
Photo by Jessie Lewis
South Oakland holiday lettings
We found 105 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:1 Aug - 8 Aug
Image gallery for Charming Home • Vibrant Neighborhood

1010 out of 10 rating
Exceptional
(11 reviews)
Charming Home • Vibrant Neighborhood
Pittsburgh, PA
16% off
Price is £1,750
£1,750
£250 per night
includes taxes & fees
Image gallery for Amazingly Homey w/Garage + Outdoor Space! 5B/2B

9.49.4 out of 10 rating
Exceptional
(15 reviews)
Amazingly Homey w/Garage + Outdoor Space! 5B/2B
Pittsburgh, PA
7% off
Price is £2,839
£2,839
£406 per night
includes taxes & fees
Image gallery for Elegant & Cozy Escape - 5Beds/2.5Bath - Sleeps 10

1010 out of 10 rating
Exceptional
(21 reviews)
Elegant & Cozy Escape - 5Beds/2.5Bath - Sleeps 10
Pittsburgh, PA
7% off
Price is £2,519
£2,519
£360 per night
includes taxes & fees
Image gallery for Gorgeous Southside Slopes home with outdoor hot tub and city view!

9.89.8 out of 10 rating
Exceptional
(50 reviews)
Gorgeous Southside Slopes home with outdoor hot tub and city view!
Pittsburgh, PA
7% off
Price is £2,732
£2,732
£390 per night
includes taxes & fees
Image gallery for Historic Home • Former Convent

1010 out of 10 rating
Exceptional
(20 reviews)
Historic Home • Former Convent
Pittsburgh, PA
16% off
Price is £4,898
£4,898
£700 per night
includes taxes & fees
Image gallery for Historic Home In The South Side

1010 out of 10 rating
Exceptional
(30 reviews)
Historic Home In The South Side
Pittsburgh, PA
12% off
Price is £1,080
£1,080
£154 per night
includes taxes & fees
Image gallery for King Bed / Free Parking / Arcade / Fire Pit

1010 out of 10 rating
Exceptional
(8 reviews)
King Bed / Free Parking / Arcade / Fire Pit
Pittsburgh, PA
7% off
Price is £1,628
£1,628
£233 per night
includes taxes & fees
Image gallery for Stunning City View! Sleeps 10. Kids Game Room and Large Rooftop.

9.89.8 out of 10 rating
Exceptional
(8 reviews)
Stunning City View! Sleeps 10. Kids Game Room and Large Rooftop.
Pittsburgh, PA
7% off
Price is £1,720
£1,720
£246 per night
includes taxes & fees
Image gallery for Cozy Southside Pitt home w/ Pool Table +Yard

1010 out of 10 rating
Exceptional
(7 reviews)
Cozy Southside Pitt home w/ Pool Table +Yard
Pittsburgh, PA
7% off
Price is £1,607
£1,607
£230 per night
includes taxes & fees
Image gallery for Large 1BR on hill close to everything in Pitt

9.29.2 out of 10 rating
Wonderful
(10 reviews)
Large 1BR on hill close to everything in Pitt
Pittsburgh, PA
13% off
Price is £877
£877
£125 per night
includes taxes & fees
Image gallery for Carey Way Quarters – Modern 2BR Near Carson Street

9.09.0 out of 10 rating
Wonderful
(7 reviews)
Carey Way Quarters – Modern 2BR Near Carson Street
Pittsburgh, Pennsylvania
8% off
Price is £1,065
£1,065
£152 per night
includes taxes & fees
Image gallery for House on a hill - view of Pittsburgh

