South Side Holiday Rentals

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Check prices for these dates

Tonight
19 Dec - 20 Dec
Tomorrow
20 Dec - 21 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for South Side holiday rentals

Exterior
Kasa South Side Pittsburgh

Aparthotel in South Side Flats

Kasa South Side Pittsburgh
4.0 star property
8.2 out of 10, Very good, (105)
"Clean great views hotel "
United States
Shomario
The price is HK$966
HK$1,607 total
includes taxes & fees
4 Jan - 5 Jan 2026
Kasa South Side Pittsburgh
Outdoor dining
Clean & Central Pittsburgh Retreat • Cozy + Highly Walkable!

Holiday Home in South Side Flats

Clean & Central Pittsburgh Retreat • Cozy + Highly Walkable!
8.0 out of 10, Very good, (6)
"Excellent communication with owner. Fast, friendly and courteous. Located about 450 meter walk up a large hill from Penn Avenue (bus 88) which is about 35 minutes to downtown. Apartment showing its age but fair value for cost. "
Canada
Jarrod
Clean & Central Pittsburgh Retreat • Cozy + Highly Walkable!
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Cozy&Modern 2Bdr Apt PIttsburgh

Apartment in South Side Flats

Cozy&Modern 2Bdr Apt PIttsburgh
2.0 star property
10.0 out of 10, Exceptional, (10)
"Great spot!"
United States
Kevin D.
Cozy&Modern 2Bdr Apt PIttsburgh
Front of property
Walkable Studio in the Heart of Pittsburgh!

Apartment in South Side Flats

Walkable Studio in the Heart of Pittsburgh!
3.0 star property
2.0 out of 10, (1)
"A Complete Dump! Did not stay!"
United States
John
Walkable Studio in the Heart of Pittsburgh!
Fridge, microwave, oven, stovetop
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

Holiday Home in South Side Flats

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
7.8 out of 10, Good, (8)
"Home was very comfy children enjoyed there stay I was able to relax and feel comfortable stay I would definitely book again."
United States
bonita f.
The price is HK$350
HK$1,902 total
includes taxes & fees
21 Dec - 22 Dec
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
Exterior
Placemakr Downtown Pittsburgh at The Pennsylvanian

Apartment in Downtown Pittsburgh

Placemakr Downtown Pittsburgh at The Pennsylvanian
4.0 star property
7.8 out of 10, Good, (47)
"I had a wonderful stay, very quiet and clean "
United States
Leslie
The price is HK$1,035
HK$1,180 total
includes taxes & fees
28 Dec - 29 Dec
Placemakr Downtown Pittsburgh at The Pennsylvanian
Front of property
Stay Pittsburgh

Aparthotel in Downtown Pittsburgh

Stay Pittsburgh
2.0 star property
8.0 out of 10, Very good, (216)
"Perfect place to stay for what I needed,everything is walkable if you don’t mind walking as I don’t mind it at all,great way to see the city "
Australia
Bradley
Stay Pittsburgh
Free WiFi
Melwood Suites Unit 107 Studio

Apartment in Oakland

Melwood Suites Unit 107 Studio
2.0 star property
9.6 out of 10, Exceptional, (41)
"Spotless, amazing stay"
United States
Carlos
The price is HK$924
HK$1,054 total
includes taxes & fees
28 Dec - 29 Dec
Melwood Suites Unit 107 Studio
Private kitchen
CozySuites - William

Aparthotel in Downtown Pittsburgh

CozySuites - William
2.0 star property
4.0 out of 10, (5)
"The apartment we rented had not been cleaned prior to our arrival. There were dirty linens, dirty handprints on doors and light switches, and when we stripped the bed linens prior to checkout there was a blood stain on the pillow. Yuck!"
United States
Don
The price is HK$490
HK$1,268 total
includes taxes & fees
21 Dec - 22 Dec
CozySuites - William
Interior
Abode Pittsburgh - Downtown Convention Center

Apartment in Downtown Pittsburgh

Abode Pittsburgh - Downtown Convention Center
3.5 star property
7.6 out of 10, Good, (87)
"Good location, clean place. Was affordable. Perfect for our guys weekend, with the 3 of us. "
United States
Michael
The price is HK$371
HK$1,213 total
includes taxes & fees
21 Dec - 22 Dec
Abode Pittsburgh - Downtown Convention Center
Private kitchen
CozySuites - Press House

Aparthotel in Downtown Pittsburgh

CozySuites - Press House
2.0 star property
3.6 out of 10, (5)
"Nice area in downtown Pittsburg PA. It was roomy. Furniture was cheap but we understand why. "
United States
Elliott
The price is HK$490
HK$1,224 total
includes taxes & fees
21 Dec - 22 Dec
CozySuites - Press House
2 bedrooms
2 Bedroom Downtown Apt Clean and Safe

