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 bedroom with a bed, bedside tables, a mirror, and a door.

1. Spacious 2BR South Side Retreat | Free Parking | Fast WiFi

South Side Slopes

HK$1,860 total

includes taxes & fees

1 Oct - 2 Oct

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

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

South Side Flats

Butch K.

HK$1,750 total

includes taxes & fees

5 Oct - 6 Oct

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

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

South Side Flats

Manuel M.

HK$2,130 total

includes taxes & fees

29 Sept - 30 Sept

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

South Side Flats

Heather B.

HK$2,186 total

includes taxes & fees

6 Oct - 7 Oct

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

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

Allentown

John

HK$2,135 total

includes taxes & fees

29 Sept - 30 Sept

An outdoor deck with a fire feature, seating, and a view of the city at night.

6. City Skyline - Outside decks - Contemporary

South Side Slopes

Glen C.

HK$3,008 total

includes taxes & fees

30 Sept - 1 Oct

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

7. 3-bedroom house in Southside Flats neighborhood of Pittsburgh.

South Side Flats

Kyle S.

HK$1,855 total

includes taxes & fees

30 Sept - 1 Oct

A living room with a sectional sofa, a coffee table, a patterned rug, and a wall-mounted airplane artwork.

8. Cozy South Side Retreat | Free Parking | Fast WiFi

South Side Slopes

A kitchen with wooden cabinets, stainless steel appliances, and a built-in oven.

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

South Side Flats

Mark W.

HK$3,204 total

includes taxes & fees

6 Oct - 7 Oct

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

10. Pittsburgh Pennsylvania house

South Side Flats

Adrian C.

HK$2,127 total

includes taxes & fees

20 Oct - 21 Oct

A row of brick townhouses with front porches, a small garden, and a visible mailbox.

11. Central 5BD Getaway - Spacious Home w/ BBQ

South Side Flats

Sean O.

HK$3,711 total

includes taxes & fees

29 Sept - 30 Sept

A wooden deck with potted plants and a hanging fern.

12. Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

South Side Flats

Kevin M.

HK$4,531 total

includes taxes & fees

29 Sept - 30 Sept

A backyard with a fire pit, a white chair, a colorful wall, and a wooden fence.

13. Pittsburgh House with Hot Tub, Patio & Free Parking!

South Side Flats

Sara P.

A modern kitchen with white cabinets, stainless steel appliances, and a central island with a basket of decorative items.

14. Clean and comfortable 3BR home in the South Side neighborhood

South Side Slopes

Amanda R.

A backyard with a grill, hot tub, and patio furniture.

15. Southside Gem w Hot Tub and Dedicated Parking

South Side Slopes

HK$10,232 total

includes taxes & fees

8 Oct - 9 Oct

A cityscape with a river, a bridge, and a pedestrian walkway.

16. Urban Retreat with Garage on Mt. Washington

Mount Washington

David M.

HK$1,599 total

includes taxes & fees

26 Oct - 27 Oct

A living room with a fireplace, two armchairs, a sofa, and a patterned rug.

17. Relax & Feel At Home During Your Pittsburgh Stay

Carrick

Kay K.

HK$1,815 total

includes taxes & fees

1 Oct - 2 Oct

A cozy living room with a brick fireplace, a wooden dining table, and a staircase.

18. 1209 Ocala St Pittsburgh

North Side

"The house was very cool place - lots of interesting touches, very clean and had everything we needed.The host was so easy to communicate with and provided very clear instructions, which was very important regarding the parking.The location was also perfect - easy walking distance to PNC Park, the River Trail and other landmarks.We would definitely stay here again and are already looking forward to our next visit!!"

Mary B.

HK$2,022 total

includes taxes & fees

29 Sept - 30 Sept

A modern kitchen with white cabinetry, granite countertops, stainless steel appliances, and a unique spiral pendant light.

19. Stylish & Central 3BD Home Pittsburgh/North Side with Free Street Parking

North Side

Shawn H.

HK$957 total

includes taxes & fees

1 Oct - 2 Oct

A modern kitchen with a white brick wall, a flat-screen TV mounted above a wooden shelf, and a bar area with stools.

20. 307 37th St · Lawrenceville Row House - Walk to Everything!

Lawrenceville

Cassi D.

HK$1,395 total

includes taxes & fees

5 Oct - 6 Oct

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Top South Side Hotel Reviews

Springhill Suites by Marriott Pittsburgh North Shore

10/10 Excellent

"The hotel was clean, comfortable and had a perfect location for a Steelers game and enjoying the North Shore area!"

Wyndham Grand Pittsburgh Downtown

8/10 Good

"Beautiful hotel and a great location. It was expensive. Breakfast was not included. Staff was extremely helpful when the person next to us flooded their room, the hallway, & our room. Moved us to another room that was pretty but impractical. No room for anything in the shower. Very little counter space & the room was much smaller & no room for suitcases. I wish we could have stayed in our first room."

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