South Side Holiday Houses

South Side Holiday Homes
Pennsylvania
United States of America
Holiday Homes
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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.

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

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

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.

The price is NZ$505

NZ$505

includes taxes & fees

13 Oct - 14 Oct

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.

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 NZ$507

NZ$507

includes taxes & fees

20 Oct - 21 Oct

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 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 NZ$426

NZ$426

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 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.

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

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 NZ$444

NZ$444

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

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 NZ$1,073

NZ$1,073

includes taxes & fees

12 Oct - 13 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 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 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 NZ$507

NZ$507

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 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 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 NZ$764

NZ$764

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

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 city skyline with prominent buildings and a river.

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 traveller

The price is NZ$726

NZ$726

includes taxes & fees

13 Oct - 14 Oct

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

A wooden deck with potted plants and a hanging fern.

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.

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

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.

The price is NZ$1,136

NZ$1,136

includes taxes & fees

14 Oct - 15 Oct

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 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.

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

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

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'.

11. Urban Retreat with Garage on Mt. Washington

Urban Retreat with Garage on Mt. Washington

Mount Washington

9.8 out of 10, Exceptional, (96 reviews)

9.8/10

Exceptional

(96 reviews)

"Great place! Short walk to cool areas "

David M.

The price is NZ$385

NZ$385

includes taxes & fees

12 Oct - 13 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 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.

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 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.

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 NZ$330

NZ$330

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

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

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

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)

"Great location and really nice property."

Tracy H.

The price is NZ$328

NZ$328

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

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

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 NZ$354

NZ$354

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

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.

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 NZ$913

NZ$913

includes taxes & fees

13 Oct - 14 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 dining area with a wooden staircase, a black and white patterned rug, and a large decorative wall piece.

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

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

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 NZ$410

NZ$410

includes taxes & fees

14 Oct - 15 Oct

1207 Ocala - Boat House - North Side

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

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

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

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

17. Park Free★Amazing Space★Professionally Cleaned!

Park Free★Amazing Space★Professionally Cleaned!

North Side

10.0 out of 10, Exceptional, (42 reviews)

10/10

Exceptional

(42 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 NZ$400

NZ$400

includes taxes & fees

14 Oct - 15 Oct

Park Free★Amazing Space★Professionally Cleaned!

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

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

A modern living room with a grey sofa, pink chairs, a glass coffee table, and a patterned rug.

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

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.

The price is NZ$628

NZ$628

includes taxes & fees

16 Oct - 17 Oct

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

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

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 NZ$332

NZ$332

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

A kitchen with a brick wall, a stove, oven, microwave, and a window with a view.

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 NZ$328

NZ$328

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

Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent

"Great quiet and dark room that was super comfortable"

Kimberly 1-night trip

Posted 2 hours ago

Drury Plaza Hotel Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

8/10 Good

"Great location. Staff was helpful and the room was very nice."

Michael 1-night trip

Posted 3 hours ago

Wyndham Grand Pittsburgh Downtown

Pittsburgh Marriott City Center

10/10 Excellent

"Perfect location downtown for a hockey game or concert. Valet parking is great. I left an item in my room and the claims process was very easy, staff was helpful and I was able to pick up my item a couple of days later!"

Mackenzie 1-night trip

Posted 4 hours ago

Pittsburgh Marriott City Center

Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG

10/10 Excellent

"Great spot, clean and very friendly staff"

Nadine 1-night trip

Posted 12 hours ago

Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG

Hyatt Regency Pittsburgh International Airport

10/10 Excellent

"Great staff"

James 2-night trip

Posted 13 hours ago

Hyatt Regency Pittsburgh International Airport

DoubleTree by Hilton Pittsburgh - Green Tree

10/10 Excellent

"Such a lovely hotel. So close to everything. Rooms were spotless, staff were friendly, parking was abundant, and always felt safe as mother traveling with small children. When we go back to Pittsburgh this is where we will stay."

GINA 2-night trip

Posted 2 days ago

DoubleTree by Hilton Pittsburgh - Green Tree

Hilton Garden Inn Pittsburgh Downtown

8/10 Good

"Great location"

Jon 1-night trip

Posted 2 days ago

Hilton Garden Inn Pittsburgh Downtown

Find out more about South Side

South Side Holiday Homes information

Number of reviews	613
Accommodation	738 Holiday Homes
Lowest Price	NZ$328
Highest Price	NZ$1,136

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Book Holiday Homes in South Side on Expedia.com

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. 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 holiday rentals that suit your style

Top South Side Hotel Reviews

Drury Plaza Hotel Pittsburgh Downtown

Find out more about South Side

South Side Holiday Homes information

Explore a world of travel with Expedia