A park with autumn trees, a bridge, and a building labeled UPMC in the background.

South Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for South Side vacation rentals

A bedroom with a bed, bedside tables, a mirror, and a door.

1. Spacious 2BR South Side Retreat | Free Parking | Fast WiFi

Spacious 2BR South Side Retreat | Free Parking | Fast WiFi
South Side Slopes
The price is ￥18,874
￥37,464 total
includes taxes & fees
Oct 1 - Oct 2
Spacious 2BR South Side Retreat | Free Parking | Fast WiFi
A modern living room with a sectional sofa, a dark coffee table, and a world map on the wall.

2. Iron City of South Side Flats Charming 2-bedroom Unit

Iron City of South Side Flats Charming 2-bedroom Unit
South Side Flats
10.0 out of 10, Exceptional, (11 reviews)
"Excellent property. Very convenient having on-site parking. Super clean, cozy, comfortable and well located. Will stay again this upcoming weekend!"
United States
Manuel M.
The price is ￥16,420
￥42,703 total
includes taxes & fees
Sep 30 - Oct 1
Iron City of South Side Flats Charming 2-bedroom Unit
A living room with a fireplace, a television, and a dining area with a table and chairs.

3. HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
South Side Flats
9.6 out of 10, Exceptional, (5 reviews)
"The property was outstanding, nicely appointed and quite comfortable. Close to downtown without being IN downtown, thus very well-located for everywhere we needed to be. Service was excellent, our questions were answered promptly and with the right amount of detail. "
United States
Butch K.
The price is ￥15,502
￥34,486 total
includes taxes & fees
Oct 5 - Oct 6
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
Private kitchen

4. Steel City of South Side Flats Charming 2-Bedroom Unit

Steel City of South Side Flats Charming 2-Bedroom Unit
South Side Flats
10.0 out of 10, Exceptional, (4 reviews)
"Great location, appreciated off-street gated parking at residence. Unit is updated and clean with lots of modern amenities. Had a great visit, would definitely stay here again."
United States
Heather B.
The price is ￥17,694
￥44,158 total
includes taxes & fees
Oct 6 - Oct 7
Steel City of South Side Flats Charming 2-Bedroom Unit
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with wicker chairs and a round table.

5. 2615 Jane Down - Southside

2615 Jane Down - Southside
South Side Flats
8.6 out of 10, Excellent, (4 reviews)
"Very clean modern place in nice neighborhood. Location great for walking. Found a vegan restaurant less than two blocks away. "
United States
Bertha T.
The price is ￥11,117
￥30,205 total
includes taxes & fees
Oct 21 - Oct 22
2615 Jane Down - Southside
A modern kitchen with white cabinets, a stainless steel dishwasher, a microwave, and a black countertop.

6. Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Allentown
9.4 out of 10, Exceptional, (3 reviews)
"Very nice place perfect for my needs."
United States
John
The price is ￥15,728
￥43,708 total
includes taxes & fees
Sep 30 - Oct 1
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
A compact kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dishwasher.

7. Carey Way Quarters - Explorer's Dream Pad

Carey Way Quarters - Explorer's Dream Pad
South Side Flats
The price is ￥10,852
￥22,028 total
includes taxes & fees
Oct 8 - Oct 9
Carey Way Quarters - Explorer's Dream Pad
A dining area with a round table, white chairs, a hanging light fixture, a radiator, and a colorful cityscape painting on the wall.

8. 3-bedroom house in Southside Flats neighborhood of Pittsburgh.

3-bedroom house in Southside Flats neighborhood of Pittsburgh.
South Side Flats
7.0 out of 10, Good, (2 reviews)
"The house was very spacious! Everyone slept comfortably. The house is very conveniently located giving you the ability to access food on Carson as well as the highway."
United States
Kyle S.
The price is ￥18,700
￥35,455 total
includes taxes & fees
Oct 20 - Oct 21
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
An outdoor deck with a fire feature, seating, and a view of the city at night.

9. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
9.8 out of 10, Exceptional, (9 reviews)
"House was perfect for our small gathering of family and friends. We lived out on the decks where the view is spectacular. Host could not have been better. Thanks for a perfect stay!"
United States
Glen C.
City Skyline - Outside decks - Contemporary
A living room with a sectional sofa, a coffee table, a patterned rug, and a wall-mounted airplane artwork.

10. Cozy South Side Retreat | Free Parking | Fast WiFi

Cozy South Side Retreat | Free Parking | Fast WiFi
South Side Slopes
The price is ￥14,312
￥30,981 total
includes taxes & fees
Oct 1 - Oct 2
Cozy South Side Retreat | Free Parking | Fast WiFi
A modern kitchen with grey cabinets, a stainless steel dishwasher, a microwave, and wooden shelves with decorative items.

11. Industrial Chic Studio-Modern Comfort in the Burgh

Industrial Chic Studio-Modern Comfort in the Burgh
South Side Flats
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay. Easy access to bridges which then led us to Pitt to visit. Owner was very responsive to our questions. We'd stay here again!"
United States
Rich D.
The price is ￥25,008
￥38,166 total
includes taxes & fees
Oct 11 - Oct 12
Industrial Chic Studio-Modern Comfort in the Burgh
A neatly made bed with a unique towel arrangement, a headboard, and a decorative wall piece.

