South Side, PA Vacation Homes from AED 686

South Side Vacation Homes
Pittsburgh
Pennsylvania
United States of America
Expedia.ae

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 vacation homes

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

A neatly made bed with a white duvet and a single yellow pillow, a cityscape artwork above it, and a desk with a chair to the right.

A framed historical map of Pittsburgh on a wall, a white door with a black handle, and a light switch.

A building with a grey brick exterior, a white door with a diamond pattern, and a black awning above the door.

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

Iron City of South Side Flats Charming 2-bedroom Unit

South Side Flats

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Excellent property. Very convenient having on-site parking. Super clean, cozy, comfortable and well located. Will stay again this upcoming weekend!"

Manuel M.

Iron City of South Side Flats Charming 2-bedroom Unit

A living room with a gray sectional sofa, a coffee table, and a ceiling fan. There are shelves with decorative items and a framed picture on the wall.

A residential building with a grey exterior, a metal staircase leading to a door, and a garage door.

A bedroom with a bed, a ceiling fan, an air conditioner, a desk with a chair, a plant, and a wooden floor.

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

Steel City of South Side Flats Charming 2-Bedroom Unit

South Side Flats

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Great location, appreciated off-street gated parking at residence. Unit is updated and clean with lots of modern amenities. Had a great visit, would definitely stay here again."

Heather B.

The price is AED 592

AED 592

AED 1,305 total

includes taxes & fees

23 Oct - 24 Oct

Steel City of South Side Flats Charming 2-Bedroom Unit

A living room with a brick fireplace, a round table, a blue sofa, a red chandelier, and two framed pictures on the walls.

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

A kitchen with white cabinets, a black refrigerator, a stove, and a hanging light fixture.

A hallway with a cityscape painting on the left, a kitchen area in the background, and a trash bin.

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

3-bedroom house in Southside Flats neighborhood of Pittsburgh.

South Side Flats

7.0 out of 10, Good, (2 reviews)

7.0/10

Good

(2 reviews)

"The house was very spacious! Everyone slept comfortably. The house is very conveniently located giving you the ability to access food on Carson as well as the highway."

Kyle S.

The price is AED 486

AED 486

AED 915 total

includes taxes & fees

20 Oct - 21 Oct

3-bedroom house in Southside Flats neighborhood of Pittsburgh.

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

A leather armchair with a wooden door and a staircase in the background.

A room with a television mounted on the wall, a wicker chair with blue cushions, a wooden cabinet with drawers, and a wall-mounted lamp.

A framed cityscape with a bridge reflected in water, a lamp, and a vent on the wall.

4. Pittsburgh Pennsylvania house

Pittsburgh Pennsylvania house

South Side Flats

6.0 out of 10, (2 reviews)

6.0/10

(2 reviews)

"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."

Adrian C.

The price is AED 343

AED 343

AED 940 total

includes taxes & fees

3 Nov - 4 Nov

Pittsburgh Pennsylvania house

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

A spice rack with labeled containers for sea salt, parsley, celery salt, and mint.

A bedroom with a bed, bedside table, lamp, and artwork on the wall.

A dining area with a table and chairs, a potted plant, and a wall-mounted light fixture.

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

Cozy Centralized 3bd 2bath House w/ Free Parking

South Side Flats

7.0 out of 10, Good, (2 reviews)

7.0/10

Good

(2 reviews)

"We had a wonderful stay and would absolutely book this property again. The home was clean, comfortable, and exactly as described, with everything we needed for a relaxing trip. The host was responsive, helpful, and made the whole experience easy from start to finish. Great location, thoughtful touches, and a smooth check-in/check-out process made this a fantastic stay. Highly recommend!"

Mark W.

The price is AED 918

AED 918

AED 2,220 total

includes taxes & fees

23 Oct - 24 Oct

Cozy Centralized 3bd 2bath House w/ Free Parking

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

A room with a dining table, chairs, a ceiling fan, a staircase, and a desk with a computer.

A bedroom with a bed, a desk, a chair, a nightstand, a lamp, and a ceiling fan.

A living room with a grey sofa, patterned cushions, a coffee table, and a ceiling fan.

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

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Allentown

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Very nice place perfect for my needs."

