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Our top choices for South Side vacation homes

1. 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.
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

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 ¥15,961
¥42,218 total
includes taxes & fees
Nov 18 - Nov 19
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 ¥16,249
¥42,547 total
includes taxes & fees
Nov 18 - Nov 19
Steel City of South Side Flats Charming 2-Bedroom Unit

4. 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 ¥21,569
¥38,252 total
includes taxes & fees
Nov 16 - Nov 17
3-bedroom house in Southside Flats neighborhood of Pittsburgh.

5. 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 ¥20,789
¥65,112 total
includes taxes & fees
Nov 23 - Nov 24
3bd 2bath House + Free Parking

6. King Bed | Garage Door Patio | Free Parking

King Bed | Garage Door Patio | Free Parking
South Side Flats
9.6 out of 10, Exceptional, (33 reviews)
"Great stay ! "
United States
Vidal R.
The price is ¥37,800
¥72,557 total
includes taxes & fees
Dec 2 - Dec 3
King Bed | Garage Door Patio | Free Parking

7. 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 ¥16,344
¥41,134 total
includes taxes & fees
Nov 16 - Nov 17
Pittsburgh Pennsylvania house

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

Sleeps 10 · Walk to Carson St · BBQ & Fire Pit
South Side Flats
The price is ¥22,623
¥60,822 total
includes taxes & fees
Nov 16 - Nov 17
Sleeps 10 · Walk to Carson St · BBQ & Fire Pit

9. 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 ¥15,977
¥49,295 total
includes taxes & fees
Nov 16 - Nov 17
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

10. 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 ¥10,784
¥24,364 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Loft Studio in a Triplex, near SouthSideWorks

11. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
10.0 out of 10, Exceptional, (12 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.
The price is ¥24,107
¥73,991 total
includes taxes & fees
Nov 15 - Nov 16
City Skyline - Outside decks - Contemporary

12. Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views

Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
South Side Slopes
10.0 out of 10, Exceptional, (7 reviews)
"Great stay! Rooms were comfortable and very clean. "
United States
Anonymous traveler
The price is ¥22,106
¥56,820 total
includes taxes & fees
Nov 16 - Nov 17
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views

13. Pittsburgh Gem - 5BR - Downtown Deck View

Pittsburgh Gem - 5BR - Downtown Deck View
South Side Flats
9.4 out of 10, Exceptional, (9 reviews)
"Perfect location for our family to stay for the Pitt graduation. Wish we knew about it 4 years ago because it would have been our go to place for visits!"
United States
Denise T.
The price is ¥70,913
¥125,795 total
includes taxes & fees
Nov 14 - Nov 15
Pittsburgh Gem - 5BR - Downtown Deck View

14. 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 ¥46,170
¥94,850 total
includes taxes & fees
Nov 15 - Nov 16
Central 5BD Getaway - Spacious Home w/ BBQ

15. 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 ¥52,471
¥88,659 total
includes taxes & fees
Nov 22 - Nov 23
King Bed | Free Parking | BBQ | Fire pit | Arcade

16. Urban Retreat with Garage on Mt. Washington

Urban Retreat with Garage on Mt. Washington
Mount Washington
9.8 out of 10, Exceptional, (103 reviews)
"it was perfect for our trip thank you for sharing"
United States
James S.
The price is ¥14,220
¥30,272 total
includes taxes & fees
Nov 18 - Nov 19
Urban Retreat with Garage on Mt. Washington

17. 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.
Relax & Feel At Home During Your Pittsburgh Stay

18. Dog-Friendly Pittsburgh Home, 3 Mi to Downtown!

Dog-Friendly Pittsburgh Home, 3 Mi to Downtown!
Mount Washington
8.2 out of 10, Very good, (14 reviews)
"Good location to get near everything for game day."
United States
Zachary J.
The price is ¥20,626
¥104,840 total
includes taxes & fees
Nov 24 - Nov 25
Dog-Friendly Pittsburgh Home, 3 Mi to Downtown!

19. 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 ¥13,271
¥32,846 total
includes taxes & fees
Nov 15 - Nov 16
Eclectic Historic Sunny Vista Home with City Views, Northshore
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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