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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for South Side vacation rentals

A historic building with a large arched entrance, multiple windows, and a clock tower.

1. Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian
4.0 star property
Downtown Pittsburgh
8.8 out of 10, Excellent, (305 reviews)
"Great stay"
United States
Brandon
$151 nightly
The price is $172
Nov 3 - Nov 4
Total with taxes and fees
Placemakr Downtown Pittsburgh at The Pennsylvanian
A hallway with a double door leading to an outdoor area, a staircase, and a view of a brick building.

2. 1 Mi to Dtwn! New Pet-friendly Condo in Pittsburgh

1 Mi to Dtwn! New Pet-friendly Condo in Pittsburgh
3.5 star property
Crawford-Roberts
8.0 out of 10, Very good, (2 reviews)
"The wifi instructions were not found but that was a minor inconvenience."
United States
Jim
$240 nightly
The price is $274
Oct 18 - Oct 19
Total with taxes and fees
1 Mi to Dtwn! New Pet-friendly Condo in Pittsburgh
A brick building with a large arched entrance labeled "STAYPGH".

3. Stay Pittsburgh

Stay Pittsburgh
2.0 star property
Downtown Pittsburgh
8.0 out of 10, Very good, (338 reviews)
"Easy to access the down town tour and public parking garage near by"
United States
Krishna
$137 nightly
The price is $156
Oct 18 - Oct 19
Total with taxes and fees
Stay Pittsburgh
A modern kitchen with white cabinets, a built-in oven, and a large window offering a city view.

4. CozySuites - William

CozySuites - William
4.0 star property
Downtown Pittsburgh
6.0 out of 10, (27 reviews)
"Great price and a reasonably comfortable room. Superb location."
United States
Andrew
$137 nightly
The price is $156
Oct 21 - Oct 22
Total with taxes and fees
CozySuites - William
A modern living room with a gray sofa, a glass table, and a view of a cityscape through large windows.

5. CozySuites - Press House

CozySuites - Press House
4.0 star property
Downtown Pittsburgh
5.0 out of 10, (19 reviews)
"Great stay"
United States
Gwen
$131 nightly
The price is $150
Oct 20 - Oct 21
Total with taxes and fees
CozySuites - Press House
A grand banquet hall with high ceilings, ornate columns, and a central stage. Tables are set for a formal event, with floral centerpieces and elegant table settings.

6. Abode Pittsburgh - Downtown Convention Center

Abode Pittsburgh - Downtown Convention Center
3.5 star property
Downtown Pittsburgh
7.6 out of 10, Good, (98 reviews)
$164 nightly
The price is $187
Oct 21 - Oct 22
Total with taxes and fees
Abode Pittsburgh - Downtown Convention Center
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

7. 424 Gold Way-Apt 402, 2 Bed/1Bath

424 Gold Way-Apt 402, 2 Bed/1Bath
3.5 star property
Oakland
9.2 out of 10, Wonderful, (13 reviews)
$189 nightly
The price is $215
Oct 21 - Oct 22
Total with taxes and fees
424 Gold Way-Apt 402, 2 Bed/1Bath
A modern interior with a polished floor, a grey sofa, and a white door with text.

8. Melwood Suites Unit 107 Studio

Melwood Suites Unit 107 Studio
2.0 star property
Oakland
9.4 out of 10, Exceptional, (49 reviews)
"Exceptionally clean, spacious, very comfortable!"
United States
Lisa
$169 nightly
The price is $192
Oct 19 - Oct 20
Total with taxes and fees
Melwood Suites Unit 107 Studio
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

9. 424 Gold Way-Apt. 303

424 Gold Way-Apt. 303
3.5 star property
Oakland
8.6 out of 10, Excellent, (17 reviews)
"I love this place great place to get away and be comfortable "
United States
Damon
$189 nightly
The price is $215
Oct 21 - Oct 22
Total with taxes and fees
424 Gold Way-Apt. 303
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

10. 424 Gold Way-Apt. 302

424 Gold Way-Apt. 302
3.5 star property
Oakland
9.8 out of 10, Exceptional, (24 reviews)
"Great location. Unit is spacious. Will stay there for our next visit!"
United States
Kai
$203 nightly
The price is $231
Oct 21 - Oct 22
Total with taxes and fees
424 Gold Way-Apt. 302
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

11. 424-Apt. 400

424-Apt. 400
3.5 star property
Oakland
8.0 out of 10, Very good, (8 reviews)
"Really great place to stay for the price. Spacious and airy, with exceptionally comfortable beds and pillows! Easy and free street parking, great location. Excellent stay."
United States
theresa
$261 nightly
The price is $298
Oct 21 - Oct 22
Total with taxes and fees
424-Apt. 400
A modern living room with a sofa, a coffee table, and a TV. There is a ceiling fan, a fireplace, and a window with curtains.