John

The price is AED 367

AED 367

AED 1,064 total

includes taxes & fees

13 Oct - 14 Oct

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

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

A spacious living room with a wooden floor, a large window with a view, a kitchen area with bar stools, and a cozy seating area with a rug and cushions.

A balcony with a view of a cityscape at night, featuring a lounge chair and a blanket.

A hotel room with a bed, pillows, a lamp, and a view of a city skyline through large windows.

7. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary

South Side Slopes

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 reviews)

"We had a great stay in this beautiful home! The host was super responsive and helpful. The home is spacious and well kept with amazing views of the city. The cherry on top was the driveway/parking area that accommodated our five vehicles. Great choice for our family get together!"

Mary H.

The price is AED 540

AED 540

AED 1,617 total

includes taxes & fees

12 Oct - 13 Oct

City Skyline - Outside decks - Contemporary

A city skyline with a view of various buildings, including a prominent UPMC building.

A city skyline with prominent buildings and a river.

A neatly made bed with a patterned throw, two bedside lamps, a window with a view of greenery, and framed artwork on the wall.

A modern living room with a large window, a sofa, a coffee table, a TV, and a bookshelf.

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

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

South Side Slopes

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Great stay! Rooms were comfortable and very clean. "

Anonymous traveler

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

A wooden deck with potted plants and a hanging fern.

A cozy living room with a fireplace, a dining table, and a comfortable seating area.

A wooden kitchen table with a floral centerpiece, a glass dome with cookies, and a blue polka-dotted dish.

A building with a snow-covered entrance and a visible sign indicating a loading zone.

9. 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, (22 reviews)

10/10

Exceptional

(22 reviews)

"Fantastic property. Intriguing history. Great location."

Kevin M.

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

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

A modern living room with two blue armchairs, a round marble coffee table, and a kitchen in the background.

A patio area with a round table and a fire pit.

A neatly made bed with a quilted cover, two bedside lamps, and a framed floral artwork on the wall.

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

Clean and comfortable 3BR home in the South Side neighborhood

South Side Slopes

10.0 out of 10, Exceptional, (45 reviews)

10/10

Exceptional

(45 reviews)

"This is such a cute house that is close to downtown. 10/10 would recommend this house. It was perfect for us!"

Amanda R.

Clean and comfortable 3BR home in the South Side neighborhood

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

A yellow building with a sign reading 'Monongahela Incline 1870'.

A kitchen with wooden cabinets, a black refrigerator, a countertop, and a television in the adjacent room.

A living room with a sectional sofa, a dining table with chairs, a kitchen area, and a large cityscape painting on the wall.

11. Urban Retreat with Garage on Mt. Washington

Urban Retreat with Garage on Mt. Washington

Mount Washington

9.8 out of 10, Exceptional, (98 reviews)

9.8/10

Exceptional

(98 reviews)

"Great place! Short walk to cool areas "

David M.

The price is AED 364

AED 364

AED 769 total

includes taxes & fees

26 Oct - 27 Oct

Urban Retreat with Garage on Mt. Washington

A modern kitchen with a central island, stainless steel appliances, and a seating area with a sofa and coffee table.

A modern kitchen with a built-in oven, a dining area with a white table and chairs, and a cozy seating area with a sofa and ottoman.

A modern kitchen with a flat-screen TV, a dining area with a white table, and a living room with a sofa and decorative pillows.

A modern living room with a white sofa, a coffee table, and a patterned rug. There is a kitchen area with white cabinets and a stainless steel range hood.

12. Not so tiny house with full kitchen & patio swing

Not so tiny house with full kitchen & patio swing

Garfield

9.6 out of 10, Exceptional, (73 reviews)

9.6/10

Exceptional

(73 reviews)

"Great little house. Easy to park. "

Anna B.

The price is AED 397

AED 397

AED 689 total

includes taxes & fees

12 Oct - 13 Oct

Not so tiny house with full kitchen & patio swing

A modern kitchen with wooden accents, a dining area with a table and chairs, and a gray sofa with patterned cushions.

A bedroom with a grey upholstered bed, white bedding, and decorative woven wall art.

A compact living space with a kitchenette, wooden wall, washing machine, and a dining area with a table and chairs.

A kitchen with a wooden shelf displaying framed artwork, a woven mirror, and a potted plant.

