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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for South Side vacation homes

A modern building with a curved glass facade, a waterfront view, and a landscaped area with trees.

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

Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi
South Side Slopes
Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi
A modern building with a curved glass facade, a waterfront view, and a city skyline in the background.

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

Spacious 2BR South Side Retreat | Free Parking | Fast WiFi
South Side Slopes
The price is AED 371
AED 807 total
includes taxes & fees
1 Nov - 2 Nov
Spacious 2BR South Side Retreat | Free Parking | Fast WiFi
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
9.8 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 AED 313
AED 753 total
includes taxes & fees
2 Nov - 3 Nov
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
A modern building with a curved glass facade, a waterfront view, and a city skyline in the background.

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

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

5. 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, (13 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 AED 551
AED 1,220 total
includes taxes & fees
29 Nov - 30 Nov
Iron City of South Side Flats Charming 2-bedroom Unit
Private kitchen

6. 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 AED 374
AED 1,017 total
includes taxes & fees
4 Nov - 5 Nov
Steel City of South Side Flats Charming 2-Bedroom Unit
A dining area with a round table, white chairs, a hanging light fixture, a radiator, and a colorful cityscape painting on the wall.

7. 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 AED 430
AED 843 total
includes taxes & fees
2 Nov - 3 Nov
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
A modern building with a curved glass facade, a waterfront view, and a landscaped area with trees.

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

Spacious 3BR South Side Retreat | Free Parking | Sleeps 6
South Side Slopes
The price is AED 606
AED 1,214 total
includes taxes & fees
14 Nov - 15 Nov
Spacious 3BR South Side Retreat | Free Parking | Sleeps 6
A dining area with a table and chairs, a potted plant, and a wall-mounted light fixture.

9. 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 AED 353
AED 1,460 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Centralized 3bd 2bath House w/ Free Parking
An outdoor deck with a fire feature, seating, and a view of the city at night.

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
An outdoor dining area with a wooden table and black chairs, surrounded by string lights and a white pergola.

11. 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 AED 396
AED 1,008 total
includes taxes & fees
3 Nov - 4 Nov
Pittsburgh Pennsylvania house
A modern kitchen with white cabinets, a stainless steel dishwasher, a microwave, and a black countertop.

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

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Allentown
9.6 out of 10, Exceptional, (5 reviews)
"Very nice place perfect for my needs."
United States
John
The price is AED 367
AED 1,173 total
includes taxes & fees
2 Nov - 3 Nov
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
A hallway with wooden doors leading to a bedroom with a bed and a ceiling fan.

13. 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 AED 248
AED 592 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Loft Studio in a Triplex, near SouthSideWorks
A city skyline with a view of various buildings, including a prominent UPMC building.

14. 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 AED 832
AED 1,765 total
includes taxes & fees
2 Nov - 3 Nov
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
A dining area with a long table set for a meal, a colorful abstract wall, and a retro arcade machine in the background.

15. 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.
Pittsburgh House with Hot Tub, Patio & Free Parking!
A wooden deck with potted plants and a hanging fern.

16. 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 AED 1,330
AED 2,431 total
includes taxes & fees
5 Nov - 6 Nov
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
A modern kitchen with dark cabinets, stainless steel appliances, a central island with stools, and a chandelier.

17. 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, (70 reviews)
"Great location and an amazing value"
United States
Tony J.
King Bed | Free Parking | BBQ | Fire pit | Arcade
A spacious living area with a wooden staircase, a ceiling fan, a dining table, and a kitchen area.

18. South Side Pittsburgh - Sleeps 9 - 4BR

South Side Pittsburgh - Sleeps 9 - 4BR
South Side Flats
South Side Pittsburgh - Sleeps 9 - 4BR
A living room with a fireplace, two armchairs, a sofa, and a patterned rug.

19. 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)
"we pretty much just traveled from appointments back to the house. but we were very well pleased with our accommodations"
United States
Kay K.
Relax & Feel At Home During Your Pittsburgh Stay
A cityscape with a river, a bridge, and a pedestrian walkway.

20. Urban Retreat with Garage on Mt. Washington

Urban Retreat with Garage on Mt. Washington
Mount Washington
9.8 out of 10, Exceptional, (100 reviews)
"Accurate pictures, very clean! Easy check in !! Will definitely stay Again!!"
United States
Jeff D.
The price is AED 367
AED 773 total
includes taxes & fees
2 Nov - 3 Nov
Urban Retreat with Garage on Mt. Washington
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

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

8/10 Good
"Valet most helpful. Clean room."
Julia 2-night trip
Posted 10 hours ago
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

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