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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 holiday 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
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 HK$671
HK$2,011 total
includes taxes & fees
30 Sept - 1 Oct
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 HK$1,017
HK$1,922 total
includes taxes & fees
30 Sept - 1 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 HK$819
HK$2,214 total
includes taxes & fees
5 Oct - 6 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 HK$1,028
HK$2,086 total
includes taxes & fees
28 Sept - 29 Sept
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.
City Skyline - Outside decks - Contemporary
Coffee/tea maker, fridge, microwave, oven

6. 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
Private kitchen

7. 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 HK$777
HK$2,247 total
includes taxes & fees
22 Sept - 23 Sept
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Dining

8. 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 HK$1,027
HK$3,541 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Centralized 3bd 2bath House w/ Free Parking
Exterior detail

9. 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 HK$1,305
HK$3,617 total
includes taxes & fees
22 Sept - 23 Sept
Central 5BD Getaway - Spacious Home w/ BBQ
1 bedroom, in-room safe, desk, iron/ironing board

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.
Cozy Loft Studio in a Triplex, near SouthSideWorks
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 HK$1,389
HK$2,876 total
includes taxes & fees
5 Oct - 6 Oct
Pittsburgh Pennsylvania house
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.
The price is HK$2,636
HK$4,867 total
includes taxes & fees
22 Sept - 23 Sept
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 HK$4,754
HK$6,972 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, (45 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 HK$3,334
HK$5,423 total
includes taxes & fees
11 Oct - 12 Oct
Clean and comfortable 3BR home in the South Side neighborhood
Outdoor dining

15. Southside Gem w Hot Tub and Dedicated Parking

Southside Gem w Hot Tub and Dedicated Parking
South Side Slopes
The price is HK$5,410
HK$9,209 total
includes taxes & fees
8 Oct - 9 Oct
Southside Gem w Hot Tub and Dedicated Parking
Coffee/tea maker, fridge, microwave, oven

16. 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 HK$4,785
HK$7,375 total
includes taxes & fees
25 Sept - 26 Sept
King Bed | Free Parking | BBQ | Fire pit | Arcade
TV, offices

17. 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
Property grounds

18. 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 HK$698
HK$1,495 total
includes taxes & fees
13 Oct - 14 Oct
Urban Retreat with Garage on Mt. Washington
Interior

19. 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 HK$644
HK$1,812 total
includes taxes & fees
22 Sept - 23 Sept
1209 Ocala St Pittsburgh
TV, offices

20. M&J - Emlin 513 St.

M&J - Emlin 513 St.
North Side
9.8 out of 10, Exceptional, (23 reviews)
"Great location / neighborhood and the host was very easy to work with and responsive "
United States
Gerrit v.
M&J - Emlin 513 St.
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

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

10/10 Excellent
"We had no issues. Will be staying here again. Only issue and that wasn't on the hotel. The parking across the street was a bit pricey."
David 1-night trip
Posted 1 hour ago
Wyndham Grand Pittsburgh Downtown

Find out more about South Side

South Side Vacation Homes information

Number of reviews
355
Accommodation
737 Vacation Homes
Lowest Price
HK$1,495
Highest Price
HK$9,209

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