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

South Side Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for South Side holiday rentals

A compact kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dishwasher.

1. Carey Way Quarters - Explorer's Dream Pad

Carey Way Quarters - Explorer's Dream Pad
South Side Flats
4.0 out of 10, (1 review)
The price is HK$588
HK$1,084 total
includes taxes & fees
10 Nov - 11 Nov
Carey Way Quarters - Explorer's Dream Pad
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

2. Carey Way Quarters – Modern 2BR Near Carson Street

Carey Way Quarters – Modern 2BR Near Carson Street
South Side Flats
9.2 out of 10, Wonderful, (15 reviews)
"Great location and property"
United States
Corey E.
The price is HK$839
HK$1,536 total
includes taxes & fees
7 Nov - 8 Nov
Carey Way Quarters – Modern 2BR Near Carson Street
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 HK$851
HK$1,716 total
includes taxes & fees
7 Nov - 8 Nov
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
A modern living room with a sectional sofa, a dark coffee table, and a world map on the wall.

4. 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 HK$811
HK$2,020 total
includes taxes & fees
9 Nov - 10 Nov
Iron City of South Side Flats Charming 2-bedroom Unit
Private kitchen

5. 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 HK$840
HK$2,052 total
includes taxes & fees
9 Nov - 10 Nov
Steel City of South Side Flats Charming 2-Bedroom Unit
A modern kitchen with a brick wall, white bar stools, and a dining area with a grey sofa.

6. Cozy&Modern 2Bdr Apt PIttsburgh

Cozy&Modern 2Bdr Apt PIttsburgh
South Side Flats
10.0 out of 10, Exceptional, (20 reviews)
"Great location, very clean, and exactly as described. We had a wonderful stay and would definitely stay here again! "
United States
Abby S.
The price is HK$949
HK$1,123 total
includes taxes & fees
9 Nov - 10 Nov
Cozy&Modern 2Bdr Apt PIttsburgh
A modern kitchen with stainless steel appliances, a dining area with a table and chairs, and a hallway leading to the kitchen.

7. 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 HK$1,105
HK$3,441 total
includes taxes & fees
22 Nov - 23 Nov
3bd 2bath House + Free Parking
A dining area with a round table, white chairs, a hanging light fixture, a radiator, and a colorful cityscape painting on the wall.

8. 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 HK$917
HK$1,640 total
includes taxes & fees
9 Nov - 10 Nov
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
An outdoor dining area with a wooden table and black chairs, surrounded by string lights and a white pergola.

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.
The price is HK$862
HK$2,062 total
includes taxes & fees
30 Nov - 1 Dec
Pittsburgh Pennsylvania house
A modern kitchen with white cabinets, a stainless steel dishwasher, a microwave, and a black countertop.

10. 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 HK$784
HK$2,402 total
includes taxes & fees
8 Nov - 9 Nov
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
An outdoor deck with a fire feature, seating, and a view of the city at night.

11. 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.
The price is HK$1,005
HK$3,409 total
includes taxes & fees
8 Nov - 9 Nov
City Skyline - Outside decks - Contemporary
A hallway with wooden doors leading to a bedroom with a bed and a ceiling fan.

12. 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 HK$529
HK$1,195 total
includes taxes & fees
8 Nov - 9 Nov
Cozy Loft Studio in a Triplex, near SouthSideWorks
A neatly made bed with a unique towel arrangement, a headboard, and a decorative wall piece.

13. *Historic Gem* Heart of Southside-Sleeps 10

*Historic Gem* Heart of Southside-Sleeps 10
South Side Flats
8.8 out of 10, Excellent, (33 reviews)
"The place exceeded my wildest expectations. I would highly recommend this hidden gem to anyone looking to stay on the South side"
United States
hans e.
The price is HK$1,380
HK$2,319 total
includes taxes & fees
9 Nov - 10 Nov
*Historic Gem* Heart of Southside-Sleeps 10
A row of brick townhouses with front porches, a small garden, and a visible mailbox.

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 HK$2,264
HK$4,633 total
includes taxes & fees
8 Nov - 9 Nov
Central 5BD Getaway - Spacious Home w/ BBQ
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)
"My family loved the walkable neighborhood and the hot tub and the hours spent at nearby Kennywood Park!"
United States
Joyce W.
The price is HK$4,358
HK$5,869 total
includes taxes & fees
12 Nov - 13 Nov
Pittsburgh House with Hot Tub, Patio & Free Parking!
A modern kitchen with dark cabinets, stainless steel appliances, a central island with stools, and a chandelier.

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, (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 HK$3,021
HK$5,064 total
includes taxes & fees
22 Nov - 23 Nov
King Bed | Free Parking | BBQ | Fire pit | Arcade
A wooden deck with potted plants and a hanging fern.

17. 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)
"Terrific stay at this South Side place! Cortney was super easy to work with and had great communication! Every detail in the home was very thought out; the rooms were clean, the beds comfortable and I will not hesitate to look for availability here any time we visit Pittsburgh! The neighborhood has a ton within walking distance; the coffee shop next door is amazing, and having 2 parking spots is priceless! Thank you!"
United States
Carol B.
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
A modern kitchen with a cityscape view, a brick accent wall, and a small island with seating.

18. Charming 1-Bedroom Apartment in Lovely Pittsburgh With AC

Charming 1-Bedroom Apartment in Lovely Pittsburgh With AC
Bluff
10.0 out of 10, Exceptional, (21 reviews)
"Great stay! Nice and clean, good location to walk downtown, quick communication from host. Definitely recommend!"
Canada
kasey
The price is HK$448
HK$1,134 total
includes taxes & fees
9 Nov - 10 Nov
Charming 1-Bedroom Apartment in Lovely Pittsburgh With AC
A grand banquet hall with high ceilings, ornate columns, and a central stage. Tables are set for a formal event, with floral centerpieces and elegant table settings.

19. Abode Pittsburgh - Downtown Convention Center

Abode Pittsburgh - Downtown Convention Center
3.5 star property
Downtown Pittsburgh
7.4 out of 10, Good, (102 reviews)
"Great location and room was clean! Bed was comfortable and kids slept just fine on the sleeper sofa. Very cool place too."
United States
Tiffany
The price is HK$402
HK$1,343 total
includes taxes & fees
18 Nov - 19 Nov
Abode Pittsburgh - Downtown Convention Center
A historic building with a large arched entrance, multiple windows, and a clock tower.

20. Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian
4.0 star property
Downtown Pittsburgh
8.8 out of 10, Excellent, (332 reviews)
"Great stay"
United States
Brandon
The price is HK$934
HK$1,065 total
includes taxes & fees
17 Nov - 18 Nov
Placemakr Downtown Pittsburgh at The Pennsylvanian
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
"Always a great experience"
Jennifer 1-night trip
Posted 2 hours ago
Wyndham Grand Pittsburgh Downtown

Find out more about South Side

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