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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for South Side vacation homes

Smart TV

1. 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 AED 347
AED 983 total
includes taxes & fees
29 Sep - 30 Sep
Iron City of South Side Flats Charming 2-bedroom Unit
Dining

2. 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 459
AED 881 total
includes taxes & fees
6 Oct - 7 Oct
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
Private kitchen

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, (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 AED 367
AED 1,010 total
includes taxes & fees
6 Oct - 7 Oct
Steel City of South Side Flats Charming 2-Bedroom Unit
Interior

4. 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 AED 362
AED 817 total
includes taxes & fees
22 Oct - 23 Oct
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
Outdoor dining

5. 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.
The price is AED 522
AED 1,581 total
includes taxes & fees
30 Sep - 1 Oct
City Skyline - Outside decks - Contemporary
Private kitchen

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 AED 367
AED 1,064 total
includes taxes & fees
28 Sep - 29 Sep
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
TV, offices

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

Cozy South Side Retreat | Free Parking | Fast WiFi
South Side Slopes
The price is AED 327
AED 719 total
includes taxes & fees
1 Oct - 2 Oct
Cozy South Side Retreat | Free Parking | Fast WiFi
1 bedroom, in-room safe, desk, iron/ironing board

8. 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.
Cozy Loft Studio in a Triplex, near SouthSideWorks
Dining

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 505
AED 1,678 total
includes taxes & fees
21 Oct - 22 Oct
Cozy Centralized 3bd 2bath House w/ Free Parking
Exterior detail

10. 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 AED 2,125
AED 3,518 total
includes taxes & fees
27 Sep - 28 Sep
Central 5BD Getaway - Spacious Home w/ BBQ
Outdoor dining

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 412
AED 1,038 total
includes taxes & fees
5 Oct - 6 Oct
Pittsburgh Pennsylvania house
Property grounds

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, (4 reviews)
"Great stay! Rooms were comfortable and very clean. "
United States
Anonymous traveler
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
Property grounds

13. 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 1,316
AED 2,415 total
includes taxes & fees
1 Oct - 2 Oct
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
Coffee/tea maker, fridge, microwave, oven

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, (70 reviews)
"Great location and an amazing value"
United States
Tony J.
King Bed | Free Parking | BBQ | Fire pit | Arcade
Outdoor dining

15. Southside Gem w Hot Tub and Dedicated Parking

Southside Gem w Hot Tub and Dedicated Parking
South Side Slopes
Southside Gem w Hot Tub and Dedicated Parking
Property grounds

16. Urban Retreat with Garage on Mt. Washington

Urban Retreat with Garage on Mt. Washington
Mount Washington
9.8 out of 10, Exceptional, (95 reviews)
"Great place! Short walk to cool areas "
United States
David M.
The price is AED 327
AED 723 total
includes taxes & fees
19 Oct - 20 Oct
Urban Retreat with Garage on Mt. Washington
Interior

17. 307 37th St · Lawrenceville Row House - Walk to Everything!

307 37th St · Lawrenceville Row House - Walk to Everything!
Lawrenceville
9.4 out of 10, Exceptional, (49 reviews)
"Great location and very comfortable beds!"
United States
Cassi D.
The price is AED 263
AED 661 total
includes taxes & fees
5 Oct - 6 Oct
307 37th St · Lawrenceville Row House - Walk to Everything!
TV, stereo, computer monitors

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

Dog-Friendly Pittsburgh Home, 3 Mi to Downtown!
Mount Washington
8.6 out of 10, Excellent, (13 reviews)
"Good location to get near everything for game day."
United States
Zachary J.
The price is AED 147
AED 1,343 total
includes taxes & fees
1 Oct - 2 Oct
Dog-Friendly Pittsburgh Home, 3 Mi to Downtown!
Living area

19. Strip District Studio-Free Parking-Natural Light

Strip District Studio-Free Parking-Natural Light
Strip District
9.2 out of 10, Wonderful, (33 reviews)
"We had a great stay - it was a beautiful place and convenient location. It could get somewhat noisy, but we did not have any trouble sleeping through the night. Would stay again for another Pittsburgh trip!"
United States
Martene B.
Strip District Studio-Free Parking-Natural Light
Interior

20. 1209 Ocala St Pittsburgh

1209 Ocala St Pittsburgh
North Side
10.0 out of 10, Exceptional, (42 reviews)
"The house was very cool place - lots of interesting touches, very clean and had everything we needed.The host was so easy to communicate with and provided very clear instructions, which was very important regarding the parking.The location was also perfect - easy walking distance to PNC Park, the River Trail and other landmarks.We would definitely stay here again and are already looking forward to our next visit!!"
United States
Mary B.
The price is AED 368
AED 937 total
includes taxes & fees
12 Oct - 13 Oct
1209 Ocala St Pittsburgh
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

Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown

8/10 Good
"The property was well maintained but gives a very office space feel which isn’t very cozy but gets the job done. The staff were very helpful with anything we requested. The room was clean and newer."
Scott 1-night trip
Posted 5 hours ago
Drury Plaza Hotel Pittsburgh Downtown

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