12. Dog-friendly Pittsburgh Home, 3 Mi to Downtown!

Dog-friendly Pittsburgh Home, 3 Mi to Downtown!
3.0 star property
Mount Washington
9.0 out of 10, Wonderful, (4 reviews)
"Perfect for our needs"
United States
Barbara
$387 nightly
The price is $441
Nov 3 - Nov 4
Total with taxes and fees
Dog-friendly Pittsburgh Home, 3 Mi to Downtown!
A building with a large window displaying a cityscape, a sign indicating 'MEIJU SOOIDS', and a brick facade.

13. 461 Melwood Suites Unit 101 2Bed/2Bath

461 Melwood Suites Unit 101 2Bed/2Bath
3.0 star property
Oakland
9.6 out of 10, Exceptional, (4 reviews)
"Very responsive, easy access, great value."
United States
Justin
$244 nightly
The price is $278
Oct 21 - Oct 22
Total with taxes and fees
461 Melwood Suites Unit 101 2Bed/2Bath
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

14. 424 Gold Way - Apt. 404 2Bed/1Bath

424 Gold Way - Apt. 404 2Bed/1Bath
3.5 star property
Oakland
9.2 out of 10, Wonderful, (17 reviews)
"Loved this hidden gem walkable to Pitts campus!"
United States
Jessica
$189 nightly
The price is $215
Oct 21 - Oct 22
Total with taxes and fees
424 Gold Way - Apt. 404 2Bed/1Bath
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

15. 424-Apt. 403

424-Apt. 403
3.5 star property
Oakland
9.6 out of 10, Exceptional, (37 reviews)
"Third time here and will come back!"
Singapore
Laurence
$163 nightly
The price is $186
Oct 21 - Oct 22
Total with taxes and fees
424-Apt. 403
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

16. 424-Apt. 405

424-Apt. 405
3.5 star property
Oakland
9.4 out of 10, Exceptional, (12 reviews)
"It was perfect!"
United States
Ninway
$177 nightly
The price is $202
Oct 26 - Oct 27
Total with taxes and fees
424-Apt. 405
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

17. 424-Apt 304

424-Apt 304
3.5 star property
Oakland
9.2 out of 10, Wonderful, (12 reviews)
"Love the location nicely done Will return "
United States
Lamont
$166 nightly
The price is $189
Oct 26 - Oct 27
Total with taxes and fees
424-Apt 304
A building with a large illuminated number '424' sign, a metal awning, and a brick facade.

18. 424-Apt. 406

424-Apt. 406
3.5 star property
Oakland
9.0 out of 10, Wonderful, (6 reviews)
"Awesome apartment in an ideal location. We loved this place. "
United States
Wilson
$189 nightly
The price is $215
Oct 18 - Oct 19
Total with taxes and fees
424-Apt. 406
A modern hotel interior with a polished floor, a sofa, and a bed in the background.

19. 461 Melwood Suites Unit 102 Studio

461 Melwood Suites Unit 102 Studio
2.0 star property
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"Property manage me were very responsive. We added one more night close to our stay because we realize our flight was arriving super early, so we reached out, problem solved. Also, we got good recommendations on what’s around the area to eat and local sight seeing places not promoted on the internet. Overall, best customer services all around"
United States
Steve
$295 nightly
The price is $336
Oct 19 - Oct 20
Total with taxes and fees
461 Melwood Suites Unit 102 Studio
A hotel room with a bed, a flat-screen TV mounted on the wall, a kitchenette with a refrigerator, and a small seating area with a sofa and a table.

20. Melwood Suites Unit 106 Studio

Melwood Suites Unit 106 Studio
2.0 star property
Oakland
9.6 out of 10, Exceptional, (4 reviews)
"Best stay ever! And I’ve been many places. "
United States
Malcolm
$229 nightly
The price is $261
Oct 18 - Oct 19
Total with taxes and fees
Melwood Suites Unit 106 Studio
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 Hotel & Suites Pittsburgh-South Side by IHG

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

8/10 Good
"pretty clean and ok location staff was very pleasant to work with and helpful"
Meredith 1-night trip
Posted 3 hours ago
Holiday Inn Express Hotel & Suites Pittsburgh-South Side 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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