Apartment in Downtown Pittsburgh

2 Bedroom Downtown Apt Clean and Safe
2.0 star property
10.0 out of 10, Exceptional, (1)
"I enjoyed the location very much. It was so easy to get to, everything was walking distance and the view was gorgeous. The rooms were tidy with comfortable furniture and smelled pleasant. I plan on trying to stay here anytime i am in the city. "
United States
Michael
The price is HK$854
HK$1,213 total
includes taxes & fees
21 Dec - 22 Dec
2 Bedroom Downtown Apt Clean and Safe
TV, fireplace
Stylish 4Bdr Loft Home, North Shore, City Skyline

Holiday Home in North Side

Stylish 4Bdr Loft Home, North Shore, City Skyline
9.6 out of 10, Exceptional, (42)
"Nice, updated, clean house that is walking distance to the north shore including PNC park, Steelers stadium and many other activities on that area. "
United States
Joshua M.
The price is HK$903
HK$1,223 total
includes taxes & fees
21 Dec - 22 Dec
Stylish 4Bdr Loft Home, North Shore, City Skyline
2 bedrooms
2 Bedroom 2 Bath Downtown Sleeps Six Walkable

Apartment in Downtown Pittsburgh

2 Bedroom 2 Bath Downtown Sleeps Six Walkable
2.0 star property
8.0 out of 10, Very good, (2)
"Basic amenities but excellent customer service. "
United States
Angelika
The price is HK$854
HK$1,213 total
includes taxes & fees
11 Jan - 12 Jan 2026
2 Bedroom 2 Bath Downtown Sleeps Six Walkable
2 bedrooms
6 Beds Downtown Apt Very Quick Walk Everywhere

Apartment in Downtown Pittsburgh

6 Beds Downtown Apt Very Quick Walk Everywhere
2.0 star property
10.0 out of 10, Exceptional, (2)
"We only stayed for one night went to the Steeler game ! Go Steelers ! Beat the Bengals by the way ! lol the location was great close to stadium. We walked afterwards. There was a couple of good bars in the neighborhood to watch the rest of the games and all it is a perfect spot specially if you're in for a game, I would highly recommend it to any of my friends or family "
United States
John
The price is HK$953
HK$1,326 total
includes taxes & fees
11 Jan - 12 Jan 2026
6 Beds Downtown Apt Very Quick Walk Everywhere
2 bedrooms
2 Bedroom 2 Bathroom The Heart of Pittsburgh

Apartment in Downtown Pittsburgh

2 Bedroom 2 Bathroom The Heart of Pittsburgh
2.0 star property
The price is HK$836
HK$1,193 total
includes taxes & fees
21 Dec - 22 Dec
2 Bedroom 2 Bathroom The Heart of Pittsburgh
1 bedroom
Cute Downtown APT Quick Safe Walk to PPG Arena

Apartment in Downtown Pittsburgh

Cute Downtown APT Quick Safe Walk to PPG Arena
2.0 star property
The price is HK$764
HK$1,111 total
includes taxes & fees
21 Dec - 22 Dec
Cute Downtown APT Quick Safe Walk to PPG Arena
1 bedroom
City Views Downtown Apt Walk Everywhere

Apartment in Downtown Pittsburgh

City Views Downtown Apt Walk Everywhere
2.0 star property
The price is HK$782
HK$1,131 total
includes taxes & fees
21 Dec - 22 Dec
City Views Downtown Apt Walk Everywhere
Private kitchen
CozySuites at Lawrenceville

Apartment in Lawrenceville

CozySuites at Lawrenceville
3.5 star property
7.4 out of 10, Good, (3)
"Great hip location walking distance to good food and cute shops. Public bus stop right next to development. Large studio suite decorated hip and modern. Great view of skyline from windows. All dishes and cookware are there if you choose to cook. Neighborhood is really nice and feels safe overall."
United States
Taylor
The price is HK$537
HK$1,552 total
includes taxes & fees
21 Dec - 22 Dec
CozySuites at Lawrenceville
Front of property
424-Apt. 403

Apartment in Oakland

424-Apt. 403
3.5 star property
9.6 out of 10, Exceptional, (33)
"The host is wonderful. "
United States
Chaz
The price is HK$840
HK$1,446 total
includes taxes & fees
20 Dec - 21 Dec
424-Apt. 403
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

Hilton Garden Inn Pittsburgh Downtown

Hilton Garden Inn Pittsburgh Downtown

10/10 Excellent
"Great location for downtown events"
KEVIN 2-night trip
Posted 17 hours ago
Hilton Garden Inn Pittsburgh Downtown

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