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

South Side Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for South Side vacation rentals

A modern living room with a sofa, a coffee table, and a fireplace.

1. Spacious 3BR South Side Stay. Near Downtown Pittsburgh

Spacious 3BR South Side Stay. Near Downtown Pittsburgh
South Side Slopes
$239 nightly
The price is $271
Nov 17 - Nov 18
Total with taxes and fees
Spacious 3BR South Side Stay. Near Downtown Pittsburgh
A dining area with a brick wall, wicker furniture, a round table with a white vase, and a potted plant.

2. 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.
$173 nightly
The price is $196
Nov 17 - Nov 18
Total with taxes and fees
2615 Jane Down - Southside
A rustic bar area with wooden walls, two stools, a barrel, and a hanging light fixture.

3. 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.
The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!
A gated residential area with brick buildings and a concrete driveway.

4. 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, (14 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.
$228 nightly
The price is $258
Nov 16 - Nov 17
Total with taxes and fees
Iron City of South Side Flats Charming 2-bedroom Unit
A gated residential area with brick buildings and a concrete driveway.

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.
$236 nightly
The price is $267
Nov 17 - Nov 18
Total with taxes and fees
Steel City of South Side Flats Charming 2-Bedroom Unit
A modern living room with a fireplace, a television, a ceiling fan, and a kitchen in the background.

6. Your Pittsburgh Home Base. 3BR for Families & Groups

Your Pittsburgh Home Base. 3BR for Families & Groups
South Side Slopes
8.0 out of 10, Very good, (1 review)
"Every thing was great"
United States
Taibou C.
$247 nightly
The price is $281
Nov 16 - Nov 17
Total with taxes and fees
Your Pittsburgh Home Base. 3BR for Families & Groups
A modern kitchen with stainless steel appliances, a dining area with a table and chairs, and a hallway leading to the kitchen.

7. 3bd 2bath House + Free Parking

3bd 2bath House + 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.
$324 nightly
The price is $368
Nov 18 - Nov 19
Total with taxes and fees
3bd 2bath House + Free Parking
A dining area with a round table, white chairs, a hanging light fixture, a radiator, and a colorful cityscape painting on the wall.

8. 3-bedroom house in Southside Flats neighborhood of Pittsburgh.

3-bedroom house in Southside Flats neighborhood of Pittsburgh.
South Side Flats
8.0 out of 10, Very good, (3 reviews)
"Place was close to everything ee need the beds and kitchen was clean and the host was very helpful and the check in process was quick and easy"
United States
Alex C.
$211 nightly
The price is $239
Nov 17 - Nov 18
Total with taxes and fees
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
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.
$124 nightly
The price is $141
Nov 16 - Nov 17
Total with taxes and fees
Cozy&Modern 2Bdr Apt PIttsburgh
An outdoor dining area with a wooden table and black chairs, surrounded by string lights and a white pergola.

10. 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.
$233 nightly
The price is $248
Nov 16 - Nov 17
Total with taxes and fees
Pittsburgh Pennsylvania house
An outdoor seating area with Adirondack chairs, a fire pit, and a wooden lattice backdrop.

11. Sleeps 10 · Walk to Carson St · BBQ & Fire Pit

Sleeps 10 · Walk to Carson St · BBQ & Fire Pit
South Side Flats
$360 nightly
The price is $381
Nov 16 - Nov 17
Total with taxes and fees
Sleeps 10 · Walk to Carson St · BBQ & Fire Pit
A hot tub with a control panel, set against a green wall with snowflake decorations.

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

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Allentown
9.8 out of 10, Exceptional, (6 reviews)
"Very nice place perfect for my needs."
United States
John
$265 nightly
The price is $301
Nov 16 - Nov 17
Total with taxes and fees
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
A modern kitchen with white cabinets, stainless steel appliances, and a wooden countertop.

13. Pittsburgh South Side, 6BR Group Stay, 3 Baths, Sleeps 18

Pittsburgh South Side, 6BR Group Stay, 3 Baths, Sleeps 18
South Side Slopes
$462 nightly
The price is $525
Nov 16 - Nov 17
Total with taxes and fees
Pittsburgh South Side, 6BR Group Stay, 3 Baths, Sleeps 18
A hallway with wooden doors leading to a bedroom with a bed and a ceiling fan.

14. 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.
$135 nightly
The price is $153
Nov 17 - Nov 18
Total with taxes and fees
Cozy Loft Studio in a Triplex, near SouthSideWorks
An outdoor deck with a fire feature, seating, and a view of the city at night.

15. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
10.0 out of 10, Exceptional, (12 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.
$396 nightly
The price is $450
Nov 16 - Nov 17
Total with taxes and fees
City Skyline - Outside decks - Contemporary
A cozy outdoor seating area with a fire feature, wooden shelves with plants, and a brick wall with ivy.

16. King Bed | Garage Door Patio | Free Parking

King Bed | Garage Door Patio | Free Parking
South Side Flats
9.6 out of 10, Exceptional, (33 reviews)
"Great stay ! "
United States
Vidal R.
$444 nightly
The price is $446
Dec 2 - Dec 3
Total with taxes and fees
King Bed | Garage Door Patio | Free Parking
A stone wall, a wooden bench, and a table with decorative pillows and plants.

17. 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, (7 reviews)
"Great stay! Rooms were comfortable and very clean. "
United States
Anonymous traveler
$313 nightly
The price is $355
Nov 16 - Nov 17
Total with taxes and fees
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
A hallway with wooden flooring, a brick wall, and a radiator.

18. *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.
$273 nightly
The price is $310
Nov 17 - Nov 18
Total with taxes and fees
*Historic Gem* Heart of Southside-Sleeps 10
Interior

19. 4 Bedroom Beauty Spacious Home in Southside

4 Bedroom Beauty Spacious Home in Southside
South Side Flats
9.0 out of 10, Wonderful, (2 reviews)
"Very convenient location. "
United States
Rachel S.
$306 nightly
The price is $332
Nov 28 - Nov 29
Total with taxes and fees
4 Bedroom Beauty Spacious Home in Southside
An outdoor patio with a dining table, chairs, and an umbrella.

20. 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.
$525 nightly
The price is $595
Nov 16 - Nov 17
Total with taxes and fees
Central 5BD Getaway - Spacious Home w/ BBQ
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

Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent
"We had a great 2 night stay at the Drury! The room was clean and the bed was incredibly comfortable. The hot breakfasts and the food/drinks in the evening are an amazing value. The staff were all pleasant and helpful. The location was prefect for us to walk over to see a concert at the Wylie. Highly recommend!"
Nicole 2-night trip
Posted 2 hours ago
Drury Plaza Hotel 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 $113 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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