South Oakland holiday rentals
We found 113 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.
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Find the best place to stay - South Oakland

City Skyline - Outside decks - Contemporary
Sleeps 10 · 4 bedrooms · 3+ bathrooms

Easy University & Hospital Access! Pittsburgh Home
Sleeps 6 · 3 bedrooms · 1 bathroom

Stylish 3-bedroom Oakland apartment near universities, hospitals, and downtown.
Sleeps 6 · 3 bedrooms · 1 bathroom

Chic City Apartment
Sleeps 4 · 1 bedroom · 1 bathroom

Spacious Home with Porch Sleeps 6 Near Pitt & UPMC
Sleeps 6 · 2 bedrooms · 3 bathrooms

By PITT and Presbyterian| Outdoor Living| Free Pkg
Sleeps 8 · 4 bedrooms · 3+ bathrooms
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental in South Oakland?
In South Oakland, holiday houses are the most popular type of holiday rental, with around 120 available in the area. These properties are typically spacious and well-equipped, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many of these homes also include outdoor spaces, such as gardens or patios, where guests can relax after a day of exploring. Additionally, there are about 52 apartments and several condos available, offering a more compact option for those looking for a convenient base close to local amenities.
What are popular rental amenities in South Oakland?
In South Oakland, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and desks that provide a suitable workspace for those needing to catch up on tasks during their stay. Onsite parking is also a common feature, making it convenient for travellers with vehicles. Additionally, many rentals come with coffee and tea makers for a warm beverage at any time, and outdoor spaces such as decks or patios where guests can relax and enjoy the fresh air.
Can I find family house rentals in South Oakland?
In South Oakland, Pennsylvania, there are numerous family-friendly house rentals available, with around 27 options to choose from. This vibrant neighbourhood is in close proximity to several parks and recreational areas, making it an excellent choice for families. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.Visitors will likely appreciate amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay. Additionally, South Oakland's location provides easy access to attractions like the nearby Carnegie Mellon University and the bustling cultural scene in Pittsburgh.
Can I book pet-friendly holiday rentals in South Oakland?
Yes, in South Oakland, there are several pet-friendly holiday rentals available, with a total of 17 options to choose from. Many of these properties come equipped with various amenities that cater to both humans and pets, such as spacious yards, pet-friendly furnishings, and easy access to local parks and green spaces.The neighbourhood itself is well-suited for pet owners, with close proximity to parks where you can take your furry friends for walks or play. Additionally, South Oakland's charming residential streets provide a pleasant environment for exploring with pets.
When is the best time to visit South Oakland for a holiday rental?
The best time to book a holiday rental in South Oakland is during the peak season from July to September. This vibrant period draws visitors eager to enjoy the warm weather and engage in various outdoor activities. With temperatures typically ranging from the mid-teens to low 30s Celsius, it's ideal for exploring the local parks, enjoying picnics, or simply soaking up the sun at nearby attractions.July stands out as the most popular month, when the community comes alive with events and activities that appeal to families and adventure-seekers alike. You'll find everything from farmers' markets to outdoor concerts, creating a lively option that enhances your holiday experience.For those looking for a more budget-friendly option, consider visiting in December. During this time, this month offers a unique charm with holiday decorations and a chance to experience the area's local culture in a more relaxed setting.Ultimately, your choice will depend on whether you prefer the bustling energy of summer adventures or the peaceful charm of winter festivities.
Are there any remote work holiday rentals in South Oakland?
In South Oakland, Pennsylvania, there are numerous remote work holiday rentals available, with around 160 options to choose from. This vibrant neighbourhood, located near the University of Pittsburgh, offers a variety of amenities suiting remote workers. Many of these rentals include dedicated office spaces or desks, ensuring a productive environment. High-speed Wi-Fi is commonly provided, allowing for seamless connectivity during work hours.Additionally, travellers can expect comfortable living areas and kitchen facilities, ideal for those who may wish to prepare their own meals. Proximity to local cafes and restaurants adds convenience for breaks or a change of scenery while working. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
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 reflect the area's vibrant culture and proximity to great sites. The neighbourhood is adjacent to the University of Pittsburgh, where the Carnegie Museum of Natural History and the Carnegie Museum of Art are located, offering enriching experiences for art and science enthusiasts alike. The nearby Phipps Conservatory and Botanical Gardens in Schenley Park provide a beautiful setting for those who appreciate nature and horticulture.For sports fans, the area is close to the home of the Pittsburgh Panthers, and a short journey will take you to Heinz Field and PNC Park, where you can catch a football or baseball game. Additionally, South Oakland is well-connected to the cultural offerings of downtown Pittsburgh, making it easy to access attractions such as the Andy Warhol Museum and the historic Strip District. The neighbourhood itself features local cafes and shops, contributing to its community charm.
Are all fees included in the South Oakland holiday homes prices shown on Stayz?
Stayz 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.
Are there any South Oakland holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 any discounts for South Oakland holiday homes?
You can find great discounts on holiday homes in South Oakland on Stayz, 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.
Can I change or cancel my South Oakland holiday home booking on Stayz?
To find South Oakland holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in South Oakland?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a South Oakland holiday home?
Book your South Oakland holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in South Oakland?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in South Oakland to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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