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

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 ¥13,707
¥32,902 total
includes taxes & fees
May 11 - May 12
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

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 ¥15,668
¥45,553 total
includes taxes & fees
May 20 - May 21
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

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 ¥37,760
¥74,447 total
includes taxes & fees
May 26 - May 27
King Bed | Garage Door Patio | Free Parking

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 ¥11,297
¥35,857 total
includes taxes & fees
May 10 - May 11
South Side Vibe! Pittsburgh's best location

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 ¥16,098
¥43,959 total
includes taxes & fees
May 10 - May 11
Iron City of South Side Flats Charming 2-bedroom Unit

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 ¥16,098
¥43,959 total
includes taxes & fees
May 10 - May 11
Steel 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 ¥50,208
¥104,762 total
includes taxes & fees
May 10 - May 11
Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!

Cozy Centralized 3bd 2bath House w/ Free Parking

Cozy Centralized 3bd 2bath House w/ Free Parking
South Side Flats
The price is ¥18,467
¥68,462 total
includes taxes & fees
May 20 - May 21
Cozy Centralized 3bd 2bath House w/ Free Parking

Sarah St retreat - Modern 5 bed 3.5 ba - South Side Flats - Walk to Carson St

Sarah St retreat - Modern 5 bed 3.5 ba - South Side Flats - Walk to Carson St
South Side Flats
10.0 out of 10, Exceptional, (6 reviews)
The price is ¥21,152
¥72,349 total
includes taxes & fees
May 17 - May 18
Sarah St retreat - Modern 5 bed 3.5 ba - South Side Flats - Walk to Carson St

City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
9.6 out of 10, Exceptional, (5 reviews)
"We appreciated the way most everything was as shown in photos and loved the 4 furnished decks. The owner quickly responded to our needs and questions. Nice to have parking not on street."
United States
Deborah C.
City Skyline - Outside decks - Contemporary

Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views

Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
South Side Slopes
10.0 out of 10, Exceptional, (2 reviews)
"Great stay! Rooms were comfortable and very clean. "
United States
Anonymous traveler
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views

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 ¥37,603
¥48,232 total
includes taxes & fees
May 13 - May 14
Cozy Cabin in the City All the comforts of home, parking, pets allowed. Sleeps 8

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 ¥33,261
¥76,708 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 ¥55,841
¥86,994 total
includes taxes & fees
May 22 - May 23
Pittsburgh Pennsylvania house

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 ¥52,644
¥97,704 total
includes taxes & fees
May 26 - May 27
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 ¥16,451
¥31,038 total
includes taxes & fees
May 13 - May 14
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 ¥16,451
¥31,038 total
includes taxes & fees
May 12 - May 13
The Light Room

Lovely Strip District loft with free parking

Lovely Strip District loft with free parking
Strip District
10.0 out of 10, Exceptional, (33 reviews)
"Great location and really nice property."
United States
Tracy H.
The price is ¥19,629
¥32,102 total
includes taxes & fees
May 17 - May 18
Lovely Strip District loft with free parking

Beautiful 3BR Home with Cozy Front & Back Porches!

Beautiful 3BR Home with Cozy Front & Back Porches!
Munhall
9.4 out of 10, Exceptional, (28 reviews)
"Beautiful house and very cozy feeling, Jenna kept in touch to make sure we had everything we needed. "
United States
Bobbi C.
The price is ¥18,357
¥39,749 total
includes taxes & fees
May 15 - May 16
Beautiful 3BR Home with Cozy Front & Back Porches!

Strip District Studio-Free Parking-Natural Light

Strip District Studio-Free Parking-Natural Light
Strip District
9.2 out of 10, Wonderful, (27 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 ¥16,921
¥28,891 total
includes taxes & fees
May 13 - May 14
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
180
Accommodation
714 Vacation Homes
Lowest Price
¥28,891
Highest Price
¥104,762

Explore a world of travel with Expedia