South Side Holiday Rentals

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Our top choices for South Side holiday rentals

1. Spacious 3BR South Side Stay. Near Downtown Pittsburgh

Spacious 3BR South Side Stay. Near Downtown Pittsburgh
South Side Slopes
The price is NZ$497
includes taxes & fees
16 Nov - 17 Nov
Spacious 3BR South Side Stay. Near Downtown Pittsburgh

2. 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.
The price is NZ$342
includes taxes & fees
16 Nov - 17 Nov
2615 Jane Down - Southside

3. The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!

The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!
South Side Flats
7.0 out of 10, Good, (2 reviews)
"It was a nice and beautiful place "
United States
Alyssa B.
The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!

4. 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, (14 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.
The price is NZ$469
includes taxes & fees
17 Nov - 18 Nov
Iron City of South Side Flats Charming 2-bedroom Unit

5. 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.
The price is NZ$482
includes taxes & fees
17 Nov - 18 Nov
Steel City of South Side Flats Charming 2-Bedroom Unit

6. Your Pittsburgh Home Base. 3BR for Families & Groups

Your Pittsburgh Home Base. 3BR for Families & Groups
South Side Slopes
8.0 out of 10, Very good, (1 review)
"Every thing was great"
United States
Taibou C.
The price is NZ$513
includes taxes & fees
16 Nov - 17 Nov
Your Pittsburgh Home Base. 3BR for Families & Groups

7. 3bd 2bath House + Free Parking

3bd 2bath House + 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.
The price is NZ$999
includes taxes & fees
15 Nov - 16 Nov
3bd 2bath House + Free Parking

8. 3-bedroom house in Southside Flats neighborhood of Pittsburgh.

3-bedroom house in Southside Flats neighborhood of Pittsburgh.
South Side Flats
8.0 out of 10, Very good, (3 reviews)
"Place was close to everything ee need the beds and kitchen was clean and the host was very helpful and the check in process was quick and easy"
United States
Alex C.
The price is NZ$430
includes taxes & fees
18 Nov - 19 Nov
3-bedroom house in Southside Flats neighborhood of Pittsburgh.

9. Cozy&Modern 2Bdr Apt PIttsburgh

Cozy&Modern 2Bdr Apt PIttsburgh
South Side Flats
10.0 out of 10, Exceptional, (20 reviews)
"Great location, very clean, and exactly as described. We had a wonderful stay and would definitely stay here again! "
United States
Abby S.
The price is NZ$263
includes taxes & fees
15 Nov - 16 Nov
Cozy&Modern 2Bdr Apt PIttsburgh

10. 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.
The price is NZ$458
includes taxes & fees
16 Nov - 17 Nov
Pittsburgh Pennsylvania house

11. Sleeps 10 · Walk to Carson St · BBQ & Fire Pit

Sleeps 10 · Walk to Carson St · BBQ & Fire Pit
South Side Flats
The price is NZ$677
includes taxes & fees
15 Nov - 16 Nov
Sleeps 10 · Walk to Carson St · BBQ & Fire Pit

12. Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge
Allentown
9.8 out of 10, Exceptional, (6 reviews)
"Very nice place perfect for my needs."
United States
John
The price is NZ$551
includes taxes & fees
15 Nov - 16 Nov
Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

13. Pittsburgh South Side, 6BR Group Stay, 3 Baths, Sleeps 18

Pittsburgh South Side, 6BR Group Stay, 3 Baths, Sleeps 18
South Side Slopes
The price is NZ$1,010
includes taxes & fees
15 Nov - 16 Nov
Pittsburgh South Side, 6BR Group Stay, 3 Baths, Sleeps 18

14. Cozy Loft Studio in a Triplex, near SouthSideWorks

Cozy Loft Studio in a Triplex, near SouthSideWorks
South Side Flats
8.0 out of 10, Very good, (2 reviews)
"Great communication"
United States
Clay B.
The price is NZ$276
includes taxes & fees
16 Nov - 17 Nov
Cozy Loft Studio in a Triplex, near SouthSideWorks

15. City Skyline - Outside decks - Contemporary

City Skyline - Outside decks - Contemporary
South Side Slopes
10.0 out of 10, Exceptional, (12 reviews)
"We had a great stay in this beautiful home! The host was super responsive and helpful. The home is spacious and well kept with amazing views of the city. The cherry on top was the driveway/parking area that accommodated our five vehicles. Great choice for our family get together!"
United States
Mary H.
The price is NZ$834
includes taxes & fees
16 Nov - 17 Nov
City Skyline - Outside decks - Contemporary

16. King Bed | Garage Door Patio | Free Parking

King Bed | Garage Door Patio | Free Parking
South Side Flats
9.6 out of 10, Exceptional, (33 reviews)
"Great stay ! "
United States
Vidal R.
The price is NZ$825
includes taxes & fees
2 Dec - 3 Dec
King Bed | Garage Door Patio | Free Parking

17. 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, (7 reviews)
"Great stay! Rooms were comfortable and very clean. "
United States
Anonymous traveller
The price is NZ$637
includes taxes & fees
16 Nov - 17 Nov
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views

18. *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.
The price is NZ$561
includes taxes & fees
16 Nov - 17 Nov
*Historic Gem* Heart of Southside-Sleeps 10

19. 4 Bedroom Beauty Spacious Home in Southside

4 Bedroom Beauty Spacious Home in Southside
South Side Flats
9.0 out of 10, Wonderful, (2 reviews)
"Very convenient location. "
United States
Rachel S.
The price is NZ$765
includes taxes & fees
28 Nov - 29 Nov
4 Bedroom Beauty Spacious Home in Southside

20. 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)
"Great host and property "
United States
Eric G.
The price is NZ$1,068
includes taxes & fees
15 Nov - 16 Nov
Central 5BD Getaway - Spacious Home w/ BBQ
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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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, 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 NZ$261 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.

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