Search Vacation Homes in South Side

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for South Side vacation homes

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
South Side Flats
8.0 out of 10, Very Good, (11 reviews)
"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 ¥6,058
¥37,521 total
includes taxes & fees
Apr 30 - May 1
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
South Side Flats
10.0 out of 10, Exceptional, (1 review)
"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 ¥13,940
¥33,120 total
includes taxes & fees
May 6 - May 7
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

King Bed | Garage Door Patio | Free Parking

King Bed | Garage Door Patio | Free Parking
South Side Flats
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful, spacious home, perfect for hosting our Friendsgiving! Love the backyard space. "
United States
Lia L.
The price is ¥33,510
¥77,101 total
includes taxes & fees
May 26 - May 27
King Bed | Garage Door Patio | Free Parking

❤️Cozy Townhome on Carey with Private Deck Space ❤️

❤️Cozy Townhome on Carey with Private Deck Space ❤️
South Side Flats
8.2 out of 10, Very Good, (37 reviews)
"Great location near the local nightlife"
United States
Andrew M.
The price is ¥6,058
¥36,668 total
includes taxes & fees
Apr 30 - May 1
❤️Cozy Townhome on Carey with Private Deck Space ❤️

South Side Vibe! Pittsburgh's best location

South Side Vibe! Pittsburgh's best location
South Side Flats
9.6 out of 10, Exceptional, (12 reviews)
"Nice place"
United States
Andres M.
The price is ¥12,925
¥37,933 total
includes taxes & fees
May 4 - May 5
South Side Vibe! Pittsburgh's best location

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Allentown
The price is ¥15,941
¥46,347 total
includes taxes & fees
May 20 - May 21
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Cozy Centralized 3bd 2bath House w/ Free Parking

Cozy Centralized 3bd 2bath House w/ Free Parking
South Side Flats
The price is ¥14,534
¥64,272 total
includes taxes & fees
May 6 - May 7
Cozy Centralized 3bd 2bath House w/ Free Parking

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, (1 review)
"Minus parking great stay will be back "
United States
Yolanda D.
The price is ¥18,095
¥46,840 total
includes taxes & fees
May 12 - May 13
Iron City of South Side Flats Charming 2-bedroom Unit

Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!

Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!
South Side Slopes
10.0 out of 10, Exceptional, (16 reviews)
"My family and I had an excellent stay. The home was very nice, the host was very helpful, and the view was incredible! If you are looking for a rental that is close to everything but gives you the opportunity to get away from the busy city for some relaxation, this is your place."
United States
Jason M.
The price is ¥51,062
¥106,544 total
includes taxes & fees
Apr 30 - May 1
Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!

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, (1 review)
"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 ¥18,095
¥46,840 total
includes taxes & fees
May 12 - May 13
Steel City of South Side Flats Charming 2-Bedroom Unit

NFL Draft House - Sleeps 12+ - South Side - Walk to Carson St

NFL Draft House - Sleeps 12+ - South Side - Walk to Carson St
South Side Flats
10.0 out of 10, Exceptional, (6 reviews)
The price is ¥19,388
¥71,571 total
includes taxes & fees
May 4 - May 5
NFL Draft House - Sleeps 12+ - South Side - Walk to Carson St

Cozy Cabin in the City All the comforts of home, parking, pets allowed. Sleeps 8

Cozy Cabin in the City All the comforts of home, parking, pets allowed. Sleeps 8
South Side Flats
The price is ¥38,297
¥49,634 total
includes taxes & fees
May 4 - May 5
Cozy Cabin in the City All the comforts of home, parking, pets allowed. Sleeps 8

Hot Tub | King Bed | Games | Free Parking

Hot Tub | King Bed | Games | Free Parking
South Side Flats
10.0 out of 10, Exceptional, (6 reviews)
"Perfect vibes for a small girls trip. Great location. Such a fun place, thanks for the small details!"
United States
Sara P.
The price is ¥113,181
¥180,509 total
includes taxes & fees
Apr 30 - May 1
Hot Tub | King Bed | Games | Free Parking

King Bed - BBQ & Hot Tub - Centrally Located

King Bed - BBQ & Hot Tub - Centrally Located
South Side Flats
8.0 out of 10, Very Good, (2 reviews)
"It was an excellent stay and a very accurate property description. "
United States
chad s.
The price is ¥39,698
¥85,731 total
includes taxes & fees
May 12 - May 13
King Bed - BBQ & Hot Tub - Centrally Located

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 ¥29,840
¥57,128 total
includes taxes & fees
Apr 30 - May 1
Pittsburgh Pennsylvania house

Pittsburgh Gem - 5BR - Downtown Deck View

Pittsburgh Gem - 5BR - Downtown Deck View
South Side Flats
10.0 out of 10, Exceptional, (4 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.
The price is ¥56,169
¥111,969 total
includes taxes & fees
May 1 - May 2
Pittsburgh Gem - 5BR - Downtown Deck View

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, (20 reviews)
"Fantastic property. Intriguing history. Great location."
United States
Kevin M.
The price is ¥53,616
¥100,360 total
includes taxes & fees
May 20 - May 21
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

The Upper Room

The Upper Room
McKeesport
9.6 out of 10, Exceptional, (7 reviews)
"Great place and an awesome host!"
United States
John B.
The price is ¥16,755
¥31,952 total
includes taxes & fees
May 11 - May 12
The Upper Room

The Light Room

The Light Room
McKeesport
9.6 out of 10, Exceptional, (9 reviews)
"Everything was great!!"
United States
Jason B.
The price is ¥16,755
¥31,952 total
includes taxes & fees
May 11 - May 12
The Light Room

Strip District Studio-Free Parking-Natural Light

Strip District Studio-Free Parking-Natural Light
Strip District
9.4 out of 10, Exceptional, (26 reviews)
"Great little place for my husband and I to stay during our quick trip. Comfy Murphy bed, nice rain shower with good water pressure. Although we only got takeout, full kitchen available with everything you would need. Would stay again! "
United States
Lauren O.
The price is ¥22,921
¥36,307 total
includes taxes & fees
May 12 - May 13
Strip District Studio-Free Parking-Natural Light
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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Side Hotel Reviews

Find out more about South Side

South Side Vacation Homes information

Number of reviews
131
Accommodation
714 Vacation Homes
Lowest Price
¥31,952
Highest Price
¥180,509

Explore a world of travel with Expedia