12. *Historic Gem* Heart of Southside-Sleeps 10

*Historic Gem* Heart of Southside-Sleeps 10
South Side Flats
9.0 out of 10, Wonderful, (32 reviews)
"The place exceeded my wildest expectations. I would highly recommend this hidden gem to anyone looking to stay on the South side"
United States
hans e.
The price is ￥27,996
￥48,729 total
includes taxes & fees
Oct 1 - Oct 2
*Historic Gem* Heart of Southside-Sleeps 10
A spice rack with labeled containers for sea salt, parsley, celery salt, and mint.

13. Cozy Centralized 3bd 2bath House w/ Free Parking

Cozy Centralized 3bd 2bath House w/ Free Parking
South Side Flats
7.0 out of 10, Good, (2 reviews)
"We had a wonderful stay and would absolutely book this property again. The home was clean, comfortable, and exactly as described, with everything we needed for a relaxing trip. The host was responsive, helpful, and made the whole experience easy from start to finish. Great location, thoughtful touches, and a smooth check-in/check-out process made this a fantastic stay. Highly recommend!"
United States
Mark W.
The price is ￥39,320
￥89,319 total
includes taxes & fees
Oct 4 - Oct 5
Cozy Centralized 3bd 2bath House w/ Free Parking
An outdoor dining area with a wooden table and black chairs, surrounded by string lights and a white pergola.

14. Pittsburgh Pennsylvania house

Pittsburgh Pennsylvania house
South Side Flats
6.0 out of 10, (2 reviews)
"Great 3 bed, 1 bathroom place to stay in Southside Pittsburgh. One block walk to E Carson St. Be sure to bring your own bath towels and soap."
United States
Adrian C.
The price is ￥17,820
￥42,644 total
includes taxes & fees
Oct 20 - Oct 21
Pittsburgh Pennsylvania house
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

15. Carey Way Quarters – Modern 2BR Near Carson Street

Carey Way Quarters – Modern 2BR Near Carson Street
South Side Flats
9.0 out of 10, Wonderful, (14 reviews)
"Great location and property"
United States
Corey E.
The price is ￥25,008
￥41,312 total
includes taxes & fees
Oct 11 - Oct 12
Carey Way Quarters – Modern 2BR Near Carson Street
A living room with a blue sofa, a coffee table, and a painting of a sunset.

16. Birmingham Bridge Beauty Cozy Stay Near Downtown

Birmingham Bridge Beauty Cozy Stay Near Downtown
South Side Flats
2.0 out of 10, (1 review)
"While the host was responsive when requested, the check-in link provided with pictures was not live, making check-in confusing especially in the dark when we didn’t know the entrance was on the side of the building. The property is basic with no charm or comfort commodities which are usually found in a rental property such as this. There are two doors from the unit that gain access to other areas of the house that, while are locked to prevent people from gaining access to the apartment, they are...
United States
Laura
The price is ￥18,874
￥32,746 total
includes taxes & fees
Oct 11 - Oct 12
Birmingham Bridge Beauty Cozy Stay Near Downtown
A row of brick townhouses with front porches, a small garden, and a visible mailbox.

17. Central 5BD Getaway - Spacious Home w/ BBQ

Central 5BD Getaway - Spacious Home w/ BBQ
South Side Flats
10.0 out of 10, Exceptional, (11 reviews)
"Stayed for a guys weekend with the family, everybody was very happy with the accommodations and the proximity to restaurants and such. Phil and Dotty were two of the most gracious responsive hosts I’ve ever had the pleasure of dealing with. Would def rent again if back in Pittsburgh"
United States
Sean O.
The price is ￥30,941
￥74,476 total
includes taxes & fees
Sep 30 - Oct 1
Central 5BD Getaway - Spacious Home w/ BBQ
A wooden deck with potted plants and a hanging fern.

18. Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
South Side Flats
10.0 out of 10, Exceptional, (22 reviews)
"Fantastic property. Intriguing history. Great location."
United States
Kevin M.
The price is ￥51,525
￥90,850 total
includes taxes & fees
Oct 1 - Oct 2
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
A backyard with a fire pit, a white chair, a colorful wall, and a wooden fence.

19. Pittsburgh House with Hot Tub, Patio & Free Parking!

Pittsburgh House with Hot Tub, Patio & Free Parking!
South Side Flats
10.0 out of 10, Exceptional, (8 reviews)
"Perfect vibes for a small girls trip. Great location. Such a fun place, thanks for the small details!"
United States
Sara P.
The price is ￥85,718
￥121,093 total
includes taxes & fees
Oct 11 - Oct 12
Pittsburgh House with Hot Tub, Patio & Free Parking!
A modern kitchen with white cabinets, stainless steel appliances, and a central island with a basket of decorative items.

20. Clean and comfortable 3BR home in the South Side neighborhood

Clean and comfortable 3BR home in the South Side neighborhood
South Side Slopes
10.0 out of 10, Exceptional, (45 reviews)
"This is such a cute house that is close to downtown. 10/10 would recommend this house. It was perfect for us!"
United States
Amanda R.
The price is ￥66,844
￥102,993 total
includes taxes & fees
Oct 11 - Oct 12
Clean and comfortable 3BR home in the South Side neighborhood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Side Hotel Reviews

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

10/10 Excellent
"Everything was great. Great service and the hotel is close to restaurants and bars with great foods."
Alvaro 3-night trip
Posted 3 hours ago
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

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