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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for South Side vacation homes

Interior

1. 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 313
AED 757 total
includes taxes & fees
14 Oct - 15 Oct
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
Smart TV

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

Iron City of South Side Flats Charming 2-bedroom Unit
South Side Flats
9.8 out of 10, Exceptional, (10 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 314
AED 942 total
includes taxes & fees
21 Sep - 22 Sep
Iron City of South Side Flats Charming 2-bedroom Unit
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.
Steel City of South Side Flats Charming 2-Bedroom Unit
Private kitchen

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

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Allentown
10.0 out of 10, Exceptional, (1 review)
"Very nice place perfect for my needs."
United States
John
The price is AED 367
AED 1,056 total
includes taxes & fees
28 Sep - 29 Sep
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
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 479
AED 1,465 total
includes taxes & fees
21 Sep - 22 Sep
City Skyline - Outside decks - Contemporary
Dining

6. 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.
Cozy Centralized 3bd 2bath House w/ Free Parking
1 bedroom, in-room safe, desk, iron/ironing board

7. 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
20 Sep - 21 Sep
Cozy Loft Studio in a Triplex, near SouthSideWorks
Dining

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 AED 463
AED 881 total
includes taxes & fees
6 Oct - 7 Oct
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
Outdoor dining

9. 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.
Pittsburgh Pennsylvania house
Coffee/tea maker, fridge, microwave, oven

10. 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
Coffee/tea maker, fridge, microwave, oven

11. 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.
The price is AED 1,429
AED 2,520 total
includes taxes & fees
20 Sep - 21 Sep
King Bed | Free Parking | BBQ | Fire pit | Arcade
Property grounds

12. 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.
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
Terrace/patio

13. 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)
"I had an excellent stay at this property and would definitely stay here again. The home was comfortable and stylish. The bedding, towels, and linens were fresh, soft, and comfortable. The neighborhood was charming, walkable, and conveniently located in relation to restaurants and other attractions. The host was also very responsive to questions."
United States
Karin
The price is AED 2,083
AED 3,082 total
includes taxes & fees
11 Oct - 12 Oct
Pittsburgh House with Hot Tub, Patio & Free Parking!
Coffee/tea maker, fridge, microwave, oven

14. 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, (44 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 AED 1,561
AED 2,527 total
includes taxes & fees
11 Oct - 12 Oct
Clean and comfortable 3BR home in the South Side neighborhood
Property grounds

15. Pittsburgh Gem - 5BR - Downtown Deck View

Pittsburgh Gem - 5BR - Downtown Deck View
South Side Flats
9.8 out of 10, Exceptional, (8 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.
Pittsburgh Gem - 5BR - Downtown Deck View
Outdoor dining

16. Southside Gem w Hot Tub and Dedicated Parking

Southside Gem w Hot Tub and Dedicated Parking
South Side Slopes
The price is AED 2,530
AED 4,309 total
includes taxes & fees
8 Oct - 9 Oct
Southside Gem w Hot Tub and Dedicated Parking
Property grounds

17. 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 731 total
includes taxes & fees
13 Oct - 14 Oct
Urban Retreat with Garage on Mt. Washington
Interior

18. 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 301
AED 849 total
includes taxes & fees
21 Sep - 22 Sep
1209 Ocala St Pittsburgh
Interior

19. 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, (48 reviews)
"Great location and very comfortable beds!"
United States
Cassi D.
The price is AED 303
AED 702 total
includes taxes & fees
21 Sep - 22 Sep
307 37th St · Lawrenceville Row House - Walk to Everything!
Property grounds

20. Explore Pittsburgh from a Modern, Hip Bungalow

Explore Pittsburgh from a Modern, Hip Bungalow
North Side
9.6 out of 10, Exceptional, (73 reviews)
"Great location. Would stay again. "
United States
Yukiko M.
The price is AED 257
AED 686 total
includes taxes & fees
4 Oct - 5 Oct
Explore Pittsburgh from a Modern, Hip Bungalow
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

Pittsburgh Airport Inn and Suites

Pittsburgh Airport Inn and Suites

10/10 Excellent
"The room included a sofa for relaxing. Nice to have space to unwind. Will use the park and fly option next time."
judy 1-night trip
Posted 2 hours ago
Pittsburgh Airport Inn and Suites

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