South Side Holiday Homes from €169: Search Top House Rentals

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Our top choices for South Side holiday homes

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

A building with a black door, a bench, and a sign with the number 2400.

A living room with a sofa, a coffee table, and a TV. There is a kitchen area in the background with a dining table and chairs.

A modern kitchen with a bar area, including a bar counter and stools.

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

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

South Side Slopes

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

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

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.

Steel City of South Side Flats Charming 2-Bedroom Unit

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

A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a built-in oven.

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

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

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

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

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.

4. 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 €219

€219

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

A neatly made bed with a yellow throw blanket, a modern headboard, and a wall-mounted sign that reads "LET'S STAY N BED".

5. 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 €227

€227

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 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.

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.

Cozy Centralized 3bd 2bath House w/ Free Parking

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

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

7. 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.

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

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

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

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

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

8. 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 €258

€258

includes taxes & fees

10 Nov - 11 Nov

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

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

A bar area with a dark hexagonal wall pattern, a wooden bar counter, and a sign that reads "STEEL CITY".

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

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

9. 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)

"Stayed for a guys weekend with the family, everybody was very happy with the accommodations and the proximity to restaurants and such. Phil and Dotty were two of the most gracious responsive hosts I’ve ever had the pleasure of dealing with. Would def rent again if back in Pittsburgh"

Sean O.

Central 5BD Getaway - Spacious Home w/ BBQ

A wooden deck with potted plants and a hanging fern.

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.

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

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

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

11. 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 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.

A kitchen with wooden cabinets, a microwave, a stove, a dishwasher, and a toaster.

12. 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 €190

€190

includes taxes & fees

26 Oct - 27 Oct

Urban Retreat with Garage on Mt. Washington

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

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

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

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

13. 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 €190

€190

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

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

A living room with a sofa, armchair, dining table, and TV.

14. 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 €417

€417

includes taxes & fees

14 Oct - 15 Oct

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

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

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.

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

15. 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 €169

€169

includes taxes & fees

13 Oct - 14 Oct

Lovely Strip District loft with free parking

Luxurious kitchen with gas cooker, a blender, coffee maker, oven, etc.
Feel at home without being at home!

A bedroom with a bed, a ceiling fan, a potted plant, and a sliding door to a bathroom.

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

A staircase with a black railing, a framed picture of a tree, a black door with a window, and a white couch with a throw pillow.

16. 4BR 4BA Urban Oasis in Mt Washington

4BR 4BA Urban Oasis in Mt Washington

Mount Washington

9.8 out of 10, Exceptional, (35 reviews)

9.8/10

Exceptional

(35 reviews)

"We had a wonderful holiday week. "

Teri A.

4BR 4BA Urban Oasis in Mt Washington

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

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

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

A dining area with a brick fireplace, a spiral staircase, and a bookshelf with various items.

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.

The price is €206

€206

includes taxes & fees

12 Oct - 13 Oct

Park Free★Amazing Space★Professionally Cleaned!

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

A living room with a grey sofa, a television, and a fireplace.

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

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

18. 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.

1207 Ocala - Boat House - North Side

A modern kitchen with white cabinets, a wooden floor, and a patterned rug. There are two windows with blinds, a small side table with a lamp, and a potted plant on the wall.

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 apartment with a kitchenette, a dining area, and a bedroom.

19. 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 €172

€172

includes taxes & fees

12 Oct - 13 Oct

Not so tiny house with full kitchen & patio swing

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.

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

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

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.

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

Hyatt Regency Pittsburgh International Airport

10/10 Excellent

"it was fine. I recommend it. They need some porters."

Michael 1-night trip

Posted 2 hours ago

Hyatt Regency Pittsburgh International Airport

DoubleTree by Hilton Pittsburgh - Green Tree

10/10 Excellent

"Respectful Staff Very kind Only negative is there’s no microwave in the room, however a microwave was available to use in the lobby"

Mario 2-night trip

Posted 9 hours ago

DoubleTree by Hilton Pittsburgh - Green Tree

The Landing Hotel at Rivers Casino

10/10 Excellent

"My fiancé and I love it here! That’s all"

Stacey 1-night trip

Posted 12 hours ago

The Landing Hotel at Rivers Casino

Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent

"Hot water clean amenities great food good staff Thank you"

Gerard 1-night trip

Posted 15 hours ago

Drury Plaza Hotel Pittsburgh Downtown

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 23 hours ago

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

Omni William Penn Hotel

10/10 Excellent

"All the eateries onsite are wonderful."

FRANK 2-night trip

Posted 2 days ago

Omni William Penn Hotel

Find out more about South Side

South Side Holiday Homes information

Number of reviews	530
Accommodation	717 Holiday Homes
Lowest Price	€169
Highest Price	€417

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Pittsburgh Holiday Rentals

Holiday Homes in South Side

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Side holiday homes

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

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

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

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

5. Pittsburgh Pennsylvania house

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

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

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

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

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

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

12. Urban Retreat with Garage on Mt. Washington

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

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

15. Lovely Strip District loft with free parking

16. 4BR 4BA Urban Oasis in Mt Washington

17. Park Free★Amazing Space★Professionally Cleaned!

18. 1207 Ocala - Boat House - North Side

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

20. Strip District Studio-Free Parking-Natural Light

Find holiday rentals that suit your style

Top South Side Hotel Reviews

Hyatt Regency Pittsburgh International Airport

Find out more about South Side

South Side Holiday Homes information

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