South Side, PA Vacation Homes from AED 592

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

A living room with a sofa, a coffee table, a lamp, and a chair.

A neatly made bed with rolled towels, a decorative lamp, and patterned pillows.

A kitchen with white subway tiles, a coffee maker, and a stack of black coffee mugs.

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

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

South Side Flats

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"The property was outstanding, nicely appointed and quite comfortable. Close to downtown without being IN downtown, thus very well-located for everywhere we needed to be. Service was excellent, our questions were answered promptly and with the right amount of detail. "

Butch K.

The price is AED 313

AED 313

AED 753 total

includes taxes & fees

2 Nov - 3 Nov

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

A living room with a sofa, a flat-screen TV, and a kitchen area with wooden cabinets and a refrigerator.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a round table and chairs.

A kitchen with a central island, pendant lighting, a clock on the wall, and a dining area with chairs and a table.

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

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

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

South Side Slopes

The price is AED 382

AED 382

AED 824 total

includes taxes & fees

1 Nov - 2 Nov

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

A black electronic device with multiple ports and a remote control on a wooden surface.

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

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

3. 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, (12 reviews)

10/10

Exceptional

(12 reviews)

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

Manuel M.

The price is AED 367

AED 367

AED 1,010 total

includes taxes & fees

4 Nov - 5 Nov

Iron City of South Side Flats Charming 2-bedroom Unit

A room with a flat-screen TV mounted on the wall, a wooden floor, and a white door leading to another room.

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

4. 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 374

AED 374

AED 1,017 total

includes taxes & fees

4 Nov - 5 Nov

Steel City of South Side Flats Charming 2-Bedroom Unit

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

A living room with a brick fireplace, a round coffee table, a dark sofa, a television, and a cityscape painting.

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

A room with a cityscape painting, a piano, a dining table with chairs, and a window with blinds.

5. 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 430

AED 430

AED 843 total

includes taxes & fees

2 Nov - 3 Nov

3-bedroom house in Southside Flats neighborhood of Pittsburgh.

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

A living room with a flat-screen TV mounted on the wall, a sofa, a coffee table, and two side tables.

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

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

6. 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 2,183 total

includes taxes & fees

9 Nov - 10 Nov

Cozy Centralized 3bd 2bath House w/ Free Parking

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.

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

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

7. 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 453

AED 453

AED 1,081 total

includes taxes & fees

16 Nov - 17 Nov

Pittsburgh Pennsylvania house

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

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

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 kitchen with a central island, wooden cabinets, and pendant lighting.

8. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary

South Side Slopes

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 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 450

AED 450

AED 1,491 total

includes taxes & fees

28 Oct - 29 Oct

City Skyline - Outside decks - Contemporary

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 backyard with a circular fire pit surrounded by rocks and logs, a wooden deck, and a red pathway.

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

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

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Allentown

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"Very nice place perfect for my needs."

John

The price is AED 367

AED 367

AED 1,173 total

includes taxes & fees

2 Nov - 3 Nov

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

A compact kitchen with white cabinets, a stove, a sink, and wooden stools.

A green building with a door, steps, and a mailbox.

A closet with three shelves, a hanging rod, and a door with a brass handle.

A white washing machine with a blue detergent bottle on top, a warning label, and a chair nearby.

10. Cozy Loft Studio in a Triplex, near SouthSideWorks

Cozy Loft Studio in a Triplex, near SouthSideWorks

South Side Flats

8.0 out of 10, Very good, (2 reviews)

8.0/10

Very good

(2 reviews)

"Great communication"

Clay B.

The price is AED 248

AED 248

AED 592 total

includes taxes & fees

1 Nov - 2 Nov

Cozy Loft Studio in a Triplex, near SouthSideWorks

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

A neatly made bed with white linens, a green knitted throw, and a rolled white towel. There are two pillows, one green and one gold. A small bedside table with a lamp and a plant is visible.

