South Side Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in South Side

Exterior
Kasa South Side Pittsburgh

Kasa South Side Pittsburgh

4.0 star property
South Side Flats
8.0 out of 10, Very Good, (104)
"Clean great views hotel "
United States
Shomario
$203 nightly
The price is $231
Nov 25 - Nov 26
Total with taxes and fees
Kasa South Side Pittsburgh
Outdoor dining
Clean & Central Pittsburgh Retreat • Cozy + Highly Walkable!

Clean & Central Pittsburgh Retreat • Cozy + Highly Walkable!

South Side Flats
7.0 out of 10, Good, (4)
"Very well organized and clean. Host was quick to communicate and helpful."
United States
Noah S.
Clean & Central Pittsburgh Retreat • Cozy + Highly Walkable!
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Cozy&Modern 2Bdr Apt PIttsburgh

Cozy&Modern 2Bdr Apt PIttsburgh

2.0 star property
South Side Flats
10.0 out of 10, Exceptional, (8)
"Good location right of East Carson. Enjoyed our stay."
United States
Emma P.
Cozy&Modern 2Bdr Apt PIttsburgh
Apartment (0 Bedroom) | Front of property
Walkable Studio in the Heart of Pittsburgh!

Walkable Studio in the Heart of Pittsburgh!

3.0 star property
South Side Flats
2.0 out of 10, (1)
"A Complete Dump! Did not stay!"
United States
John
Walkable Studio in the Heart of Pittsburgh!
Front of property
Stay Pittsburgh

Stay Pittsburgh

2.0 star property
Downtown Pittsburgh
7.8 out of 10, Good, (207)
"Great location"
United States
Angela
$94 nightly
The price is $107
Dec 1 - Dec 2
Total with taxes and fees
Stay Pittsburgh
Exterior
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4.0 star property
Downtown Pittsburgh
7.6 out of 10, Good, (38)
"Staff was awesome so helpful and kind. Room was clean and had everything we needed."
United States
Tiffany
$133 nightly
The price is $152
Dec 1 - Dec 2
Total with taxes and fees
Placemakr Downtown Pittsburgh at The Pennsylvanian
Interior
Abode Pittsburgh - Downtown Convention Center

Abode Pittsburgh - Downtown Convention Center

3.5 star property
Downtown Pittsburgh
7.6 out of 10, Good, (86)
"Clean Room, Quiet, and Great location to Downtown Convention Center (7 min walk), Courteous Bldg. Staff, Excellent Communications and Instructions for Property Access. Tub and Stove-Top signs of wear, but nicely setup. Would stay again. A+++"
United States
Curtis E
$142 nightly
The price is $162
Nov 24 - Nov 25
Total with taxes and fees
Abode Pittsburgh - Downtown Convention Center
Studio, 1 Queen Bed with Sofa bed, Non Smoking, Kitchenette | Free WiFi
Melwood Suites Unit 107 Studio

Melwood Suites Unit 107 Studio

2.0 star property
Oakland
9.6 out of 10, Exceptional, (39)
"Spotless, amazing stay"
United States
Carlos
$133 nightly
The price is $152
Nov 23 - Nov 24
Total with taxes and fees
Melwood Suites Unit 107 Studio
Deluxe Apartment, 1 Bedroom, Non Smoking | Private kitchen | Full-size fridge, microwave, oven, stovetop
CozySuites - Press House

CozySuites - Press House

2.0 star property
Downtown Pittsburgh
3.6 out of 10, (5)
"Nice area in downtown Pittsburg PA. It was roomy. Furniture was cheap but we understand why. "
United States
Elliott
$151 nightly
The price is $172
Nov 23 - Nov 24
Total with taxes and fees
CozySuites - Press House
Apartment | 2 bedrooms
2 Bedroom Downtown Apt Clean and Safe

2 Bedroom Downtown Apt Clean and Safe

2.0 star property
Downtown Pittsburgh
10.0 out of 10, Exceptional, (1)
"I enjoyed the location very much. It was so easy to get to, everything was walking distance and the view was gorgeous. The rooms were tidy with comfortable furniture and smelled pleasant. I plan on trying to stay here anytime i am in the city. "
United States
Michael
$121 nightly
The price is $137
Nov 24 - Nov 25
Total with taxes and fees
2 Bedroom Downtown Apt Clean and Safe
Apartment | 1 bedroom
Cute Downtown APT Quick Safe Walk to PPG Arena

