Holiday Homes in South Side

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Featured Holiday Homes in South Side and around

Our top choices for South Side holiday homes

Charming and luxurious 2-bed house in Pittsburgh with AC

The price is €202
includes taxes & fees
1 Sept - 2 Sept
Charming and luxurious 2-bed house in Pittsburgh with AC

Central 5BD Getaway - Spacious Home w/ BBQ

2.0 star property
10.0 out of 10, Exceptional, (8)
"House was absolutely perfect for our big family trip to Pittsburgh! House was very clean, beds were comfortable and the outside was amazing! We all would recommend and absolutely would stay again!"
Central 5BD Getaway - Spacious Home w/ BBQ

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 €292
includes taxes & fees
24 Sept - 25 Sept
King Bed | Free Parking | Arcade | Fire Pit

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!

King bed I 1 block to Carson l Game Room l Fire Pit l BBQ l Sleeps 10 l AC l

The price is €409
includes taxes & fees
25 Aug - 26 Aug
King bed I 1 block to Carson l Game Room l Fire Pit l BBQ l Sleeps 10 l AC l

❤️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 €225
includes taxes & fees
31 Aug - 1 Sept
❤️Cozy Townhome on Carey with Private Deck Space ❤️

King Bed • Garage • Rooftop Views • Sleeps 14 • Game room • walk to Carson St

The price is €452
includes taxes & fees
25 Aug - 26 Aug
King Bed • Garage • Rooftop Views • Sleeps 14 • Game room • walk to Carson St

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

City Skyline - Outside decks - Contemporary

10.0 out of 10, Exceptional, (3)
"House was perfect for our small gathering of family and friends. We lived out on the decks where the view is spectacular. Host could not have been better. Thanks for a perfect stay!"
The price is €366
includes taxes & fees
25 Aug - 26 Aug
City Skyline - Outside decks - Contemporary

King Bed - BBQ & Hot Tub - Centrally Located

8.0 out of 10, Very good, (2)
"It was an excellent stay and a very accurate property description. "
The price is €339
includes taxes & fees
25 Aug - 26 Aug
King Bed - BBQ & Hot Tub - Centrally Located

King Bed | Free Parking | BBQ | Fire pit | Arcade

9.6 out of 10, Exceptional, (59)
"We stayed over the Christmas holiday and really enjoyed the townhouse - lots of privacy and room for the whole family. Also loved the convenient location. "
The price is €342
includes taxes & fees
1 Sept - 2 Sept
King Bed | Free Parking | BBQ | Fire pit | Arcade

Hot Tub | Arcade | King Bed | Free Parking

10.0 out of 10, Exceptional, (1)
Hot Tub | Arcade | King Bed | Free Parking

Pittsburgh Gem - 5BR - Downtown Deck View

10.0 out of 10, Exceptional, (4)
"The place was as advertised. Plenty of space for 6 of us. Would reserve again."
Pittsburgh Gem - 5BR - Downtown Deck View

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
25 Aug - 26 Aug
Charming 2-bedroom apartment In Pittsburgh, Southside!

Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

10.0 out of 10, Exceptional, (15)
"House was fabulous, decorated beautifully, and host added all the warm-welcoming touches from beautiful flowers to home-made treats."
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

Pittsburgh Pennsylvania house

6.0 out of 10, (2)
"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."
Pittsburgh Pennsylvania house

Iconic 3BD Entire House in The Heart Of Pittsburg

2.0 star property
The price is €335
includes taxes & fees
8 Sept - 9 Sept
Iconic 3BD Entire House in The Heart Of Pittsburg

Accessible • Family Friendly • Safe Locale

9.8 out of 10, Exceptional, (18)
"Super cute house, lots of street parking, pet friendly. Host was very nice and responsive. Great place to stay!"
Accessible • Family Friendly • Safe Locale

Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions

2.0 star property
8.4 out of 10, Very good, (7)
"This is one of my favorite locations I’ve stayed at. The house is lovely, clean, comfortable, quiet, has everything you need, the pool and hot tub are fantastic, and it’s close to anywhere you want to go while feeling like a hideaway retreat. I’m already looking forward to coming back! "
The price is €349
includes taxes & fees
24 Sept - 25 Sept
Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions

Restful Nest near downtown

9.0 out of 10, Wonderful, (6)
"Stayed over after concert and avoided all the traffic. Convenient to Station Square parking and Gateway Clipper. Owner very responsive to messages and questions. Comfortable beds, clean and updated."
Restful Nest near downtown
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