Holiday Rentals in South Side

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in South Side

Our top choices for South Side holiday rentals

Kasa South Side Pittsburgh

4.0 star property
8.2 out of 10, Very good, (89)
"Surprised at the room cleanliness. This is our 4th time staying at this property. And the no parking was a little disappointing."
Kasa South Side Pittsburgh

Walkable Studio in the Heart of Pittsburgh!

3.0 star property
Walkable Studio in the Heart of Pittsburgh!

Cozy&Modern 2Bdr Apt PIttsburgh

2.0 star property
10.0 out of 10, Exceptional, (5)
"Good location right of East Carson. Enjoyed our stay."
Cozy&Modern 2Bdr Apt PIttsburgh

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (26)
"got a lil warm in the house the first night but over all a great place"
The price is €213
includes taxes & fees
1 Sept - 2 Sept
❤️Cozy Townhome on Carey with Private Deck Space ❤️

Charming 2-bedroom apartment In Pittsburgh, Southside!

4.0 out of 10, (3)
"The apartment itself is lovely. There is one reason I would not stay here is there is a horrible gut wrenching smell in hallway and the entire apartment. At first we thought someone was cooking with very intense spices until we got inside apartment and it smelled the same with same intensity. This smell did not go away for the two days we were there. Only relief we got was when opening windows. Luckily had air freshener in the car. There were plug-ins but only one had deodorizer in it. The host...
The price is €289
includes taxes & fees
26 Aug - 27 Aug
Charming 2-bedroom apartment In Pittsburgh, Southside!

King Bed | Free Parking | Arcade | Fire Pit

10.0 out of 10, Exceptional, (17)
"Very easy to use and so many great amenities!"
The price is €291
includes taxes & fees
24 Sept - 25 Sept
King Bed | Free Parking | Arcade | Fire Pit

*Historic Gem* Heart of Southside-Sleeps 10

9.6 out of 10, Exceptional, (18)
"Property was perfect for a quick weekend visit to attend a concert at PPG arena. "
The price is €250
includes taxes & fees
26 Aug - 27 Aug
*Historic Gem* Heart of Southside-Sleeps 10

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

9.4 out of 10, Exceptional, (3)
"Tom was very communicative during the whole stay and had great recommendations! We loved the place, well situated on the South side for easy walking along Carson. Wonderful time in Pittsburgh! "
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

Stay Pittsburgh

2.0 star property
7.8 out of 10, Good, (169)
"Clean and good location "
The price is €105
includes taxes & fees
26 Aug - 27 Aug
Stay Pittsburgh

Placemakr Downtown Pittsburgh at The Pennsylvanian

4.0 star property
7.6 out of 10, Good, (19)
"The unit we stayed in was impeccable. Very beautifully decorated and comfy and homelike. Would definitely stay there again. "
The price is €155
includes taxes & fees
31 Aug - 1 Sept
Placemakr Downtown Pittsburgh at The Pennsylvanian

Melwood Suites Unit 107 Studio

2.0 star property
9.6 out of 10, Exceptional, (30)
"We loved how modern and quiet the place was."
The price is €112
includes taxes & fees
26 Aug - 27 Aug
Melwood Suites Unit 107 Studio

Abode Pittsburgh - Downtown Convention Center

3.5 star property
7.6 out of 10, Good, (82)
"Location nice"
The price is €144
includes taxes & fees
1 Sept - 2 Sept
Abode Pittsburgh - Downtown Convention Center

Stylish & Central 3BD Home Pittsburgh/North Side

10.0 out of 10, Exceptional, (11)
"Super clean and comfortable. Centrally located. Great for family. Everyone enjoyed their stay."
The price is €110
includes taxes & fees
26 Aug - 27 Aug
Stylish & Central 3BD Home Pittsburgh/North Side

*New* Loft 3 min to Local hospitals Sleeps 4

2.0 star property
10.0 out of 10, Exceptional, (8)
"Very cool space. Immediate area is sparse. But a quick walk or drive and tons to see and do. "
The price is €137
includes taxes & fees
26 Aug - 27 Aug
*New* Loft 3 min to Local hospitals Sleeps 4

Downtown Estate! Can sleep up to 24!

10.0 out of 10, Exceptional, (1)
"Was in town for an unfortunate situation due to a family member needing an emergency surgery and was a little worried about booking a property with no reviews, but after speaking with the owner, I was put at ease and let me tell you this property is not only in a great location, but also such a beautiful property and the house even provided breakfast, pastries, and snacks as well as drinks so definitely already looking into booking another trip out to Pittsburgh just to stay here! "
Downtown Estate! Can sleep up to 24!

Spacious 6-bedroom house in mt washington with pokerroom

The price is €623
includes taxes & fees
26 Aug - 27 Aug
Spacious 6-bedroom house in mt washington with pokerroom

Spacious 3-bedroom house in scenic Mt. Washington near Grandview's city view

2.0 star property
9.8 out of 10, Exceptional, (18)
"House was clean and exactly as described in the listing, had a wonderful time in Mt Washington!"
Spacious 3-bedroom house in scenic Mt. Washington near Grandview's city view

CozySuites - William

2.0 star property
3.0 out of 10, (4)
"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!"
The price is €144
includes taxes & fees
26 Aug - 27 Aug
CozySuites - William

Stylish 4Bdr Loft Home, North Shore, City Skyline

9.6 out of 10, Exceptional, (31)
"Would definitely stay again. No problems whatsoever Recommend"
The price is €138
includes taxes & fees
26 Aug - 27 Aug
Stylish 4Bdr Loft Home, North Shore, City Skyline

CozySuites - Press House

2.0 star property
4.0 out of 10, (2)
"Nice area in downtown Pittsburg PA. It was roomy. Furniture was cheap but we understand why. "
The price is €154
includes taxes & fees
26 Aug - 27 Aug
CozySuites - Press House
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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Side Hotel Reviews

Find out more about South Side

Find out more about South Side

Everything you need to know about South Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Side holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Side holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Side holiday rentals we have selected for you start as low as €105 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Side rentals

At Expedia, we put the best South Side holiday 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 holiday.

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.