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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for South Side vacation rentals

A modern kitchen with a stainless steel refrigerator, granite countertop, and bar stools.

1. 2 Mi to Market Sq! Row House w/ Dedicated Office

2 Mi to Market Sq! Row House w/ Dedicated Office
3.5 star property
South Side Slopes
10.0 out of 10, Exceptional, (1 review)
"Great house! Feels brand new."
United States
Vincent
$344 nightly
The price is $392
Sep 15 - Sep 16
Total with taxes and fees
2 Mi to Market Sq! Row House w/ Dedicated Office
A modern living room with a sectional sofa, a dark coffee table, and a world map on the wall.

2. Iron City of South Side Flats Charming 2-bedroom Unit

Iron City of South Side Flats Charming 2-bedroom Unit
South Side Flats
9.8 out of 10, Exceptional, (10 reviews)
"Minus parking great stay will be back "
United States
Yolanda D.
$227 nightly
The price is $256
Sep 21 - Sep 22
Total with taxes and fees
Iron 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.

3. 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, (4 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
Sep 8 - Sep 9
Total with taxes and fees
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

4. 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.
$245 nightly
The price is $277
Sep 21 - Sep 22
Total with taxes and fees
Steel City of South Side Flats Charming 2-Bedroom Unit
A modern kitchen with a stainless steel refrigerator, granite countertop, and bar stools.

5. 2 Mi to Market Sq! Row House w/ Dedicated Office

2 Mi to Market Sq! Row House w/ Dedicated Office
South Side Slopes
10.0 out of 10, Exceptional, (2 reviews)
"I was there forvsurgery and the property was perfect for convalesing."
United States
Michael V.
$349 nightly
The price is $395
Sep 15 - Sep 16
Total with taxes and fees
2 Mi to Market Sq! Row House w/ Dedicated Office
A modern kitchen with a dining area, featuring a black stove, white cabinets, and a dining table with chairs.

6. M&J - 2615 Jane · Colorful Southside gem! Off-street parking!

M&J - 2615 Jane · Colorful Southside gem! Off-street parking!
South Side Flats
10.0 out of 10, Exceptional, (1 review)
"Was very nice and perfect for what we needed. Very closr to the GAP trail! "
United States
Hockey M.
$178 nightly
The price is $201
Sep 7 - Sep 8
Total with taxes and fees
M&J - 2615 Jane · Colorful Southside gem! Off-street parking!
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
10.0 out of 10, Exceptional, (1 review)
"Very nice place perfect for my needs."
United States
John
$255 nightly
The price is $289
Sep 7 - Sep 8
Total with taxes and fees
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with wicker chairs and a round table.

8. 2615 Jane Down - Southside

2615 Jane Down - Southside
South Side Flats
8.6 out of 10, Excellent, (4 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
Sep 8 - Sep 9
Total with taxes and fees
2615 Jane Down - Southside
An outdoor deck with a fire feature, seating, and a view of the city at night.

9. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
9.8 out of 10, Exceptional, (8 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.
$389 nightly
The price is $441
Sep 8 - Sep 9
Total with taxes and fees
City Skyline - Outside decks - Contemporary
A hallway with wooden doors leading to a bedroom with a bed and a ceiling fan.

10. 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 9 - Sep 10
Total with taxes and fees
Cozy Loft Studio in a Triplex, near SouthSideWorks
A living room with a grey sofa, a wooden coffee table, a world map on the wall, a television, and a door leading to another room.

11. Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi

Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi
South Side Slopes
$158 nightly
The price is $170
Sep 14 - Sep 15
Total with taxes and fees
Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi
A dining area with a table and chairs, a kitchen with cabinets and a stove, and a colorful cityscape painting on the wall.

12. 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 21 - Sep 22
Total with taxes and fees
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
A kitchen with wooden cabinets, a dining table with a floral tablecloth, and a glass of wine.

13. 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.
$293 nightly
The price is $320
Sep 19 - Sep 20
Total with taxes and fees
Carey Way Quarters – Stylish 3-Bedroom Loft!
A living room with a sofa, a flat-screen TV, and a kitchen area with wooden cabinets and a refrigerator.

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

Cozy South Side Retreat | Free Parking | Fast WiFi
South Side Slopes
$183 nightly
The price is $198
Sep 17 - Sep 18
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.

15. 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.
$371 nightly
The price is $420
Sep 8 - Sep 9
Total with taxes and fees
Cozy Centralized 3bd 2bath House w/ Free Parking
A row of brick townhouses with front porches, a small garden, and a visible mailbox.

16. 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
A neatly made bed with a unique towel arrangement, a headboard, and a decorative wall piece.

17. *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.
$284 nightly
The price is $321
Sep 7 - Sep 8
Total with taxes and fees
*Historic Gem* Heart of Southside-Sleeps 10
A modern kitchen with grey cabinets, a stainless steel dishwasher, a microwave, and wooden shelves with decorative items.

18. 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.
$231 nightly
The price is $256
Sep 6 - Sep 7
Total with taxes and fees
Industrial Chic Studio-Modern Comfort in the Burgh
An outdoor dining area with a wooden table and black chairs, surrounded by string lights and a white pergola.

19. 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.
$296 nightly
The price is $319
Sep 21 - Sep 22
Total with taxes and fees
Pittsburgh Pennsylvania house
A living room with a sofa, a flat-screen TV, and a kitchen area with wooden cabinets and a refrigerator.

20. Spacious 2BR South Side Retreat | Free Parking | Fast WiFi

Spacious 2BR South Side Retreat | Free Parking | Fast WiFi
South Side Slopes
Spacious 2BR South Side Retreat | Free Parking | Fast WiFi
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

La Quinta Inn by Wyndham Pittsburgh Airport

La Quinta Inn by Wyndham Pittsburgh Airport

8/10 Good
"Solid"
Jonathan 1-night trip
Posted 6 hours ago
La Quinta Inn by Wyndham Pittsburgh Airport

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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