A park with autumn trees, a bridge, and a building labeled UPMC in the background.

South Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for South Side vacation rentals

A modern living room with a sectional sofa, a dark coffee table, and a world map on the wall.

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)
"Excellent property. Very convenient having on-site parking. Super clean, cozy, comfortable and well located. Will stay again this upcoming weekend!"
United States
Manuel M.
$227 nightly
The price is $256
Sep 29 - Sep 30
Total with taxes and fees
Iron 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.

2. 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)
"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."
United States
Kyle S.
$217 nightly
The price is $245
Sep 30 - Oct 1
Total with taxes and fees
3-bedroom house in Southside Flats neighborhood of Pittsburgh.

3. 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, (4 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."
United States
Heather B.
$243 nightly
The price is $275
Oct 6 - Oct 7
Total with taxes and fees
Steel City of South Side Flats Charming 2-Bedroom Unit
A kitchen with wooden cabinets, a dining table with a floral tablecloth, and a glass of wine.

4. Carey Way Quarters – Stylish 3-Bedroom Loft!

Carey Way Quarters – Stylish 3-Bedroom Loft!
South Side Flats
9.0 out of 10, Wonderful, (4 reviews)
"Our stay was as advertised!Thanks"
Canada
Kirk h.
$217 nightly
The price is $235
Oct 3 - Oct 4
Total with taxes and fees
Carey Way Quarters – Stylish 3-Bedroom Loft!
A living room with a fireplace, a television, and a dining area with a table and chairs.

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

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
South Side Flats
9.6 out of 10, Exceptional, (5 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.
$181 nightly
The price is $205
Oct 14 - Oct 15
Total with taxes and fees
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
An outdoor deck with a fire feature, seating, and a view of the city at night.

6. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
9.8 out of 10, Exceptional, (9 reviews)
"House was perfect for our small gathering of family and friends. We lived out on the decks where the view is spectacular. Host could not have been better. Thanks for a perfect stay!"
United States
Glen C.
$358 nightly
The price is $405
Sep 23 - Sep 24
Total with taxes and fees
City Skyline - Outside decks - Contemporary
A modern kitchen with white cabinets, a stainless steel dishwasher, a microwave, and a black countertop.

7. 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)
"Very nice place perfect for my needs."
United States
John
$254 nightly
The price is $288
Sep 23 - Sep 24
Total with taxes and fees
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with bar stools.

8. Cozy South Side Retreat | Free Parking | Fast WiFi

Cozy South Side Retreat | Free Parking | Fast WiFi
South Side Slopes
$203 nightly
The price is $221
Oct 2 - Oct 3
Total with taxes and fees
Cozy South Side Retreat | Free Parking | Fast WiFi
A dining area with a table and chairs, a kitchen in the background, and a modern light fixture.

9. 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.
$530 nightly
The price is $600
Sep 23 - Sep 24
Total with taxes and fees
Cozy Centralized 3bd 2bath House w/ Free Parking
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

10. Carey Way Quarters – Modern 2BR Near Carson Street

Carey Way Quarters – Modern 2BR Near Carson Street
South Side Flats
9.0 out of 10, Wonderful, (14 reviews)
"Great location and property"
United States
Corey E.
$263 nightly
The price is $289
Sep 25 - Sep 26
Total with taxes and fees
Carey Way Quarters – Modern 2BR Near Carson Street
A modern kitchen with grey cabinets, a stainless steel dishwasher, a microwave, and wooden shelves with decorative items.

11. Industrial Chic Studio-Modern Comfort in the Burgh

Industrial Chic Studio-Modern Comfort in the Burgh
South Side Flats
9.8 out of 10, Exceptional, (8 reviews)
"Great place to stay. Easy access to bridges which then led us to Pitt to visit. Owner was very responsive to our questions. We'd stay here again!"
United States
Rich D.
$216 nightly
The price is $239
Oct 2 - Oct 3
Total with taxes and fees
Industrial Chic Studio-Modern Comfort in the Burgh
A neatly made bed with a unique towel arrangement, a headboard, and a decorative wall piece.

