South Side Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for South Side vacation homes
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk EverywhereSouth Side Flats
10.0 out of 10, Exceptional, (1 review)
"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.
The price is CA $121
CA $291 total
includes taxes & fees
Apr 13 - Apr 14
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!South Side Flats
8.0 out of 10, Very good, (11 reviews)
"Home was very comfy children enjoyed there stay I was able to relax and feel comfortable stay I would definitely book again."
bonita f.
The price is CA $59
CA $337 total
includes taxes & fees
Apr 13 - Apr 14
King Bed | Free Parking | Arcade | Fire Pit
King Bed | Free Parking | Arcade | Fire PitSouth Side Flats
9.8 out of 10, Exceptional, (26 reviews)
"Beautiful, spacious home, perfect for hosting our Friendsgiving! Love the backyard space. "
Lia L.
❤️Cozy Townhome on Carey with Private Deck Space ❤️
❤️Cozy Townhome on Carey with Private Deck Space ❤️Pittsburgh
8.2 out of 10, Very good, (36 reviews)
"Great location near the local nightlife"
Andrew M.
The price is CA $59
CA $338 total
includes taxes & fees
Apr 14 - Apr 15
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban LodgeAllentown
The price is CA $111
CA $368 total
includes taxes & fees
Apr 13 - Apr 14
Iron City of South Side Flats Charming 2-bedroom Unit
Iron City of South Side Flats Charming 2-bedroom UnitSouth Side Flats
The price is CA $142
CA $390 total
includes taxes & fees
Apr 13 - Apr 14
Steel City of South Side Flats Charming 2-Bedroom Unit
Steel City of South Side Flats Charming 2-Bedroom UnitSouth 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."
Heather B.
The price is CA $142
CA $388 total
includes taxes & fees
Apr 12 - Apr 13
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)
"My family and I had an excellent stay. The home was very nice, the host was very helpful, and the view was incredible! If you are looking for a rental that is close to everything but gives you the opportunity to get away from the busy city for some relaxation, this is your place."
Jason M.
The price is CA $443
CA $931 total
includes taxes & fees
Apr 9 - Apr 10
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top South Side Hotel Reviews
Hyatt Place Pittsburgh-North Shore
10/10 Excellent
Find out more about South Side
South Side Vacation Homes information
Number of reviews | 145 |
|---|---|
Accommodation | 663 Vacation Homes |
Lowest Price | CA $259 |
Highest Price | CA $1,295 |
Explore a world of travel with Expedia
- 5 Star Hotels in Arlington
- 5 Star Hotels in Knoxville
- 5 Star Hotels in St. Clair
- Hotels near Acrisure Stadium
- B&B in Allegheny County
- Cabin Rentals in Allegheny County
- Inns in Allegheny County
- Beach Hotel Hotels in Allentown
- Boutique Hotels in Allentown
- Golf Hotels in Allentown
- Historic Hotels in Allentown
- Hotels with Bar in Allentown
- Hotels with Hot Tubs in Allentown
- Hotels with Kitchenettes in Allentown
- Hotels with smoking rooms in Allentown
- Pet-Friendly Hotels in Allentown
- Spa Hotels in Allentown
- Waterpark Hotels in Allentown
- Allentown Hotels
- Hotel Wedding Venues Hotels in Arlington
- Bluff Hotels
- Crawford-Roberts Hotels
- Family Hotels in Allegheny County
- Golf Hotels in Allegheny County
- Historic Hotels in Allegheny County
- Hotels with Free Airport Shuttle in Allegheny County
- Hotels with Free Breakfast in Allegheny County
- Hotels with Hot Tubs in Allegheny County
- Luxury Hotels in Allegheny County
- Pet-Friendly Hotels in Allegheny County
- Ski Hotels in Allegheny County
- Spa Hotels in Allegheny County
- Allegheny County Hotels
- Downtown Pittsburgh Hotels
- Hotels near Duquesne University
- Hotels near First Avenue Station
- Apartments in Gateway Station
- Inns in Gateway Station
- Hotels with Hot Tubs in Knoxville
- Hotels with an Indoor Pool in Knoxville
- Hotels with Kitchenettes in Knoxville
- Pet-Friendly Hotels in Knoxville
- Knoxville Hotels
- Golf Hotels in Mount Oliver
- Luxury Hotels in Mount Oliver
- Mount Oliver Hotels
- Hotels near PNC Park
- Hotels near PPG Paints Arena
- Apartments in Palm Garden Station
- Farmstay in Pittsburgh
- Aparthotels in Pittsburgh
- B&B in Pittsburgh
- Capsule Hotels in Pittsburgh
- Castles in Pittsburgh
- Chalets in Pittsburgh
- Condo Rentals in Pittsburgh
- Cottages in Pittsburgh
- Country Houses in Pittsburgh
- Cruise Ships in Pittsburgh
- Guest Houses in Pittsburgh
- Holiday Park Resorts in Pittsburgh
- Hostels in Pittsburgh
- Cheap Hotels in Pittsburgh
- Pet-Friendly Hotels in Pittsburgh
- Pittsburgh Hotels
- Houseboats in Pittsburgh
- Inns in Pittsburgh
- Lodges in Pittsburgh
- Motels in Pittsburgh
- Ranches in Pittsburgh
- Resorts in Pittsburgh
- B&B in Pittsburgh Station
- Townhomes in Pittsburgh
- Treehouses in Pittsburgh
- Hotels near Rex Theater
- South Oakland Hotels
- Cheap Hotels in South Side Flats
- Hotels with Early Check-in in South Side Flats
- Hotels with Waterslides in South Side Flats
- Pet-Friendly Hotels in South Side Flats
- Spa Hotels in South Side Flats
- South Side Flats Hotels
- Hotels with Bar in South Side Slopes
- Hotels with smoking rooms in South Side Slopes
- Romantic Hotels in South Side Slopes
- Waterpark Hotels in South Side Slopes
- South Side Slopes Hotels
- St. Clair Hotels
- Terrace Village Hotels
- Condo Rentals in Westfield Station
- Aparthotels in Wood Street Station