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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for South Side vacation rentals

A kitchen with wooden cabinets, a dining table with a floral tablecloth, and a glass of wine.

1. 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.
$247 nightly
The price is $268
Nov 6 - Nov 7
Total with taxes and fees
Carey Way Quarters – Stylish 3-Bedroom Loft!
A backyard with a fire pit, a white chair, a colorful wall, and a wooden fence.

2. 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)
"Perfect vibes for a small girls trip. Great location. Such a fun place, thanks for the small details!"
United States
Sara P.
$899 nightly
The price is $907
Nov 12 - Nov 13
Total with taxes and fees
Pittsburgh House with Hot Tub, Patio & Free Parking!
A modern living room with a sectional sofa, a dark coffee table, and a world map on the wall.

3. 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, (12 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.
$248 nightly
The price is $281
Oct 27 - Oct 28
Total with taxes and fees
Iron City of South Side Flats Charming 2-bedroom Unit
A neatly made bed with a unique towel arrangement, a headboard, and a decorative wall piece.

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

*Historic Gem* Heart of Southside-Sleeps 10
South Side Flats
8.8 out of 10, Excellent, (33 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.
$288 nightly
The price is $326
Oct 22 - Oct 23
Total with taxes and fees
*Historic Gem* Heart of Southside-Sleeps 10
Private kitchen

5. 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, (5 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.
$250 nightly
The price is $283
Oct 27 - Oct 28
Total with taxes and fees
Steel City of South Side Flats Charming 2-Bedroom Unit
A living room with a fireplace, a television, and a dining area with a table and chairs.

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

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
South Side Flats
9.8 out of 10, Exceptional, (6 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 26 - Oct 27
Total with taxes and fees
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
A modern kitchen with a brick wall, white bar stools, and a dining area with a grey sofa.

7. Cozy&Modern 2Bdr Apt PIttsburgh

Cozy&Modern 2Bdr Apt PIttsburgh
South Side Flats
10.0 out of 10, Exceptional, (20 reviews)
"Great location, very clean, and exactly as described. We had a wonderful stay and would definitely stay here again! "
United States
Abby S.
$136 nightly
The price is $154
Oct 22 - Oct 23
Total with taxes and fees
Cozy&Modern 2Bdr Apt PIttsburgh
A row of brick townhouses with front porches, a small garden, and a visible mailbox.

8. Central 5BD Getaway - Spacious Home w/ BBQ

Central 5BD Getaway - Spacious Home w/ BBQ
South Side Flats
10.0 out of 10, Exceptional, (12 reviews)
"Great host and property "
United States
Eric G.
Central 5BD Getaway - Spacious Home w/ BBQ
A dining area with a round table, white chairs, a hanging light fixture, a radiator, and a colorful cityscape painting on the wall.

9. 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.
$203 nightly
The price is $230
Oct 22 - Oct 23
Total with taxes and fees
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
A wooden deck with potted plants and a hanging fern.

10. 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.
$630 nightly
The price is $713
Oct 29 - Oct 30
Total with taxes and fees
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with wicker chairs and a round table.

11. 2615 Jane Down - Southside

2615 Jane Down - Southside
South Side Flats
8.8 out of 10, Excellent, (5 reviews)
"Very clean modern place in nice neighborhood. Location great for walking. Found a vegan restaurant less than two blocks away. "
United States
Bertha T.
$170 nightly
The price is $192
Oct 27 - Oct 28
Total with taxes and fees
2615 Jane Down - Southside
A living room with a green sofa, a glass coffee table, a TV mounted on the wall, and a sliding barn door.

12. 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.
$375 nightly
The price is $424
Nov 4 - Nov 5
Total with taxes and fees
Cozy Centralized 3bd 2bath House w/ Free Parking
A compact room with bunk beds, a small shelf unit, and a door leading to a storage area.

13. Bunkhouse - Budget Crash Pad - East Carson Street

Bunkhouse - Budget Crash Pad - East Carson Street
South Side Flats
$162 nightly
The price is $176
Nov 14 - Nov 15
Total with taxes and fees
Bunkhouse - Budget Crash Pad - East Carson Street
A modern kitchen with white cabinets, a stainless steel dishwasher, a microwave, and a black countertop.

14. 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
Oct 25 - Oct 26
Total with taxes and fees
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
A city skyline with a view of various buildings, including a prominent UPMC building.

15. 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, (6 reviews)
"Great stay! Rooms were comfortable and very clean. "
United States
Anonymous traveler
$370 nightly
The price is $419
Oct 27 - Oct 28
Total with taxes and fees
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
An outdoor dining area with a wooden table and black chairs, surrounded by string lights and a white pergola.

16. 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.
$248 nightly
The price is $264
Nov 10 - Nov 11
Total with taxes and fees
Pittsburgh Pennsylvania house
A modern kitchen with wooden cabinets, a microwave, and a stove. There is a dining area with a table and chairs, a TV mounted on the wall, and a potted plant.

17. Carey Way Quarters-Stylish 3BR Loft-Prime Location

Carey Way Quarters-Stylish 3BR Loft-Prime Location
South Side Flats
9.4 out of 10, Exceptional, (6 reviews)
"Good stay, easy check in, lovely location. "
United States
Carolee V.
$247 nightly
The price is $268
Nov 1 - Nov 2
Total with taxes and fees
Carey Way Quarters-Stylish 3BR Loft-Prime Location
A compact kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dishwasher.

18. Carey Way Quarters - Explorer's Dream Pad

Carey Way Quarters - Explorer's Dream Pad
South Side Flats
$162 nightly
The price is $178
Nov 13 - Nov 14
Total with taxes and fees
Carey Way Quarters - Explorer's Dream Pad
A modern kitchen with grey cabinets, a stainless steel dishwasher, a microwave, and wooden shelves with decorative items.

19. 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.
$184 nightly
The price is $203
Nov 1 - Nov 2
Total with taxes and fees
Industrial Chic Studio-Modern Comfort in the Burgh
A hallway with wooden doors leading to a bedroom with a bed and a ceiling fan.

20. 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
Nov 1 - Nov 2
Total with taxes and fees
Cozy Loft Studio in a Triplex, near SouthSideWorks
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

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

10/10 Excellent
"Excellent hotel! Close to everything. Had the coolest lobby with a typewriter that you could hand type fun notes!"
Melissa 3-night trip
Posted less than an hour ago
Joinery Hotel Pittsburgh, Curio Collection by Hilton

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 $127 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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