An outdoor patio with a dining table, chairs, and an umbrella.

A modern dining area with a black wall, a stainless steel refrigerator, and a dining table set with blue napkins and white plates.

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

Central 5BD Getaway - Spacious Home w/ BBQ

South Side Flats

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Great host and property "

Eric G.

The price is AED 1,129

AED 1,129

AED 2,387 total

includes taxes & fees

28 Oct - 29 Oct

Central 5BD Getaway - Spacious Home w/ BBQ

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

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

A modern living room with a sofa, a coffee table, a TV, and a staircase.

A city skyline with prominent buildings and a river.

12. 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, (7 reviews)

10/10

Exceptional

(7 reviews)

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

Anonymous traveler

The price is AED 655

AED 655

AED 1,540 total

includes taxes & fees

28 Oct - 29 Oct

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

A modern kitchen with dark cabinets, stainless steel appliances, a central island with stools, and a chandelier.

A modern bedroom with a large bed, a hanging light fixture, a framed picture on the wall, and a window with blinds.

A modern living room with a geometric-patterned sofa, a grey armchair, and a large window with a view of the street.

An outdoor patio with a wooden deck, a table with chairs, a fire feature, string lights, and a brick wall in the background.

13. 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, (70 reviews)

9.8/10

Exceptional

(70 reviews)

"Great location and an amazing value"

Tony J.

The price is AED 1,403

AED 1,403

AED 2,490 total

includes taxes & fees

22 Nov - 23 Nov

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

A dining area with a long table set for a meal, a colorful abstract wall, and a retro arcade machine in the background.

A modern living room with a green sofa, a black armchair, and a wooden sculpture. There is a colorful arcade machine on the left and a window with a view of buildings outside.

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

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

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

Pittsburgh House with Hot Tub, Patio & Free Parking!

South Side Flats

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Perfect vibes for a small girls trip. Great location. Such a fun place, thanks for the small details!"

Sara P.

Pittsburgh House with Hot Tub, Patio & Free Parking!

A wooden deck with potted plants and a hanging fern.

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.

A spacious kitchen with a central island, wooden bar stools, a large refrigerator, and a ceiling fan.

15. 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.

The price is AED 1,803

AED 1,803

AED 3,046 total

includes taxes & fees

1 Nov - 2 Nov

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

A kitchen with wooden cabinets, a stainless steel refrigerator, a countertop, and a sliding glass door leading to a balcony.

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

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.

16. Urban Retreat with Garage on Mt. Washington

Urban Retreat with Garage on Mt. Washington

Mount Washington

9.8 out of 10, Exceptional, (100 reviews)

9.8/10

Exceptional

(100 reviews)

"Accurate pictures, very clean! Easy check in !! Will definitely stay Again!!"

Jeff D.

The price is AED 367

AED 367

AED 773 total

includes taxes & fees

2 Nov - 3 Nov

Urban Retreat with Garage on Mt. Washington

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

A hallway with a blue door, a welcome sign, a bench with a patterned cushion, and a kitchen area in the background.

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

A dining area with a wooden table and four chairs, a potted plant, and a framed picture on the wall.

17. Relax & Feel At Home During Your Pittsburgh Stay

Relax & Feel At Home During Your Pittsburgh Stay

Carrick

9.4 out of 10, Exceptional, (32 reviews)

9.4/10

Exceptional

(32 reviews)

"we pretty much just traveled from appointments back to the house. but we were very well pleased with our accommodations"

Kay K.

The price is AED 408

AED 408

AED 857 total

includes taxes & fees

1 Nov - 2 Nov

Relax & Feel At Home During Your Pittsburgh Stay

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 modern kitchen with wooden paneling, a glass shower enclosure, and a microwave.

18. Lovely Strip District loft with free parking

Lovely Strip District loft with free parking

Strip District

10.0 out of 10, Exceptional, (43 reviews)

10/10

Exceptional

(43 reviews)

"Perfect stay"

M D.