13. Lovely Strip District loft with free parking

Lovely Strip District loft with free parking

Strip District

10.0 out of 10, Exceptional, (42 reviews)

10/10

Exceptional

(42 reviews)

"Perfect stay"

M D.

The price is AED 397

AED 397

AED 689 total

includes taxes & fees

13 Oct - 14 Oct

Lovely Strip District loft with free parking

A living room with a fireplace, a sofa, a coffee table, and two paintings on the wall.

A residential backyard with a lawn, a pathway, and a small garden bed.

A bedroom with a bed, two chairs, a wooden wardrobe, floral curtains, and a painting on the wall.

A kitchen with white cabinets, a stove, a microwave, a dishwasher, and a sink.

14. Eclectic Historic Sunny Vista Home with City Views, Northshore

Eclectic Historic Sunny Vista Home with City Views, Northshore

North Side

9.6 out of 10, Exceptional, (41 reviews)

9.6/10

Exceptional

(41 reviews)

"Awesome place to stay. Clean and comfortable. Lisa was great. Easy access to public transportation downtown. We will be back again. Highly recommend this place."

William G.

The price is AED 290

AED 290

AED 777 total

includes taxes & fees

14 Oct - 15 Oct

Eclectic Historic Sunny Vista Home with City Views, Northshore

A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

A wooden coffee table with a book titled "VANGOC MONET" and a small potted plant.

A dining table set with plates, cutlery, and wine glasses, with two vases of flowers in the background.

A modern kitchen with a white island, wooden staircase, and a dining area with a blue sofa.

15. By PPG,Duquesne,Mercy |Exquisite, New |Free Parkin

By PPG,Duquesne,Mercy |Exquisite, New |Free Parkin

Bluff

10.0 out of 10, Exceptional, (17 reviews)

10/10

Exceptional

(17 reviews)

"Communication was great! Easy location to get to and plenty of things to do around it. Very clean and would definitely stay here again!"

Shane M.

The price is AED 735

AED 735

AED 1,706 total

includes taxes & fees

14 Oct - 15 Oct

By PPG,Duquesne,Mercy |Exquisite, New |Free Parkin

A modern living room with a fireplace, a staircase, and a view of the outdoors.

A bedroom with a bed, a nightstand, a lamp, a hanging plant, and a view of the outside through large windows.

A dining area with a wooden staircase, a black and white patterned rug, and a large decorative wall piece.

A spacious living room with a brick wall, a fireplace, a staircase, and a modern staircase.

16. 1207 Ocala - Boat House - North Side

1207 Ocala - Boat House - North Side

North Side

10.0 out of 10, Exceptional, (38 reviews)

10/10

Exceptional

(38 reviews)

"Great place. Parking a bit of a pain, but everything was perfect."

Edward C.

The price is AED 419

AED 419

AED 985 total

includes taxes & fees

12 Oct - 13 Oct

1207 Ocala - Boat House - North Side

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

A wooden table with a white vase containing yellow flowers, a brick wall with an arched window, and metal chairs.

A bathroom with a wooden vanity, a large mirror, a copper basin, and a brick wall.

A bedroom with a bed, a bedside table, a lamp, a mirror, and wall art.

17. Park Free★Amazing Space★Professionally Cleaned!

Park Free★Amazing Space★Professionally Cleaned!

North Side

10.0 out of 10, Exceptional, (43 reviews)

10/10

Exceptional

(43 reviews)

"Amazing place to stay while in Pittsburgh - extremely clean and close to many cool neighborhoods and places to visit! "

Jennifer Y.

Park Free★Amazing Space★Professionally Cleaned!

A modern kitchen with white cabinetry, a central island, and a dining area with a clear table.

A modern living room with a grey sofa, a round coffee table, and a staircase leading to an upper floor.

A bedroom with a large bed, a nightstand, a wall-mounted artwork, and a door leading to another room.

A room with two pink chairs, a small table, a window with blinds, a decorative wall piece, and a brick wall.

18. Free Parking★Walk Everywhere!★2 Private bathrooms!

Free Parking★Walk Everywhere!★2 Private bathrooms!

North Side

9.8 out of 10, Exceptional, (49 reviews)

9.8/10

Exceptional

(49 reviews)

"Great little place, close to museums and other sites."

