Holiday Homes in South Side

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Our top choices for South Side holiday homes

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
South Side Flats
7.6 out of 10, Good, (10 reviews)
"Home was very comfy children enjoyed there stay I was able to relax and feel comfortable stay I would definitely book again."
United States
bonita f.
The price is €204
includes taxes & fees
3 Mar - 4 Mar
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

King Bed | Free Parking | Arcade | Fire Pit

King Bed | Free Parking | Arcade | Fire Pit
South Side Flats
9.8 out of 10, Exceptional, (26 reviews)
"Great location to the things we wanted to go and do We celebrated my wife’s 60 birthday "
United States
Scott A.
The price is €355
includes taxes & fees
1 Mar - 2 Mar
King Bed | Free Parking | Arcade | Fire Pit

Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!

Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!
South Side Slopes
10.0 out of 10, Exceptional, (16 reviews)
"Great stay! Very good location to get to the city and great restaurants. Amazing view! The host was very nice and great to work with. "
United States
Eric A.
The price is €572
includes taxes & fees
26 Feb - 27 Feb
Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!

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

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
South Side Flats
The price is €174
includes taxes & fees
26 Feb - 27 Feb
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

Iron City of South Side Flats Charming 2-bedroom Unit

Iron City of South Side Flats Charming 2-bedroom Unit
South Side Flats
The price is €262
includes taxes & fees
1 Mar - 2 Mar
Iron City of South Side Flats Charming 2-bedroom Unit

Steel City of South Side Flats Charming 2-Bedroom Unit

Steel City of South Side Flats Charming 2-Bedroom Unit
South Side Flats
The price is €272
includes taxes & fees
8 Mar - 9 Mar
Steel City of South Side Flats Charming 2-Bedroom Unit

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, (2 reviews)
"Everything was great. We would definitely stay here again. "
United States
Jason M.
The price is €304
includes taxes & fees
3 Mar - 4 Mar
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views

Modern 5BR Retreat • Multiple En Suites • Prime South Side Location • Walkable

Modern 5BR Retreat • Multiple En Suites • Prime South Side Location • Walkable
South Side Flats
10.0 out of 10, Exceptional, (1 review)
"The place was very clean and well-equipped, within walking distance of food and entertainment. Jennifer is very responsive and an excellent communicator."
United States
fady c.
The price is €349
includes taxes & fees
26 Feb - 27 Feb
Modern 5BR Retreat • Multiple En Suites • Prime South Side Location • Walkable

City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
10.0 out of 10, Exceptional, (4 reviews)
"We appreciated the way most everything was as shown in photos and loved the 4 furnished decks. The owner quickly responded to our needs and questions. Nice to have parking not on street."
United States
Deborah C.
The price is €352
includes taxes & fees
26 Feb - 27 Feb
City Skyline - Outside decks - Contemporary

Central 5BD Getaway - Spacious Home w/ BBQ

Central 5BD Getaway - Spacious Home w/ BBQ
South Side Flats
10.0 out of 10, Exceptional, (10 reviews)
"Great host and property "
United States
Eric G.
Central 5BD Getaway - Spacious Home w/ BBQ

King Bed - BBQ & Hot Tub - Centrally Located

King Bed - BBQ & Hot Tub - Centrally Located
South Side Flats
8.0 out of 10, Very good, (2 reviews)
"It was an excellent stay and a very accurate property description. "
United States
chad s.
The price is €337
includes taxes & fees
10 Mar - 11 Mar
King Bed - BBQ & Hot Tub - Centrally Located

Hot Tub | King Bed | Games | Free Parking

Hot Tub | King Bed | Games | Free Parking
South Side Flats
10.0 out of 10, Exceptional, (6 reviews)
"Perfect vibes for a small girls trip. Great location. Such a fun place, thanks for the small details!"
United States
Sara P.
The price is €505
includes taxes & fees
8 Mar - 9 Mar
Hot Tub | King Bed | Games | Free Parking

Pittsburgh Pennsylvania house

Pittsburgh Pennsylvania house
South Side Flats
6.0 out of 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."
United States
Adrian C.
The price is €234
includes taxes & fees
2 Mar - 3 Mar
Pittsburgh Pennsylvania house

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Allentown
The price is €435
includes taxes & fees
3 Mar - 4 Mar
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

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, (20 reviews)
"Fantastic property. Intriguing history. Great location."
United States
Kevin M.
The price is €507
includes taxes & fees
27 Feb - 28 Feb
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

Strip District Studio-Free Parking-Natural Light

Strip District Studio-Free Parking-Natural Light
Strip District
9.4 out of 10, Exceptional, (26 reviews)
"Spacious. Great kitchen. Very homey and convenient. The host was incredibly attentive. I. Loved the shower. "
United States
Dede A.
The price is €160
includes taxes & fees
2 Mar - 3 Mar
Strip District Studio-Free Parking-Natural Light

Lovely Strip District loft with free parking

Lovely Strip District loft with free parking
Strip District
10.0 out of 10, Exceptional, (28 reviews)
"Excellent location. Very clean and well kept apartment. "
United States
George & Audrey U.
The price is €160
includes taxes & fees
2 Mar - 3 Mar
Lovely Strip District loft with free parking

Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!
Plum
10.0 out of 10, Exceptional, (17 reviews)
"It was a very nice property, very clean, great neighborhood and area."
United States
A. Ben K.
The price is €254
includes taxes & fees
26 Feb - 27 Feb
Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

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

307 37th St · Lawrenceville Row House - Walk to Everything!
Lawrenceville
9.4 out of 10, Exceptional, (40 reviews)
"We loved staying here! The unit was in a quiet and safe location, it was clean and spacious, and had everything we needed. I would highly recommend it. "
United States
Melissa S.
The price is €164
includes taxes & fees
25 Mar - 26 Mar
307 37th St · Lawrenceville Row House - Walk to Everything!

The Light Room

The Light Room
McKeesport
9.6 out of 10, Exceptional, (5 reviews)
"The house has a very peaceful atmosphere."
United States
Susan G.
The price is €162
includes taxes & fees
28 Feb - 1 Mar
The Light Room
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

Find out more about South Side

South Side Holiday Homes information

Number of reviews
192
Accommodation
626 Holiday Homes
Lowest Price
€160
Highest Price
€572

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