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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for South Side vacation rentals

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.

1. 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)
"Centrally located to lots of fun things to do and see. Great value. We would 100% stay here again next time we visit Pittsburgh. Street parking can be a little challenging but we were able to find spots within 2 blocks of the apartment."
United States
Joe A.
$266 nightly
The price is $290
Oct 11 - Oct 12
Total with taxes and fees
Carey Way Quarters-Stylish 3BR Loft-Prime Location
A living room with a fireplace, a television, and a dining area with a table and chairs.

2. 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 7 - Oct 8
Total with taxes and fees
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
A neatly made bed with a unique towel arrangement, a headboard, and a decorative wall piece.

3. *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.
$283 nightly
The price is $320
Oct 7 - Oct 8
Total with taxes and fees
*Historic Gem* Heart of Southside-Sleeps 10
A dining area with a round table, white chairs, a hanging light fixture, a radiator, and a colorful cityscape painting on the wall.

4. 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
Oct 20 - Oct 21
Total with taxes and fees
3-bedroom house in Southside Flats neighborhood of Pittsburgh.
A row of brick townhouses with front porches, a small garden, and a visible mailbox.

5. 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)
"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.
$442 nightly
The price is $500
Oct 7 - Oct 8
Total with taxes and fees
Central 5BD Getaway - Spacious Home w/ BBQ
A modern living room with a sectional sofa, a dark coffee table, and a world map on the wall.

6. 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.
$252 nightly
The price is $285
Oct 7 - Oct 8
Total with taxes and fees
Iron City of South Side Flats Charming 2-bedroom Unit
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

7. 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.
$211 nightly
The price is $230
Oct 11 - Oct 12
Total with taxes and fees
Carey Way Quarters – Modern 2BR Near Carson Street
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.
$254 nightly
The price is $287
Oct 7 - Oct 8
Total with taxes and fees
Steel City of South Side Flats Charming 2-Bedroom Unit
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with wicker chairs and a round table.

9. 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.
$171 nightly
The price is $193
Oct 7 - Oct 8
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.

10. 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.
$359 nightly
The price is $406
Oct 7 - Oct 8
Total with taxes and fees
City Skyline - Outside decks - Contemporary
A wooden deck with potted plants and a hanging fern.

11. 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.
$594 nightly
The price is $672
Oct 14 - Oct 15
Total with taxes and fees
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
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.
$389 nightly
The price is $440
Oct 20 - Oct 21
Total with taxes and fees
Cozy Centralized 3bd 2bath House w/ Free Parking
A backyard with a fire pit, a white chair, a colorful wall, and a wooden fence.

13. 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.
$693 nightly
The price is $699
Oct 11 - Oct 12
Total with taxes and fees
Pittsburgh House with Hot Tub, Patio & Free Parking!
A city skyline with a view of various buildings, including a prominent UPMC building.

14. 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
$375 nightly
The price is $425
Oct 12 - Oct 13
Total with taxes and fees
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
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
9.4 out of 10, Exceptional, (3 reviews)
"Very nice place perfect for my needs."
United States
John
$256 nightly
The price is $290
Oct 13 - Oct 14
Total with taxes and fees
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
A modern kitchen with white cabinets, stainless steel appliances, and a central island with a basket of decorative items.

16. 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
An outdoor dining area with a wooden table and black chairs, surrounded by string lights and a white pergola.

17. 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.
$242 nightly
The price is $257
Nov 3 - Nov 4
Total with taxes and fees
Pittsburgh Pennsylvania house
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.
$298 nightly
The price is $332
Oct 11 - Oct 12
Total with taxes and fees
Industrial Chic Studio-Modern Comfort in the Burgh
A historic building with a large arched entrance, multiple windows, and a clock tower.

19. Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian
4.0 star property
Downtown Pittsburgh
8.8 out of 10, Excellent, (281 reviews)
"Great stay"
United States
Brandon
$189 nightly
The price is $215
Oct 14 - Oct 15
Total with taxes and fees
Placemakr Downtown Pittsburgh at The Pennsylvanian
A modern kitchen with a cityscape view, a brick accent wall, and a small island with seating.

20. Charming 1-Bedroom Apartment in Lovely Pittsburgh With AC

Charming 1-Bedroom Apartment in Lovely Pittsburgh With AC
Bluff
10.0 out of 10, Exceptional, (16 reviews)
"Great location!"
United States
Amanuel A
$157 nightly
The price is $178
Oct 21 - Oct 22
Total with taxes and fees
Charming 1-Bedroom Apartment in Lovely Pittsburgh With AC
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

DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

10/10 Excellent
"Such a lovely hotel. So close to everything. Rooms were spotless, staff were friendly, parking was abundant, and always felt safe as mother traveling with small children. When we go back to Pittsburgh this is where we will stay."
GINA 2-night trip
Posted 2 hours ago
DoubleTree by Hilton Pittsburgh - Green Tree

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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