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 compact kitchen with a microwave, sink, and dishwasher.

1. Bunkhouse - Budget Crash Pad - East Carson Street

Bunkhouse - Budget Crash Pad - East Carson Street
South Side Flats
$185 nightly
The price is $202
Nov 14 - Nov 15
Total with taxes and fees
Bunkhouse - Budget Crash Pad - East Carson Street
A living room with a sofa, a flat-screen TV, and a kitchen area with wooden cabinets and a refrigerator.

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

Spacious 2BR South Side Retreat | Free Parking | Fast WiFi
South Side Slopes
$190 nightly
The price is $204
Oct 26 - Oct 27
Total with taxes and fees
Spacious 2BR South Side Retreat | Free Parking | Fast WiFi
Two bottles of Drops laundry detergent and bleach additive on a shelf.

3. 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.
$172 nightly
The price is $194
Oct 27 - Oct 28
Total with taxes and fees
2615 Jane Down - Southside
A living room with a fireplace, a television, and a dining area with a table and chairs.

4. 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.
$183 nightly
The price is $207
Oct 26 - Oct 27
Total with taxes and fees
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with bar stools.

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

Cozy South Side Retreat | Free Parking | Fast WiFi
South Side Slopes
$158 nightly
The price is $170
Oct 26 - Oct 27
Total with taxes and fees
Cozy South Side Retreat | Free Parking | Fast WiFi
A bedroom with a bed, bedside table, dresser, and a large rug.

6. The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!

The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!
South Side Flats
7.0 out of 10, Good, (2 reviews)
"It was a nice and beautiful place "
United States
Alyssa B.
$131 nightly
The price is $142
Nov 7 - Nov 8
Total with taxes and fees
The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!
A modern living room with a sectional sofa, a dark coffee table, and a world map on the wall.

7. 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.
$246 nightly
The price is $278
Oct 27 - Oct 28
Total with taxes and fees
Iron City of South Side Flats Charming 2-bedroom Unit
Private kitchen

8. 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.
$247 nightly
The price is $279
Oct 27 - Oct 28
Total with taxes and fees
Steel City of South Side Flats Charming 2-Bedroom Unit
A modern kitchen with a brick wall, white bar stools, and a dining area with a grey sofa.

9. 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 26 - Oct 27
Total with taxes and fees
Cozy&Modern 2Bdr Apt PIttsburgh
A dining area with a round table, white chairs, a hanging light fixture, a radiator, and a colorful cityscape painting on the wall.

10. 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 27 - Oct 28
Total with taxes and fees
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

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

Carey Way Quarters – Modern 2BR Near Carson Street
South Side Flats
9.2 out of 10, Wonderful, (15 reviews)
"Great location and property"
United States
Corey E.
$178 nightly
The price is $193
Nov 7 - Nov 8
Total with taxes and fees
Carey Way Quarters – Modern 2BR Near Carson Street
A dining area with a table and chairs, a potted plant, and a wall-mounted light fixture.

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.
$359 nightly
The price is $406
Oct 27 - Oct 28
Total with taxes and fees
Cozy Centralized 3bd 2bath House w/ Free Parking
A room with a television mounted on the wall, a wicker chair with blue cushions, a wooden cabinet with drawers, and a wall-mounted lamp.

13. 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.
$263 nightly
The price is $282
Nov 3 - Nov 4
Total with taxes and fees
Pittsburgh Pennsylvania house
An outdoor deck with a fire feature, seating, and a view of the city at night.

14. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay in this beautiful home! The host was super responsive and helpful. The home is spacious and well kept with amazing views of the city. The cherry on top was the driveway/parking area that accommodated our five vehicles. Great choice for our family get together!"
United States
Mary H.
$364 nightly
The price is $411
Oct 26 - Oct 27
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.

15. Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Allentown
9.6 out of 10, Exceptional, (4 reviews)
"Very nice place perfect for my needs."
United States
John
$283 nightly
The price is $320
Nov 2 - Nov 3
Total with taxes and fees
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
A compact kitchen with white cabinets, a stove, a sink, and wooden stools.

16. 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
A modern kitchen with grey cabinets, a stainless steel dishwasher, a microwave, and wooden shelves with decorative items.

17. 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.
$178 nightly
The price is $196
Nov 1 - Nov 2
Total with taxes and fees
Industrial Chic Studio-Modern Comfort in the Burgh
A row of brick townhouses with front porches, a small garden, and a visible mailbox.

18. 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.
$448 nightly
The price is $506
Oct 26 - Oct 27
Total with taxes and fees
Central 5BD Getaway - Spacious Home w/ BBQ
A neatly made bed with a unique towel arrangement, a headboard, and a decorative wall piece.

19. *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.
$289 nightly
The price is $327
Oct 26 - Oct 27
Total with taxes and fees
*Historic Gem* Heart of Southside-Sleeps 10
A city skyline with prominent buildings and a river.

20. 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
$463 nightly
The price is $523
Nov 2 - Nov 3
Total with taxes and fees
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
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

Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG

Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG

8/10 Good
"Room was fine and met our needs. Breakfast and fitness center are good. Desk staff were very friendly and helpful. The breakfast staff person was not very friendly and did not seem to enjoy her job. She also smoked at the front entrance while on break. Not a good look for someone handling food."
Mark 2-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG

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 $122 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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