Kelly D.

Free Parking★Walk Everywhere!★2 Private bathrooms!

A grassy outdoor area with a wooden bench, a stone statue, and a wooden fence.

A kitchen with dark blue cabinets, a black refrigerator, a stove, and a dining table with chairs.

A room with a patterned rug, a chair, a small table, a wicker basket, a dark wooden cabinet, and a window with decorative items.

A bedroom with a bed, a door to another room, and a hallway leading to a staircase.

19. Explore Pittsburgh from a Modern, Hip Bungalow

Explore Pittsburgh from a Modern, Hip Bungalow

North Side

9.6 out of 10, Exceptional, (75 reviews)

9.6/10

Exceptional

(75 reviews)

"Great location. Would stay again. "

Yukiko M.

The price is AED 257

AED 257

AED 686 total

includes taxes & fees

20 Oct - 21 Oct

Explore Pittsburgh from a Modern, Hip Bungalow

A modern living room with a fireplace, a green sofa, a wooden coffee table, and a dining area with a wooden table and chairs.

A modern living room with a large bed, green sofas, a wooden coffee table, and a TV mounted on the wall.

A modern bedroom with a bed, bedside tables, a TV, and a balcony with plants.

A modern kitchen with a brick wall, wooden cabinets, and a large dining table with a macrame runner.

20. Strip District Studio-Free Parking-Natural Light

Strip District Studio-Free Parking-Natural Light

Strip District

9.2 out of 10, Wonderful, (33 reviews)

9.2/10

Wonderful

(33 reviews)

"We had a great stay - it was a beautiful place and convenient location. It could get somewhat noisy, but we did not have any trouble sleeping through the night. Would stay again for another Pittsburgh trip!"

Martene B.

The price is AED 397

AED 397

AED 689 total

includes taxes & fees

14 Oct - 15 Oct

Strip District Studio-Free Parking-Natural Light

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

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

10/10 Excellent

"Experience was overall great. The cleanliness, the service, breakfast, and parking were all very pleasant and convenient. It wasn’t far at all from the main attractions we had planned to go to, so even if you Uber or Lyft it wouldn’t be expensive."

Ingrid 1-night trip

Posted 1 hour ago

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

The Landing Hotel at Rivers Casino

10/10 Excellent

"Excellent stay. Breakfast had plenty of choices and was delicious."

Monica 3-night trip

Posted 14 hours ago

The Landing Hotel at Rivers Casino

Hilton Garden Inn Pittsburgh Downtown

10/10 Excellent

"Convenient & clean hotel."

Zachary 2-night trip

Posted 16 hours ago

Hilton Garden Inn Pittsburgh Downtown

Omni William Penn Hotel

10/10 Excellent

"All the eateries onsite are wonderful."

FRANK 2-night trip

Posted 23 hours ago

Omni William Penn Hotel

Joinery Hotel Pittsburgh, Curio Collection by Hilton

8/10 Good

"Mediocre restaurant"

Robert 3-night trip

Posted 2 days ago

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Hyatt Regency Pittsburgh International Airport

10/10 Excellent

"Matt the bartender always is welcoming & is excellent at his service"

Megan 1-night trip

Posted 2 days ago

Hyatt Regency Pittsburgh International Airport

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Search Vacation Homes in South Side

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Side vacation homes

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

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

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

4. Pittsburgh Pennsylvania house

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

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

7. City Skyline - Outside decks - Contemporary

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

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

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

11. Urban Retreat with Garage on Mt. Washington

12. Not so tiny house with full kitchen & patio swing

13. Lovely Strip District loft with free parking

14. Eclectic Historic Sunny Vista Home with City Views, Northshore

15. By PPG,Duquesne,Mercy |Exquisite, New |Free Parkin

16. 1207 Ocala - Boat House - North Side

17. Park Free★Amazing Space★Professionally Cleaned!

18. Free Parking★Walk Everywhere!★2 Private bathrooms!

19. Explore Pittsburgh from a Modern, Hip Bungalow

20. Strip District Studio-Free Parking-Natural Light

Find vacation rentals that suit your style

Top South Side Hotel Reviews

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

Explore a world of travel with Expedia