South Side Holiday Rentals

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

Holiday Rentals in South Side

Pet-Friendly Southside Getaway - Sleeps 12
2.0 star property
The price is AU$763
includes taxes & fees
29 Oct - 30 Oct
Pet-Friendly Southside Getaway - Sleeps 12
Cozy&Modern 2Bdr Apt PIttsburgh
2.0 star property
10.0 out of 10, Exceptional, (8)
"Good location right of East Carson. Enjoyed our stay."
United States
Emma P.
The price is AU$220
includes taxes & fees
13 Nov - 14 Nov
Cozy&Modern 2Bdr Apt PIttsburgh
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$345
includes taxes & fees
29 Oct - 30 Oct
South Side Vibe! Pittsburgh's best location
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
Kasa South Side Pittsburgh
4.0 star property
8.2 out of 10, Very good, (101)
"Clean great views hotel "
United States
Shomario
The price is AU$270
includes taxes & fees
3 Nov - 4 Nov
Kasa South Side Pittsburgh
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
2.0 star property
The price is AU$322
includes taxes & fees
23 Oct - 24 Oct
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
2615 Jane Down - Southside
2.0 star property
The price is AU$295
includes taxes & fees
28 Oct - 29 Oct
2615 Jane Down - Southside
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$545
includes taxes & fees
5 Nov - 6 Nov
Hot Tub | King Bed | Games | Free Parking
⁂ Cozy Nook off Carson - Free Parking & Private Entry ⁂
9.6 out of 10, Exceptional, (11)
"Tom was thorough, polite and extremely quick to answer any questions I had. You can’t beat the location with so many great restaurants and bars within walking distance. Definitely recommend! "
United States
Brenna O.
The price is AU$321
includes taxes & fees
28 Oct - 29 Oct
⁂ Cozy Nook off Carson - Free Parking & Private Entry ⁂
*Historic Gem* Heart of Southside-Sleeps 10
9.4 out of 10, Exceptional, (22)
"Property was perfect for a quick weekend visit to attend a concert at PPG arena. "
United States
Corrie W.
The price is AU$441
includes taxes & fees
23 Oct - 24 Oct
*Historic Gem* Heart of Southside-Sleeps 10
King Bed | Free Parking | Arcade | Fire Pit
10.0 out of 10, Exceptional, (20)
"Very comfortable"
United States
Deanna
The price is AU$573
includes taxes & fees
28 Oct - 29 Oct
King Bed | Free Parking | Arcade | Fire Pit
City Skyline - Outside decks - Contemporary
10.0 out of 10, Exceptional, (4)
"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
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$518
includes taxes & fees
29 Oct - 30 Oct
King Bed - BBQ & Hot Tub - Centrally Located
Carey Way Quarters – Stylish 3-Bedroom Loft!
9.4 out of 10, Exceptional, (3)
"Good location and place for my quick stay in Pittsburgh."
United States
John M.
Carey Way Quarters – Stylish 3-Bedroom Loft!
❤️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$381
includes taxes & fees
23 Oct - 24 Oct
❤️Cozy Townhome on Carey with Private Deck Space ❤️
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$372
includes taxes & fees
3 Nov - 4 Nov
Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside
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$381
includes taxes & fees
27 Oct - 28 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$1,108
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$976
includes taxes & fees
11 Nov - 12 Nov
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
Industrial Chic Studio-Modern Comfort in the Burgh
10.0 out of 10, Exceptional, (4)
"Great place to stay. Easy access to bridges which then led us to Pitt to visit. Owner was very responsive to our questions. We'd stay here again!"
United States
Rich D.
The price is AU$589
includes taxes & fees
14 Nov - 15 Nov
Industrial Chic Studio-Modern Comfort in the Burgh
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

Everything you need to know about South Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Side holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

South Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Side holiday rentals we have selected for you start as low as AU$194 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on South Side rentals

At Expedia, we put the best South Side holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top South Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Side holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.