The price is AED 397

AED 397

AED 681 total

includes taxes & fees

29 Oct - 30 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 bedroom with a bed, two chairs, a wooden wardrobe, floral curtains, and a painting on the wall.

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

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

19. 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, (42 reviews)

9.6/10

Exceptional

(42 reviews)

"Great location! Close proximity to the city, but secluded in the mountain. Great place to stay for a series at PNC park."

Alli S.

The price is AED 290

AED 290

AED 769 total

includes taxes & fees

3 Nov - 4 Nov

Eclectic Historic Sunny Vista Home with City Views, Northshore

A kitchen counter with white tiles, a wooden shelf, and a plant in a wire basket.

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

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 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, (35 reviews)

9.2/10

Wonderful

(35 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 681 total

includes taxes & fees

29 Oct - 30 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

8/10 Good

"We stayed one night. Only interacted with staff at check in but they were friendly. We didn’t use any of the amenities. The room was clean and neat."

Katie 1-night trip

Posted 1 hour ago

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

Hyatt Place Pittsburgh-North Shore

10/10 Excellent

"Great pick for a hotel close to the beautiful bridge u can walk over to go to down town"

Destiny 2-night trip

Posted 1 hour ago

Hyatt Place Pittsburgh-North Shore

DoubleTree by Hilton Pittsburgh - Green Tree

10/10 Excellent

"Very comfortable and quiet room"

Catherine 6-night trip

Posted 2 hours ago

DoubleTree by Hilton Pittsburgh - Green Tree

Cambria Hotel Pittsburgh - Downtown

10/10 Excellent

"Best part was it was next to PPG arena. Could have been cleaner a little more updater. Room has a lot of wear but staff was very helpful and friendly and if I staying at hotel parking should be part of the stay. Not extra. We are not walking there."

Patti 1-night trip

Posted 2 hours ago

Cambria Hotel Pittsburgh - Downtown

TRYP by Wyndham Pittsburgh/Lawrenceville

10/10 Excellent

"Zero complaints loved this place, totally would rebook again. Great dinner spot on ground level with GREAT prices and a coffee stand in the morning but was not able to try I left before 7 am. Great place to stay for a couple night!"

Jorden 1-night trip

Posted 2 hours ago

TRYP by Wyndham Pittsburgh/Lawrenceville

SpringHill Suites by Marriott Pittsburgh Southside Works

8/10 Good

"please declare your parking fees much more clearly and your lack of street parking. the lack of operable windows in the room made it difficult to dissipate the chemical smell of the air freshener used."

Victoria 3-night trip

Posted 3 hours ago

SpringHill Suites by Marriott Pittsburgh Southside Works

Pittsburgh Marriott City Center

10/10 Excellent

"It was in a great location. I could easily walk everywhere I wanted to go: Penguins game, across the Warhol bridge or to the Strip."

Tammy 3-night trip

Posted 3 hours ago

Pittsburgh Marriott City Center

Wyndham Grand Pittsburgh Downtown

10/10 Excellent

"great staff and convient location"

Jeanette 1-night trip

Posted 4 hours ago

Wyndham Grand Pittsburgh Downtown

Omni William Penn Hotel

10/10 Excellent

"Our first time stay and everything was excellent, including the food. Our Ambassador was very helpful and accomodating."

Brenda 2-night trip

Posted 1 day ago

Omni William Penn Hotel

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

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

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

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

5. 3-bedroom house in Southside Flats neighborhood of Pittsburgh.

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

7. Pittsburgh Pennsylvania house

8. City Skyline - Outside decks - Contemporary

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

10. Cozy Loft Studio in a Triplex, near SouthSideWorks

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

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

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

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

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

16. Urban Retreat with Garage on Mt. Washington

17. Relax & Feel At Home During Your Pittsburgh Stay

18. Lovely Strip District loft with free parking

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

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