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Our top choices for South Side vacation homes

1. Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi

Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi
South Side Slopes
The price is ¥11,569
¥26,778 total
includes taxes & fees
Nov 21 - Nov 22
Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi

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, (14 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 ¥16,403
¥40,834 total
includes taxes & fees
Nov 9 - Nov 10
Iron City of South Side Flats Charming 2-bedroom Unit

3. 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, (5 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 ¥16,545
¥42,689 total
includes taxes & fees
Nov 10 - Nov 11
Steel City of South Side Flats Charming 2-Bedroom Unit

4. 3bd 2bath House + Free Parking

3bd 2bath House + 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 ¥14,718
¥60,031 total
includes taxes & fees
Dec 1 - Dec 2
3bd 2bath House + Free Parking

5. 3-bedroom house in Southside Flats neighborhood of Pittsburgh.

3-bedroom house in Southside Flats neighborhood of Pittsburgh.
South Side Flats
8.0 out of 10, Very good, (3 reviews)
"Place was close to everything ee need the beds and kitchen was clean and the host was very helpful and the check in process was quick and easy"
United States
Alex C.
The price is ¥18,542
¥33,165 total
includes taxes & fees
Nov 9 - Nov 10
3-bedroom house in Southside Flats neighborhood of Pittsburgh.

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

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
South Side Flats
9.8 out of 10, Exceptional, (6 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 ¥19,141
¥37,067 total
includes taxes & fees
Nov 11 - Nov 12
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

7. Spacious 3BR South Side Retreat | Free Parking | Sleeps 6

Spacious 3BR South Side Retreat | Free Parking | Sleeps 6
South Side Slopes
The price is ¥16,640
¥38,662 total
includes taxes & fees
Nov 21 - Nov 22
Spacious 3BR South Side Retreat | Free Parking | Sleeps 6

8. 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 ¥17,433
¥41,692 total
includes taxes & fees
Nov 30 - Dec 1
Pittsburgh Pennsylvania house

9. Sleeps 10 · Walk to Carson St · BBQ & Fire Pit

Sleeps 10 · Walk to Carson St · BBQ & Fire Pit
South Side Flats
The price is ¥22,441
¥59,315 total
includes taxes & fees
Nov 9 - Nov 10
Sleeps 10 · Walk to Carson St · BBQ & Fire Pit

10. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay in this beautiful home! The host was super responsive and helpful. The home is spacious and well kept with amazing views of the city. The cherry on top was the driveway/parking area that accommodated our five vehicles. Great choice for our family get together!"
United States
Mary H.
City Skyline - Outside decks - Contemporary

11. Cozy Loft Studio in a Triplex, near SouthSideWorks

Cozy Loft Studio in a Triplex, near SouthSideWorks
South Side Flats
8.0 out of 10, Very good, (2 reviews)
"Great communication"
United States
Clay B.
The price is ¥10,697
¥22,981 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Loft Studio in a Triplex, near SouthSideWorks

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

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Allentown
9.8 out of 10, Exceptional, (6 reviews)
"Very nice place perfect for my needs."
United States
John
The price is ¥15,848
¥46,693 total
includes taxes & fees
Nov 9 - Nov 10
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

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

Central 5BD Getaway - Spacious Home w/ BBQ
South Side Flats
10.0 out of 10, Exceptional, (12 reviews)
"Great host and property "
United States
Eric G.
The price is ¥45,763
¥90,283 total
includes taxes & fees
Nov 9 - Nov 10
Central 5BD Getaway - Spacious Home w/ BBQ

14. King Bed | Free Parking | BBQ | Fire pit | Arcade

King Bed | Free Parking | BBQ | Fire pit | Arcade
South Side Flats
9.8 out of 10, Exceptional, (71 reviews)
"This property was amazing! The Southside Flats area is a great location! Brandon the host was very responsive to questions and concerns prior to and during our stay. The backyard patio was a nice feature! The appliances were top notch! It had an elegant Bohemian feel to it! Will definitely book in the future."
United States
Agnes C.
The price is ¥53,890
¥94,507 total
includes taxes & fees
Nov 22 - Nov 23
King Bed | Free Parking | BBQ | Fire pit | Arcade

15. Urban Retreat with Garage on Mt. Washington

Urban Retreat with Garage on Mt. Washington
Mount Washington
9.8 out of 10, Exceptional, (101 reviews)
"it was perfect for our trip thank you for sharing"
United States
James S.
The price is ¥15,056
¥29,925 total
includes taxes & fees
Nov 9 - Nov 10
Urban Retreat with Garage on Mt. Washington

16. Relax & Feel At Home During Your Pittsburgh Stay

Relax & Feel At Home During Your Pittsburgh Stay
Carrick
9.4 out of 10, Exceptional, (32 reviews)
"nice place to celebrate my Pitt grad!"
United States
Claudia T.
The price is ¥23,455
¥42,809 total
includes taxes & fees
Nov 28 - Nov 29
Relax & Feel At Home During Your Pittsburgh Stay

17. Spacious 4-BR Home – Open Concept, Deck & Parking!

Spacious 4-BR Home – Open Concept, Deck & Parking!
Mount Washington
9.0 out of 10, Wonderful, (67 reviews)
"Great home and location. Convenient location for downtown and surrounding areas."
United States
ejp133`
The price is ¥26,625
¥52,475 total
includes taxes & fees
Nov 14 - Nov 15
Spacious 4-BR Home – Open Concept, Deck & Parking!

18. Eclectic Historic Sunny Vista Home with City Views, Northshore

Eclectic Historic Sunny Vista Home with City Views, Northshore
North Side
9.6 out of 10, Exceptional, (43 reviews)
"Great location! Close proximity to the city, but secluded in the mountain. Great place to stay for a series at PNC park."
United States
Alli S.
The price is ¥12,520
¥32,004 total
includes taxes & fees
Nov 10 - Nov 11
Eclectic Historic Sunny Vista Home with City Views, Northshore

19. Lovely Strip District loft with free parking

Lovely Strip District loft with free parking
Strip District
10.0 out of 10, Exceptional, (44 reviews)
"Perfect stay"
United States
M D.
The price is ¥17,116
¥28,206 total
includes taxes & fees
Nov 11 - Nov 12
Lovely Strip District loft with free parking

20. By PPG,Duquesne,Mercy |Exquisite, New |Free Parkin

By PPG,Duquesne,Mercy |Exquisite, New |Free Parkin
Bluff
10.0 out of 10, Exceptional, (19 reviews)
"Place was very nice, quite spacious and comfortable for our group. Very clean and bright - we enjoyed our stay. "
United States
Tom M.
The price is ¥34,216
¥72,500 total
includes taxes & fees
Nov 9 - Nov 10
By PPG,Duquesne,Mercy |Exquisite, New |Free Parkin
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.

Learn more about South Side

Stroll along East Carson Street, where vibrant murals and eclectic shops showcase the neighborhood's artistic spirit. Catch a show at the historic Rex Theater or savor Pittsburgh's famous 'fries on sandwiches' at Primanti Bros.

Large stainless steel brewing tanks with logos and text, set against a building with arched windows and a brick facade.

Top reviews in South Side

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