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Holiday Homes in South Side

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for South Side holiday homes

1 bedroom, in-room safe, desk, iron/ironing board

Cozy Loft Studio in a Triplex, near SouthSideWorks

Cozy Loft Studio in a Triplex, near SouthSideWorks
South Side Flats
10.0 out of 10, Exceptional, (1 review)
"First time using VRBO and I couldn’t have asked for a better experience. I stayed one night at SouthSide Works in Pittsburgh for 145, which kept my whole trip well under budget. The place had everything I needed, the location was lively with plenty to do nearby, and the hosts were genuinely lovely people. No complaints at all. Had an amazing stay! five stars! and I’ll happily recommend it to others!"
United States
Sriganesh K.
The price is NZ$257
includes taxes & fees
19 July - 20 July
Cozy Loft Studio in a Triplex, near SouthSideWorks
Property grounds

South Side Vibe! Pittsburgh's best location

South Side Vibe! Pittsburgh's best location
South Side Flats
9.6 out of 10, Exceptional, (14 reviews)
"Nice place"
United States
Andres M.
The price is NZ$399
includes taxes & fees
13 July - 14 July
South Side Vibe! Pittsburgh's best location
Interior

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

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
South Side Flats
9.4 out of 10, Exceptional, (3 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. "
United States
Butch K.
The price is NZ$378
includes taxes & fees
3 Aug - 4 Aug
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
Private kitchen

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, (1 review)
"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."
United States
Heather B.
The price is NZ$487
includes taxes & fees
22 July - 23 July
Steel City of South Side Flats Charming 2-Bedroom Unit
Private kitchen

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Allentown
10.0 out of 10, Exceptional, (1 review)
"Very nice place perfect for my needs."
United States
John
The price is NZ$506
includes taxes & fees
12 July - 13 July
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
2 bedrooms, desk, iron/ironing board, travel cot

Trendy 2BR Near Carson Street | Free Parking

Trendy 2BR Near Carson Street | Free Parking
South Side Flats
The price is NZ$780
includes taxes & fees
16 July - 17 July
Trendy 2BR Near Carson Street | Free Parking
Interior

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.
King Bed - BBQ & Hot Tub - Centrally Located
Smart TV

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, (7 reviews)
The price is NZ$505
includes taxes & fees
20 July - 21 July
Iron City of South Side Flats Charming 2-bedroom Unit
Dining

3-bedroom house in Southside Flats neighborhood of Pittsburgh.

3-bedroom house in Southside Flats neighborhood of Pittsburgh.
South Side Flats
The price is NZ$464
includes taxes & fees
21 July - 22 July
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
Outdoor dining

City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
9.8 out of 10, Exceptional, (6 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.
City Skyline - Outside decks - Contemporary
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy Cabin in the City All the comforts of home, parking, pets allowed. Sleeps 8

Cozy Cabin in the City All the comforts of home, parking, pets allowed. Sleeps 8
South Side Flats
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful gem in the Southside. A quick walk to Carson street or a short Uber to downtown/the stadiums made this a great spot to stay. Host was super communicative and everything was as advertised. Would definitely recommend staying here!"
United States
Hannah S.
The price is NZ$673
includes taxes & fees
12 July - 13 July
Cozy Cabin in the City All the comforts of home, parking, pets allowed. Sleeps 8
Dining

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)
"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!"
United States
Mark W.
The price is NZ$942
includes taxes & fees
23 July - 24 July
Cozy Centralized 3bd 2bath House w/ Free Parking
Exterior detail

Central 5BD Getaway - Spacious Home w/ BBQ

Central 5BD Getaway - Spacious Home w/ BBQ
South Side Flats
10.0 out of 10, Exceptional, (11 reviews)
"The hosts were very welcoming!"
United States
Chloe B.
Central 5BD Getaway - Spacious Home w/ BBQ
Property grounds

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)
"Great stay! Rooms were comfortable and very clean. "
United States
Anonymous traveller
The price is NZ$884
includes taxes & fees
26 July - 27 July
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
Outdoor dining

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 NZ$530
includes taxes & fees
12 July - 13 July
Pittsburgh Pennsylvania house
Property grounds

Explore Pittsburgh from a Modern, Hip Bungalow

Explore Pittsburgh from a Modern, Hip Bungalow
North Side
9.6 out of 10, Exceptional, (69 reviews)
"The property is extremely pet friendly! The house was clean and had everything you could want to have a relaxing experience. Very close to downtown. Lovely backyard. You won't regret staying there."
United States
Gabriellia
The price is NZ$331
includes taxes & fees
15 July - 16 July
Explore Pittsburgh from a Modern, Hip Bungalow
Interior

1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area

1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area
Bloomfield
10.0 out of 10, Exceptional, (31 reviews)
"We enjoyed our stay in the Friendship area of Pittsburgh. The apartment was exactly as pictured and was very clean and within walking distance of Penn St. which made getting everywhere convenient!"
United States
Kimberly N.
The price is NZ$314
includes taxes & fees
19 July - 20 July
1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area
A modern kitchen with a brick wall, wooden flooring, and a dining area with a table and chairs.

Brand New ★ Prime Location ★ Exposed Brick Beauty!

Brand New ★ Prime Location ★ Exposed Brick Beauty!
Lawrenceville
10.0 out of 10, Exceptional, (25 reviews)
"This place was great for our family of four. Walkable to many restaurants and shops. It was a quick drive to various attractions and areas of Pittsburgh. Of all the areas we visited, we liked Lawrenceville the best. Highly recommend this property for location, cleanliness, and easy check in. "
United States
Johanna M.
The price is NZ$458
includes taxes & fees
12 July - 13 July
Brand New ★ Prime Location ★ Exposed Brick Beauty!
Interior

★ HostWise Stays ★ 4 Blocks From UPMC Children's

★ HostWise Stays ★ 4 Blocks From UPMC Children's
Lawrenceville
10.0 out of 10, Exceptional, (14 reviews)
"The property was very clean and had all the amenities that made our Pittsburgh visit enjoyable. We enjoyed the location because it was it easy to get where we wanted to go. We would stay here again."
United States
Natalie D.
The price is NZ$411
includes taxes & fees
5 Aug - 6 Aug
★ HostWise Stays ★ 4 Blocks From UPMC Children's
TV

The Light Room

The Light Room
McKeesport
8.8 out of 10, Excellent, (13 reviews)
"Loved it here "
United States
Ciara S.
The price is NZ$349
includes taxes & fees
13 July - 14 July
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

Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent
"We have stayed at several Drury hotels across the US, and this one maintains the high standards of the chain. Clean, friendly staff, good breakfast/evening snacks. Loved the downtown location - very convenient to walk in the area - and a beautiful hotel building. Highly recommend!"
Shelley 1-night trip
Posted 6 hours ago
Drury Plaza Hotel Pittsburgh Downtown

Find out more about South Side

South Side Holiday Homes information

Number of reviews
182
Accommodation
736 Holiday Homes
Lowest Price
NZ$257
Highest Price
NZ$942

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