South Side Vacation Homes

A park with autumn trees, a bridge, and a building labeled UPMC in the background.

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Our top choices for South Side holiday homes

A modern living room with a sectional sofa, a dark coffee table, and a world map on the wall.

1. Iron City of South Side Flats Charming 2-bedroom Unit

South Side Flats

Manuel M.

HK$2,206 total

includes taxes & fees

21 Oct - 22 Oct

2. Steel City of South Side Flats Charming 2-Bedroom Unit

South Side Flats

Heather B.

HK$2,142 total

includes taxes & fees

20 Oct - 21 Oct

A bedroom with a bed, two pillows, a wall-mounted sign, and a window with blinds.

3. Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi

South Side Slopes

HK$1,598 total

includes taxes & fees

8 Nov - 9 Nov

A dining area with a round table, white chairs, a hanging light fixture, a radiator, and a colorful cityscape painting on the wall.

4. 3-bedroom house in Southside Flats neighborhood of Pittsburgh.

South Side Flats

Kyle S.

HK$1,802 total

includes taxes & fees

19 Oct - 20 Oct

A living room with a green sofa, a glass coffee table, a TV mounted on the wall, and a sliding barn door.

5. Cozy Centralized 3bd 2bath House w/ Free Parking

South Side Flats

Mark W.

HK$4,689 total

includes taxes & fees

20 Oct - 21 Oct

A living room with a fireplace, a television, and a dining area with a table and chairs.

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

South Side Flats

Butch K.

HK$1,609 total

includes taxes & fees

27 Oct - 28 Oct

An outdoor dining area with a wooden table and black chairs, surrounded by string lights and a white pergola.

7. Pittsburgh Pennsylvania house

South Side Flats

Adrian C.

HK$2,064 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with white cabinets, a stainless steel dishwasher, a microwave, and a black countertop.

8. Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Allentown

John

HK$2,257 total

includes taxes & fees

25 Oct - 26 Oct

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Top South Side Hotel Reviews

Cambria Hotel Pittsburgh - Downtown

10/10 Excellent

"The best water pressure I have ever experienced! It was quite, clean, and staff was friendly"

Placemakr Downtown Pittsburgh at The Pennsylvanian

10/10 Excellent

"This building is absolutely beautiful. Our room was a one bedroom apartment style, very clean and modern. It was always quiet and could barely hear the outside traffic. They have an amazing coffee machine in the lobby with multiple options from espresso, hot chocolate, etc. The hotel staff went above and beyond for us. They even lent us an umbrella on a rainy day. I've stayed at a lot of places including vrbo and this was the best place I've ever stayed at."

Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent

"You’ll stay in a historic renovated Federal Reserve Bank, complete with huge vaults in the cellar. Wonderful spaces to enjoy free breakfast, hot appetizers and a drink each day. The 8th floor has a lovely pool, workout space and outdoor patio with city views. Quiet, solid materials, comfy beds and a. hard working staff make this a hotel to come back to."

Pittsburgh Marriott City Center

10/10 Excellent

"The location was perfect as we arrived by car and it’s close to the highway. But we could also walk to downtown theater district. The room was not only spacious but enormous. The staff were fantastic. Dee at the front desk was particularly helpful and made us feel welcome. She went above and beyond. Brian, the concierge loaned us his personal umbrella when we had to go out in the rain. My only caveat is that the on-site restaurant is not good. The service was terrible and the food was even worse. But the ambience is good. I would highly recommend this property."

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