12. *Historic Gem* Heart of Southside-Sleeps 10

*Historic Gem* Heart of Southside-Sleeps 10
South Side Flats
9.0 out of 10, Wonderful, (32 reviews)
"The place exceeded my wildest expectations. I would highly recommend this hidden gem to anyone looking to stay on the South side"
United States
hans e.
$283 nightly
The price is $320
Sep 23 - Sep 24
Total with taxes and fees
*Historic Gem* Heart of Southside-Sleeps 10
A hallway with wooden doors leading to a bedroom with a bed and a ceiling fan.

13. Cozy Loft Studio in a Triplex, near SouthSideWorks

Cozy Loft Studio in a Triplex, near SouthSideWorks
South Side Flats
8.0 out of 10, Very good, (2 reviews)
"Great communication"
United States
Clay B.
$143 nightly
The price is $161
Sep 23 - Sep 24
Total with taxes and fees
Cozy Loft Studio in a Triplex, near SouthSideWorks
A row of brick townhouses with front porches, a small garden, and a visible mailbox.

14. 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)
"Stayed for a guys weekend with the family, everybody was very happy with the accommodations and the proximity to restaurants and such. Phil and Dotty were two of the most gracious responsive hosts I’ve ever had the pleasure of dealing with. Would def rent again if back in Pittsburgh"
United States
Sean O.
$407 nightly
The price is $461
Sep 23 - Sep 24
Total with taxes and fees
Central 5BD Getaway - Spacious Home w/ BBQ
An outdoor dining area with a wooden table and black chairs, surrounded by string lights and a white pergola.

15. 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.
$291 nightly
The price is $314
Oct 20 - Oct 21
Total with taxes and fees
Pittsburgh Pennsylvania house
A wooden deck with potted plants and a hanging fern.

16. 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)
"Fantastic property. Intriguing history. Great location."
United States
Kevin M.
$548 nightly
The price is $620
Oct 14 - Oct 15
Total with taxes and fees
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
A compact kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dishwasher.

17. Carey Way Quarters - Explorer's Dream Pad

Carey Way Quarters - Explorer's Dream Pad
South Side Flats
$182 nightly
The price is $200
Oct 2 - Oct 3
Total with taxes and fees
Carey Way Quarters - Explorer's Dream Pad
A backyard with a fire pit, a white chair, a colorful wall, and a wooden fence.

18. Pittsburgh House with Hot Tub, Patio & Free Parking!

Pittsburgh House with Hot Tub, Patio & Free Parking!
South Side Flats
10.0 out of 10, Exceptional, (8 reviews)
"I had an excellent stay at this property and would definitely stay here again. The home was comfortable and stylish. The bedding, towels, and linens were fresh, soft, and comfortable. The neighborhood was charming, walkable, and conveniently located in relation to restaurants and other attractions. The host was also very responsive to questions."
United States
Karin
$884 nightly
The price is $892
Oct 11 - Oct 12
Total with taxes and fees
Pittsburgh House with Hot Tub, Patio & Free Parking!
A modern kitchen with white cabinets, stainless steel appliances, and a central island with a basket of decorative items.

19. 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)
"This is such a cute house that is close to downtown. 10/10 would recommend this house. It was perfect for us!"
United States
Amanda R.
$611 nightly
The price is $691
Oct 11 - Oct 12
Total with taxes and fees
Clean and comfortable 3BR home in the South Side neighborhood
A modern kitchen with dark cabinets, stainless steel appliances, a central island with stools, and a chandelier.

20. King Bed | Free Parking | BBQ | Fire pit | Arcade

King Bed | Free Parking | BBQ | Fire pit | Arcade
South Side Flats
9.8 out of 10, Exceptional, (70 reviews)
"Great location and an amazing value"
United States
Tony J.
$952 nightly
The price is $960
Sep 25 - Sep 26
Total with taxes and fees
King Bed | Free Parking | BBQ | Fire pit | Arcade
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

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

8/10 Good
"Good location, fair service at checkin and no line, elevators were not too crowded and fast, decent gym, nice pool with a little jacuzzi next to it. Problem was housekeeping slamming on the doors at 9 Saturday morning. And we were there two days hoping to get a refresh on towels and coffee but no go."
Beth 2-night trip
Posted 2 hours ago
Wyndham Grand Pittsburgh Downtown

Find out more about South Side

Everything you need to know about South Side vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Side vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Side vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Side. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Side in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Side rentals

At Expedia, we put the best South Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Side vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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