Holiday Homes in South Side

Start date: Check-in selected.
To Date
End date: Check-out

    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

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in South Side

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
2.0 star property
The price is AU$323
includes taxes & fees
21 Oct - 22 Oct
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
Pet-Friendly Southside Getaway - Sleeps 12
2.0 star property
The price is AU$881
includes taxes & fees
23 Oct - 24 Oct
Pet-Friendly Southside Getaway - Sleeps 12
Central 5BD Getaway - Spacious Home w/ BBQ
2.0 star property
10.0 out of 10, Exceptional, (9)
"Great property just a block away from restaurants and bars and a short ride away from the stadiums. Plenty of room for seven adults. Very clean with large, comfortable bedrooms and a fun outdoor patio. Phil and Dolly were gracious, responsive hosts. Highly recommend and would absolutely stay here again!"
United States
Anonymous traveller
The price is AU$696
includes taxes & fees
27 Oct - 28 Oct
Central 5BD Getaway - Spacious Home w/ BBQ
Hot Tub | King Bed | Games | Free Parking
10.0 out of 10, Exceptional, (3)
"Space was great. Bars and restaurants within walking distance. Would recommend! "
United States
Thomas Z.
The price is AU$555
includes taxes & fees
5 Nov - 6 Nov
Hot Tub | King Bed | Games | Free Parking
King Bed | Free Parking | Arcade | Fire Pit
10.0 out of 10, Exceptional, (20)
"Very comfortable"
United States
Deanna
The price is AU$574
includes taxes & fees
20 Oct - 21 Oct
King Bed | Free Parking | Arcade | Fire Pit
South Side Vibe! Pittsburgh's best location
9.4 out of 10, Exceptional, (8)
"It was an amazing place centerally located "
United States
Michelle A.
The price is AU$341
includes taxes & fees
20 Oct - 21 Oct
South Side Vibe! Pittsburgh's best location
City Skyline - Outside decks - Contemporary
10.0 out of 10, Exceptional, (3)
"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.
The price is AU$650
includes taxes & fees
23 Oct - 24 Oct
City Skyline - Outside decks - Contemporary
King Bed - BBQ & Hot Tub - Centrally Located
8.0 out of 10, Very good, (2)
"It was an excellent stay and a very accurate property description. "
United States
chad s.
The price is AU$537
includes taxes & fees
20 Oct - 21 Oct
King Bed - BBQ & Hot Tub - Centrally Located
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
7.8 out of 10, Good, (8)
"Tom was very communicative during the whole stay and had great recommendations! We loved the place, well situated on the South side for easy walking along Carson. Wonderful time in Pittsburgh! "
United States
Nathan H.
The price is AU$368
includes taxes & fees
20 Oct - 21 Oct
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!
10.0 out of 10, Exceptional, (14)
"Great stay! Very good location to get to the city and great restaurants. Amazing view! The host was very nice and great to work with. "
United States
Eric A.
The price is AU$1,107
includes taxes & fees
3 Nov - 4 Nov
Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
10.0 out of 10, Exceptional, (19)
"Beautiful property with all the amenities you could ever need for a weekend getaway "
United States
Amanda G.
The price is AU$964
includes taxes & fees
11 Nov - 12 Nov
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside
7.0 out of 10, Good, (4)
"Very well organized and clean. Host was quick to communicate and helpful."
United States
Noah S.
The price is AU$373
includes taxes & fees
20 Oct - 21 Oct
Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside
❤️Cozy Townhome on Carey with Private Deck Space ❤️
8.2 out of 10, Very good, (30)
"got a lil warm in the house the first night but over all a great place"
United States
chad M.
The price is AU$378
includes taxes & fees
21 Oct - 22 Oct
❤️Cozy Townhome on Carey with Private Deck Space ❤️
King Bed | Free Parking | BBQ | Fire pit | Arcade
9.6 out of 10, Exceptional, (64)
"Great place, modern, clean, exactly as advertised. Great communication, very responsive host and very proactive with helpful info. Highly recommend! "
United States
Ryan C.
The price is AU$597
includes taxes & fees
12 Nov - 13 Nov
King Bed | Free Parking | BBQ | Fire pit | Arcade
Pittsburgh Pennsylvania house
6.0 out of 10, (2)
"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 AU$422
includes taxes & fees
20 Oct - 21 Oct
Pittsburgh Pennsylvania house
CozySuites Modern 1BR in Downtown Pitts #14
2.0 star property
The price is AU$259
includes taxes & fees
20 Oct - 21 Oct
CozySuites Modern 1BR in Downtown Pitts #14
5211 Penn Ave - Bloomfield
2.0 star property
The price is AU$545
includes taxes & fees
20 Oct - 21 Oct
5211 Penn Ave - Bloomfield
Restful Nest near downtown
9.0 out of 10, Wonderful, (6)
"Stayed over after concert and avoided all the traffic. Convenient to Station Square parking and Gateway Clipper. Owner very responsive to messages and questions. Comfortable beds, clean and updated."
United States
Gregory S.
The price is AU$467
includes taxes & fees
21 Oct - 22 Oct
Restful Nest near downtown
183 Banner Way - Lawrenceville
10.0 out of 10, Exceptional, (10)
"Very nice place. Close to Butler street which has great restaurants & shops!"
United States
Heather z.
The price is AU$348
includes taxes & fees
20 Oct - 21 Oct
183 Banner Way - Lawrenceville
★ HostWise Stays ★ 4 Blocks From UPMC Children's
10.0 out of 10, Exceptional, (13)
"Great location and comfortable stay overall. Would recommend. Internet speed and reliability was excellent for remote work."
United States
Josh C.
The price is AU$295
includes taxes & fees
20 Oct - 21 Oct
★ HostWise Stays ★ 4 Blocks From UPMC Children's
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 Holiday Homes information

Number of reviews
Accommodation
Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia