Holiday Rentals in South Side

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Holiday Rentals in South Side

Our top choices for South Side holiday rentals

Kasa South Side Pittsburgh

4.0 star property
8.2 out of 10, Very good, (89)
"Surprised at the room cleanliness. This is our 4th time staying at this property. And the no parking was a little disappointing."
Kasa South Side Pittsburgh

Walkable Studio in the Heart of Pittsburgh!

3.0 star property
Walkable Studio in the Heart of Pittsburgh!

Cozy&Modern 2Bdr Apt PIttsburgh

2.0 star property
10.0 out of 10, Exceptional, (4)
"Good location right of East Carson. Enjoyed our stay."
The price is €119
includes taxes & fees
24 Aug - 25 Aug
Cozy&Modern 2Bdr Apt PIttsburgh

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (26)
"got a lil warm in the house the first night but over all a great place"
The price is €216
includes taxes & fees
25 Aug - 26 Aug
❤️Cozy Townhome on Carey with Private Deck Space ❤️

Charming 2-bedroom apartment In Pittsburgh, Southside!

4.0 out of 10, (3)
"The apartment itself is lovely. There is one reason I would not stay here is there is a horrible gut wrenching smell in hallway and the entire apartment. At first we thought someone was cooking with very intense spices until we got inside apartment and it smelled the same with same intensity. This smell did not go away for the two days we were there. Only relief we got was when opening windows. Luckily had air freshener in the car. There were plug-ins but only one had deodorizer in it. The host...
The price is €291
includes taxes & fees
24 Aug - 25 Aug
Charming 2-bedroom apartment In Pittsburgh, Southside!

*Historic Gem* Heart of Southside-Sleeps 10

9.6 out of 10, Exceptional, (18)
"Property was perfect for a quick weekend visit to attend a concert at PPG arena. "
The price is €251
includes taxes & fees
24 Aug - 25 Aug
*Historic Gem* Heart of Southside-Sleeps 10

Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside

6.0 out of 10, (3)
"Excellent communication with owner. Fast, friendly and courteous. Located about 450 meter walk up a large hill from Penn Avenue (bus 88) which is about 35 minutes to downtown. Apartment showing its age but fair value for cost. "
The price is €182
includes taxes & fees
31 Aug - 1 Sept
Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside

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

9.4 out of 10, Exceptional, (3)
"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! "
The price is €217
includes taxes & fees
25 Aug - 26 Aug
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

Stay Pittsburgh

2.0 star property
7.8 out of 10, Good, (169)
"Clean and good location "
The price is €129
includes taxes & fees
27 Aug - 28 Aug
Stay Pittsburgh

Placemakr Downtown Pittsburgh at The Pennsylvanian

4.0 star property
7.6 out of 10, Good, (16)
"The unit we stayed in was impeccable. Very beautifully decorated and comfy and homelike. Would definitely stay there again. "
The price is €145
includes taxes & fees
4 Sept - 5 Sept
Placemakr Downtown Pittsburgh at The Pennsylvanian

Melwood Suites Unit 107 Studio

2.0 star property
9.6 out of 10, Exceptional, (30)
"We loved how modern and quiet the place was."
The price is €113
includes taxes & fees
1 Sept - 2 Sept
Melwood Suites Unit 107 Studio

Abode Pittsburgh - Downtown Convention Center

3.5 star property
7.6 out of 10, Good, (82)
"Location nice"
The price is €157
includes taxes & fees
25 Aug - 26 Aug
Abode Pittsburgh - Downtown Convention Center

Stylish & Central 3BD Home Pittsburgh/North Side

10.0 out of 10, Exceptional, (11)
"Super clean and comfortable. Centrally located. Great for family. Everyone enjoyed their stay."
The price is €126
includes taxes & fees
24 Aug - 25 Aug
Stylish & Central 3BD Home Pittsburgh/North Side

*New* Loft 3 min to Local hospitals Sleeps 4

2.0 star property
10.0 out of 10, Exceptional, (8)
"Very cool space. Immediate area is sparse. But a quick walk or drive and tons to see and do. "
The price is €138
includes taxes & fees
25 Aug - 26 Aug
*New* Loft 3 min to Local hospitals Sleeps 4

Downtown Estate! Can sleep up to 24!

10.0 out of 10, Exceptional, (1)
"Was in town for an unfortunate situation due to a family member needing an emergency surgery and was a little worried about booking a property with no reviews, but after speaking with the owner, I was put at ease and let me tell you this property is not only in a great location, but also such a beautiful property and the house even provided breakfast, pastries, and snacks as well as drinks so definitely already looking into booking another trip out to Pittsburgh just to stay here! "
Downtown Estate! Can sleep up to 24!

Spacious 3-bedroom house in scenic Mt. Washington near Grandview's city view

2.0 star property
9.8 out of 10, Exceptional, (17)
"House was clean and exactly as described in the listing, had a wonderful time in Mt Washington!"
Spacious 3-bedroom house in scenic Mt. Washington near Grandview's city view

CozySuites - William

2.0 star property
3.0 out of 10, (4)
"The apartment we rented had not been cleaned prior to our arrival. There were dirty linens, dirty handprints on doors and light switches, and when we stripped the bed linens prior to checkout there was a blood stain on the pillow. Yuck!"
The price is €145
includes taxes & fees
9 Sept - 10 Sept
CozySuites - William

Stylish 4Bdr Loft Home, North Shore, City Skyline

9.8 out of 10, Exceptional, (30)
"Would definitely stay again. No problems whatsoever Recommend"
The price is €146
includes taxes & fees
17 Sept - 18 Sept
Stylish 4Bdr Loft Home, North Shore, City Skyline

CozySuites - Press House

2.0 star property
4.0 out of 10, (2)
"Nice area in downtown Pittsburg PA. It was roomy. Furniture was cheap but we understand why. "
The price is €155
includes taxes & fees
24 Aug - 25 Aug
CozySuites - Press House

Historic 2 Bedroom Loft on Market Square - Private Terrace + Free Fitness Center

9.8 out of 10, Exceptional, (15)
"The space is fantastic! The owner was so very helpful and amazing. All questions answered very quickly. Love the area and would definitely rent again!!! "
Historic 2 Bedroom Loft on Market Square - Private Terrace + Free Fitness Center
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