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Our top choices for South Side vacation homes

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

Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
2.0 star property
South Side Slopes
The price is AED 385
AED 1,127 total
includes taxes & fees
11 Jan - 12 January 2026
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views

Hot Tub | King Bed | Games | Free Parking

Hot Tub | King Bed | Games | Free Parking
South Side Flats
10.0 out of 10, Exceptional, (4)
"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 AED 514
AED 1,385 total
includes taxes & fees
17 Dec - 18 Dec
Hot Tub | King Bed | Games | Free Parking

King Bed | Free Parking | Arcade | Fire Pit

King Bed | Free Parking | Arcade | Fire Pit
South Side Flats
10.0 out of 10, Exceptional, (23)
"Very comfortable"
United States
Deanna
The price is AED 477
AED 1,339 total
includes taxes & fees
6 Jan - 7 January 2026
King Bed | Free Parking | Arcade | Fire Pit

City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
10.0 out of 10, Exceptional, (4)
"our stay was great, the space was everything that was advertised and more. We especially loved the views of Pittsburgh constantly surrounding us. To have the four different porches was astounding. It suited us to hold us for the funeral of my brother which was why we were in Pittsburgh. I would highly recommend this spot for a big group needing a wonderful convenient spot in Pittsburgh. "
United States
Sandy S.
The price is AED 509
AED 1,566 total
includes taxes & fees
17 Dec - 18 Dec
City Skyline - Outside decks - Contemporary

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)
"It was an excellent stay and a very accurate property description. "
United States
chad s.
The price is AED 398
AED 1,299 total
includes taxes & fees
17 Dec - 18 Dec
King Bed - BBQ & Hot Tub - Centrally Located

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

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
2.0 star property
South Side Flats
The price is AED 381
AED 827 total
includes taxes & fees
4 Jan - 5 January 2026
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

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

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
South Side Flats
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 AED 184
AED 915 total
includes taxes & fees
22 Dec - 23 Dec
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

Central 5BD Getaway - Spacious Home w/ BBQ

Central 5BD Getaway - Spacious Home w/ BBQ
2.0 star property
South Side Flats
10.0 out of 10, Exceptional, (9)
"Great Location and great time. Host was EXTREMELY responsive it was nice "
United States
John L.
The price is AED 1,011
AED 2,177 total
includes taxes & fees
12 Dec - 13 Dec
Central 5BD Getaway - Spacious Home w/ BBQ

❤️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, (32)
"This house worked excellent for our family to stay for the weekend for college graduation. Perfect location to get around and see South Side."
United States
Michael P.
The price is AED 184
AED 903 total
includes taxes & fees
16 Dec - 17 Dec
❤️Cozy Townhome on Carey with Private Deck Space ❤️

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, (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 AED 1,175
AED 2,468 total
includes taxes & fees
16 Dec - 17 Dec
Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!

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)
"Fantastic property. Intriguing history. Great location."
United States
Kevin M.
The price is AED 1,234
AED 2,279 total
includes taxes & fees
17 Dec - 18 Dec
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

King Bed | Free Parking | BBQ | Fire pit | Arcade

King Bed | Free Parking | BBQ | Fire pit | Arcade
South Side Flats
9.8 out of 10, Exceptional, (66)
"Everything was perfect and we hope to come back again soon. Rank One is ranked #1 in my book. Thanks for a great stay!"
United States
Joseph M.
The price is AED 371
AED 1,246 total
includes taxes & fees
7 Jan - 8 January 2026
King Bed | Free Parking | BBQ | Fire pit | Arcade

Pittsburgh Pennsylvania house

Pittsburgh Pennsylvania house
South Side Flats
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 AED 452
AED 1,037 total
includes taxes & fees
17 Dec - 18 Dec
Pittsburgh Pennsylvania house

The Light Room

The Light Room
McKeesport
9.6 out of 10, Exceptional, (4)
"The house has a very peaceful atmosphere."
United States
Susan G.
The price is AED 331
AED 623 total
includes taxes & fees
17 Dec - 18 Dec
The Light Room

The Upper Room

The Upper Room
McKeesport
9.4 out of 10, Exceptional, (6)
"Great place and an awesome host!"
United States
John B.
The price is AED 349
AED 644 total
includes taxes & fees
12 Dec - 13 Dec
The Upper Room

Spacious 4-bedroom house in beautiful Pittsburgh

Spacious 4-bedroom house in beautiful Pittsburgh
2.0 star property
Pittsburgh
The price is AED 294
AED 1,234 total
includes taxes & fees
22 Dec - 23 Dec
Spacious 4-bedroom house in beautiful Pittsburgh

★ HostWise Stays ★ 4 Blocks From UPMC Children's

★ HostWise Stays ★ 4 Blocks From UPMC Children's
Lawrenceville
10.0 out of 10, Exceptional, (14)
"Great location and communication from host! The home was clean, comfortable, and exactly as described. We loved and appreciated the kitchen amenities! We very much enjoyed our stay. We would absolutely stay here again and highly recommend this rental. "
United States
Heather S.
The price is AED 276
AED 724 total
includes taxes & fees
17 Dec - 18 Dec
★ HostWise Stays ★ 4 Blocks From UPMC Children's

Craftsman Charmer | Easy Access to City & Airport

Craftsman Charmer | Easy Access to City & Airport
Crafton Heights
9.6 out of 10, Exceptional, (16)
"We enjoyed our visit to Pittsburgh, we would definitely stay here again. "
United States
Jamie B.
The price is AED 253
AED 661 total
includes taxes & fees
19 Dec - 20 Dec
Craftsman Charmer | Easy Access to City & Airport

Restful Nest near downtown

Restful Nest near downtown
Brookline
9.0 out of 10, Wonderful, (7)
"This house was perfect for our weekend stay for the Steelers game. It is just a few miles drive to the stadium. There is a large variety of restaurants close by. The house was clean and comfortable and well stocked with whatever you may need for your stay."
United States
Mark D.
The price is AED 413
AED 1,091 total
includes taxes & fees
16 Dec - 17 Dec
Restful Nest near downtown

Stylish House near Frick Park

Stylish House near Frick Park
Squirrel Hill South
9.8 out of 10, Exceptional, (9)
"Stayed for the US Open. Check in was easy and property was clean and comfortable. "
United States
Joshua H.
The price is AED 309
AED 726 total
includes taxes & fees
18 Dec - 19 Dec
Stylish House near Frick Park
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