South Side Vacation Rentals

    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

Vacation Rentals in South Side

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

❤️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 CA $76
CA $355 total
includes taxes & fees
Aug 20 - Aug 21
❤️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 CA $165
CA $455 total
includes taxes & fees
Aug 26 - Aug 27
Charming 2-bedroom apartment In Pittsburgh, Southside!

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! "
The price is CA $62
CA $334 total
includes taxes & fees
Aug 20 - Aug 21
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

*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 CA $200
CA $391 total
includes taxes & fees
Aug 26 - Aug 27
*Historic Gem* Heart of Southside-Sleeps 10

Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside

6.0 out of 10, (3)
"Excellent communication with owner. Fast, friendly and courteous. Located about 450 meter walk up a large hill from Penn Avenue (bus 88) which is about 35 minutes to downtown. Apartment showing its age but fair value for cost. "
The price is CA $165
CA $455 total
includes taxes & fees
Aug 19 - Aug 20
Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside

Cozy&Modern 2Bdr Apt PIttsburgh

2.0 star property
10.0 out of 10, Exceptional, (4)
"Good location right of East Carson. Enjoyed our stay."
The price is CA $149
CA $199 total
includes taxes & fees
Aug 14 - Aug 15
Cozy&Modern 2Bdr Apt PIttsburgh

Stay Pittsburgh

2.0 star property
7.8 out of 10, Good, (168)
"Clean and good location "
The price is CA $79
CA $161 total
includes taxes & fees
Sep 1 - Sep 2
Stay Pittsburgh

Placemakr Downtown Pittsburgh at The Pennsylvanian

4.0 star property
8.0 out of 10, Very good, (14)
"The unit we stayed in was impeccable. Very beautifully decorated and comfy and homelike. Would definitely stay there again. "
The price is CA $143
CA $163 total
includes taxes & fees
Aug 24 - Aug 25
Placemakr Downtown Pittsburgh at The Pennsylvanian

Abode Pittsburgh - Downtown Convention Center

3.5 star property
7.6 out of 10, Good, (82)
"Location nice"
The price is CA $91
CA $259 total
includes taxes & fees
Aug 25 - Aug 26
Abode Pittsburgh - Downtown Convention Center

Stylish & Central 3BD Home Pittsburgh/North Side

10.0 out of 10, Exceptional, (9)
"Super clean and comfortable. Centrally located. Great for family. Everyone enjoyed their stay."
The price is CA $121
CA $171 total
includes taxes & fees
Aug 14 - Aug 15
Stylish & Central 3BD Home Pittsburgh/North Side

Melwood Suites Unit 107 Studio

2.0 star property
9.6 out of 10, Exceptional, (29)
"We loved how modern and quiet the place was."
The price is CA $176
CA $201 total
includes taxes & fees
Aug 26 - Aug 27
Melwood Suites Unit 107 Studio

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

2.0 star property
9.8 out of 10, Exceptional, (17)
"Great house and great location. Walking distance to several bars, restaurants and the incline. Great views. "
Spacious 3-bedroom house in scenic Mt. Washington near Grandview's city view

Melwood Suites Unit 106 Studio

2.0 star property
9.4 out of 10, Exceptional, (3)
"Best stay ever! And I’ve been many places. "
The price is CA $149
CA $273 total
includes taxes & fees
Aug 19 - Aug 20
Melwood Suites Unit 106 Studio

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 CA $94
CA $248 total
includes taxes & fees
Aug 19 - Aug 20
CozySuites - Press House

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!

Stylish 4Bdr Loft Home, North Shore, City Skyline

10.0 out of 10, Exceptional, (28)
"Would definitely stay again. No problems whatsoever Recommend"
The price is CA $161
CA $218 total
includes taxes & fees
Aug 17 - Aug 18
Stylish 4Bdr Loft Home, North Shore, City Skyline

424-Apt. 403

3.5 star property
9.8 out of 10, Exceptional, (30)
"It was a beautiful place. We really enjoyed our stay. "
The price is CA $184
CA $297 total
includes taxes & fees
Aug 26 - Aug 27
424-Apt. 403

6 Beds Downtown Apt Very Quick Walk Everywhere

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is CA $193
CA $296 total
includes taxes & fees
Sep 1 - Sep 2
6 Beds Downtown Apt Very Quick Walk Everywhere

Cozy City Views Apartment downtown perfect location with rooftop and gym

10.0 out of 10, Exceptional, (5)
The price is CA $136
CA $278 total
includes taxes & fees
Aug 28 - Aug 29
Cozy City Views Apartment downtown perfect location with rooftop and gym
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

Frequently asked questions

Are there vacation rentals in South Side?

Yes, you can find vacation rentals close to top attractions in South Side, or you can go with a more remote option if you'd like a relaxing place to stay. Our travelers say South Side has a good selection of lively bars and top-notch restaurants. The theater scene and live music are some other things you might like to check out during your trip.

What are some of the best vacation rentals that South Side has to offer?

Convenient Getaway : This South Side vacation home rental is equipped with a patio, laundry facilities, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave, and a coffee maker. Other favorite homes for rent in South Side are Charming 2BD/3BM home w/fireplace/hut tub/private patio and Gorgeous Southside Slopes home with outdoor hot tub and city view!.

How many vacation rentals will I find in South Side?

Choose from 59 Expedia vacation rentals in South Side for a memorable vacation.

What can I see and do in South Side?

Explore the area and family-friendly sights such as Senator John Heinz Regional History Centre, or get out into nature at a spot like PNC Park. While in the area, you can also visit popular places like PPG Paints Arena and Acrisure Stadium.

What are vacation rentals like in South Side?

Vacation rentals are privately owned properties you can stay in for a couple days or more in South Side. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips.