Stay South Side

Stay South Side Short term rentals in Pittsburgh's Historic South Side. Stay with us and live like a local. Top quality amenities. Walk everywhere.

Check out this awesome event with and
04/08/2026

Check out this awesome event with and

We’ve been a Superhost for 9 years straight. We didn’t even cancel when four lucky groups booked our places for Pittsbur...
04/07/2026

We’ve been a Superhost for 9 years straight. We didn’t even cancel when four lucky groups booked our places for Pittsburgh’s NFL draft at super affordable rates!

Our newest place is now ready. The former Saint Peter’s rectory on Pittsburgh’s South Side. Book direct at www.staysouth...
10/03/2025

Our newest place is now ready. The former Saint Peter’s rectory on Pittsburgh’s South Side. Book direct at www.staysouthside.com. Let me know you saw this post and I will make you a deal.

These lovely ladies from Elizabeth Seton High School had a reunion at our Saint Casimir property this week!
10/02/2025

These lovely ladies from Elizabeth Seton High School had a reunion at our Saint Casimir property this week!

We found this bench at !
09/18/2025

We found this bench at !

Found under wood paneling at our new project…what does it all mean?
05/08/2025

Found under wood paneling at our new project…what does it all mean?

Another great review during graduation season!
05/08/2025

Another great review during graduation season!

Something new and exciting is coming soon near this intersection of the South Side!
03/27/2025

Something new and exciting is coming soon near this intersection of the South Side!

tea at all of our rentals this winter. Enjoy!
01/23/2025

tea at all of our rentals this winter. Enjoy!

Another great review for Stay South Side!
10/21/2024

Another great review for Stay South Side!

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