.

If you're looking for a more budget-friendly experience, consider planning your visit in December. This month offers a unique charm with festive decorations and a quieter atmosphere, superb for enjoying a cozy retreat. Although it's cooler, with temperatures dipping to around 3°C, visitors can still appreciate the local holiday spirit and explore indoor attractions.
Are there any remote work holiday rentals in South Oakland?
In South Oakland, Pennsylvania, there are numerous remote work holiday rentals available, with around 52 properties to choose from. This vibrant neighbourhood offers a variety of accommodations suitable for those looking to work remotely while enjoying the comforts of home. Many of these rentals are equipped with essential amenities for remote work, including Wi-Fi, dedicated desk spaces, and comfortable office chairs, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a South Oakland holiday rental?
Book your South Oakland holiday 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 holiday 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 reflect the area's vibrant community and its proximity to the University of Pittsburgh. The beautiful Schenley Park is nearby, offering expansive green spaces, walking trails, and recreational facilities, making it a superb spot for outdoor activities. The park also houses the Phipps Conservatory and Botanical Gardens, which features stunning floral displays and educational exhibits.
Can I change or cancel my South Oakland home rental booking on Vrbo?
To find South Oakland holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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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