9.69.6 out of 10 rating
Exceptional
(22 reviews)
House on a hill - view of Pittsburgh
Pittsburgh, Pennsylvania
13% off
Price is £1,333
£1,333
£190 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - South Oakland
#27 Tiny Apt near PITT uni/CMU/UPMC Presbyterian
Sleeps 4 · 2 bedrooms · 1 bathroom
⁂ Cozy Nook off Carson - Free Parking & Private Entry ⁂
Sleeps 3 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
❤️Cozy Townhome on Carey with Private Deck Space ❤️
Sleeps 8 · 3 bedrooms · 1 bathroom
8.68.6 out of 10
Excellentexcellent
23 reviews(23 reviews)
Bright, cozy city flat minutes from Oakland, Downtown Pittsburgh, PPG & Acrisure
Sleeps 6 · 2 bedrooms · 1 bathroom
7.07.0 out of 10
Goodgood
4 reviews(4 reviews)
Remodeled 3BR/1.5B, huge yard, off street pk
Sleeps 5 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Cozy Pittsburgh Home with King Beds - short drive to all
Sleeps 12 · 4 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
- 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, 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 accommodation in South Oakland?
The most popular types of holiday rentals in South Oakland are apartments. Searching for something different? Vrbo offers a variety of options to match our guests’ unique requirements, so you’ll see holiday properties in all shapes and sizes, and for all budgets. The perfect fit is ready and waiting for you — get hold of yours today.
How much does it cost to rent a holiday rental in South Oakland?
A number of things influence what you’ll pay for a holiday rental in South Oakland, like the type of property, length of stay and season. However, all our holiday homes have something in common — unbeatable value. Just enter your travel dates to find your ideal escape.
How much does it cost to rent a beach house in South Oakland?
Prices for beach houses in South Oakland will vary depending on the size and type of the property and time of year you’re travelling. Simply enter your travel dates into Vrbo and how many guests to see available options and prices. From there you can use our filters to narrow your search results by amenities, nearby activities, ratings and more.
Are there pet-friendly holiday rentals in South Oakland?
Pack up a suitcase for the pooch in your life because South Oakland has 24 holiday rentals that throw out the welcome mat to doggie guests. Let your furriest friend enjoy the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your dates then check the “Pets allowed” filter box.
What are popular rental amenities in South Oakland?
Off-street parking options, a balcony and high-speed internet services head the list of most popular rental amenities in South Oakland. Whether you’re planning to travel solo, with your significant other or a group of friends, Vrbo can help you find a holiday home that matches your tastes with all the features you’re looking for.
Are there large group holiday rentals in South Oakland?
With six South Oakland holiday rentals that can host five or more people, you can bring a few extra family members or pals along. Whether you’re planning a casual get-together or a special celebration, Vrbo will help you find the ideal space to match the occasion.
Are there holiday rentals in South Oakland that welcome kids?
Bring the entire family together for an epic adventure in South Oakland at one of our 24 family-friendly holiday homes. Many of these stays come with conveniences that are perfect for trips with children, such as laundries, living rooms and entertainment units. Simply click on the “Properties good for families” filter box and pick your favourite.
What are the top attractions for families in South Oakland?
Keeping the kiddos entertained during your South Oakland holiday is easy with these awesome family-friendly attractions:
- Pittsburgh Zoo and PPG Aquarium
- Carnegie Science Centre
- Carnegie Museum of Natural History
Are there one-bedroom holiday rentals in South Oakland?
Yes, you can pick from six one-bedroom rentals in South Oakland. Whether you’d prefer a townhouse or an upmarket condo, Vrbo’s one-bedroom properties are just right if you don’t require tons of space. One of the perks of having your own place? You won’t ever have to share your adventure with strangers.
Can I find two-bedroom holiday rentals in South Oakland?
South Oakland has 11 two-bedroom holiday properties for you to pick from. Go for a holiday home with all the comfort and privacy you want at an attractive price on Vrbo.
How can I find holiday rentals with air conditioning in South Oakland?
Work out your travel dates and then use the filter tool to locate holiday rentals with ac in South Oakland on Vrbo. With 22 air-conditioned properties on offer here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a holiday rental in South Oakland?
The minimum required age is normally 16, 18 or 21. It can vary from property to property on Vrbo, so look at the rules of your preferred South Oakland holiday home before booking your escape.
How long can I rent a holiday rental in South Oakland for?
The amount of time you can book a South Oakland holiday rental for is up to the property. Just tap in your preferred travel dates to find options offering extended stays. They come with all the things you need to make your extended trip more enjoyable and convenient, such as air conditioning and kitchens. Some holiday homes might also offer weekly or monthly discounted prices, so you can stay longer for less money.