Cute Downtown APT Quick Safe Walk to PPG Arena

2.0 star property
Downtown Pittsburgh
$96 nightly
The price is $110
Dec 1 - Dec 2
Total with taxes and fees
Cute Downtown APT Quick Safe Walk to PPG Arena
Deluxe Apartment, 1 Queen Bed, Non Smoking | Private kitchen | Fridge, microwave, stovetop, dishwasher
CozySuites - William

CozySuites - William

2.0 star property
Downtown Pittsburgh
4.0 out of 10, (5)
"The apartment we rented had not been cleaned prior to our arrival. There were dirty linens, dirty handprints on doors and light switches, and when we stripped the bed linens prior to checkout there was a blood stain on the pillow. Yuck!"
United States
Don
$141 nightly
The price is $161
Nov 23 - Nov 24
Total with taxes and fees
CozySuites - William
Apartment | 2 bedrooms
2 Bedroom 2 Bath Downtown Sleeps Six Walkable

2 Bedroom 2 Bath Downtown Sleeps Six Walkable

2.0 star property
Downtown Pittsburgh
10.0 out of 10, Exceptional, (1)
"Basic amenities but excellent customer service. "
United States
Angelika
$112 nightly
The price is $128
Dec 1 - Dec 2
Total with taxes and fees
2 Bedroom 2 Bath Downtown Sleeps Six Walkable
1 bedroom, desk, iron/ironing board, travel crib
*New* Loft 3 min to Local hospitals Sleeps 4

*New* Loft 3 min to Local hospitals Sleeps 4

2.0 star property
Oakland
9.8 out of 10, Exceptional, (14)
"We stayed here for a few days after going to the World Beard and Moustache Championship. It was perfect! We loved this place and the location. The bathroom was great and bidet was a luxury."
United States
Emily M.
$147 nightly
The price is $166
Nov 24 - Nov 25
Total with taxes and fees
*New* Loft 3 min to Local hospitals Sleeps 4
Apartment | Private kitchen | Fridge, microwave, oven, dishwasher
CozySuites at Lawrenceville

CozySuites at Lawrenceville

3.5 star property
Lawrenceville
7.4 out of 10, Good, (3)
"Great hip location walking distance to good food and cute shops. Public bus stop right next to development. Large studio suite decorated hip and modern. Great view of skyline from windows. All dishes and cookware are there if you choose to cook. Neighborhood is really nice and feels safe overall."
United States
Taylor
$181 nightly
The price is $206
Nov 23 - Nov 24
Total with taxes and fees
CozySuites at Lawrenceville
Apartment | 2 bedrooms
6 Beds Downtown Apt Very Quick Walk Everywhere

6 Beds Downtown Apt Very Quick Walk Everywhere

2.0 star property
Downtown Pittsburgh
10.0 out of 10, Exceptional, (2)
"We only stayed for one night went to the Steeler game ! Go Steelers ! Beat the Bengals by the way ! lol the location was great close to stadium. We walked afterwards. There was a couple of good bars in the neighborhood to watch the rest of the games and all it is a perfect spot specially if you're in for a game, I would highly recommend it to any of my friends or family "
United States
John
$149 nightly
The price is $170
Dec 1 - Dec 2
Total with taxes and fees
6 Beds Downtown Apt Very Quick Walk Everywhere
TV
The Light Room

The Light Room

McKeesport
9.6 out of 10, Exceptional, (4)
"The house has a very peaceful atmosphere."
United States
Susan G.
$150 nightly
The price is $170
Nov 27 - Nov 28
Total with taxes and fees
The Light Room
View from property
Not so tiny house with full kitchen & patio swing

Not so tiny house with full kitchen & patio swing

Garfield
9.6 out of 10, Exceptional, (60)
"Really great place for a couple's getaway. "
United States
Zac R.
$170 nightly
The price is $192
Nov 23 - Nov 24
Total with taxes and fees
Not so tiny house with full kitchen & patio swing
Apartment | 1 bedroom
City Views Downtown Apt Walk Everywhere

City Views Downtown Apt Walk Everywhere

2.0 star property
Downtown Pittsburgh
$123 nightly
The price is $140
Nov 23 - Nov 24
Total with taxes and fees
City Views Downtown Apt Walk Everywhere
Front of property
424-Apt. 403

424-Apt. 403

3.5 star property
Oakland
9.6 out of 10, Exceptional, (33)
"The host is wonderful. "
United States
Chaz
$165 nightly
The price is $188
Nov 23 - Nov 24
Total with taxes and fees
424-Apt. 403
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Side Hotel Reviews

Omni William Penn Hotel

Omni William Penn Hotel

10/10 Excellent
"Excellent hotel!"
Alexandru 1-night trip
Posted 15 hours ago
Omni William Penn Hotel

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 $107 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.

Explore a world of travel with Expedia