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Vacation Homes in South Side

Our top choices for South Side vacation homes

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 ¥13,970
¥46,618 total
includes taxes & fees
Sep 30 - Oct 1
King Bed | Free Parking | Arcade | Fire Pit

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 ¥5,881
¥33,108 total
includes taxes & fees
Sep 15 - Sep 16
Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside

Charming and luxurious 2-bed house in Pittsburgh with AC

The price is ¥15,482
¥35,306 total
includes taxes & fees
Sep 3 - Sep 4
Charming and luxurious 2-bed house in Pittsburgh with AC

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

8.0 out of 10, Very Good, (5)
"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 ¥7,352
¥36,776 total
includes taxes & fees
Sep 3 - Sep 4
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

❤️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 ¥6,616
¥36,094 total
includes taxes & fees
Aug 31 - Sep 1
❤️Cozy Townhome on Carey with Private Deck Space ❤️

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

The price is ¥25,730
¥76,013 total
includes taxes & fees
Sep 3 - Sep 4
King Bed • Garage • Rooftop Views • Sleeps 14 • Game room • walk to Carson St

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

The price is ¥19,996
¥68,689 total
includes taxes & fees
Aug 31 - Sep 1
King bed I 1 block to Carson l Game Room l Fire Pit l BBQ l Sleeps 10 l AC l

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 ¥21,305
¥64,680 total
includes taxes & fees
Sep 3 - Sep 4
City Skyline - Outside decks - Contemporary

Hot Tub | Arcade | King Bed | Free Parking

10.0 out of 10, Exceptional, (1)
The price is ¥21,025
¥55,321 total
includes taxes & fees
Sep 23 - Sep 24
Hot Tub | Arcade | King Bed | Free Parking

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 ¥18,820
¥55,367 total
includes taxes & fees
Sep 9 - Sep 10
King Bed | Free Parking | BBQ | Fire pit | Arcade

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 ¥7,352
¥35,100 total
includes taxes & fees
Sep 8 - Sep 9
Charming 2-bedroom apartment In Pittsburgh, Southside!

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

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."
The price is ¥17,952
¥42,729 total
includes taxes & fees
Aug 31 - Sep 1
Pittsburgh Pennsylvania house

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."
The price is ¥49,402
¥92,001 total
includes taxes & fees
Sep 9 - Sep 10
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

Iconic 3BD Entire House in The Heart Of Pittsburg

2.0 star property
The price is ¥27,008
¥57,762 total
includes taxes & fees
Sep 3 - Sep 4
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!"
The price is ¥17,497
¥54,804 total
includes taxes & fees
Sep 2 - Sep 3
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 ¥32,200
¥58,976 total
includes taxes & fees
Sep 24 - Sep 25
Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions

Spacious & Elegant • Mins to Hospital

2.0 star property
10.0 out of 10, Exceptional, (4)
"The place was amazing! Very clean and accomadating. I would choose this over any hotel. The only thing to note are that the beds were very firm. "
The price is ¥18,673
¥53,782 total
includes taxes & fees
Sep 3 - Sep 4
Spacious & Elegant • Mins to Hospital

Yinz Retreat, Above the City Home

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place to stay at, loved the ambiance, the view of the city was amazing. It is spacious, and the top floor is great for adults and kids to just hang out in. Would definitely book again when we come back out here. "
The price is ¥27,571
¥77,380 total
includes taxes & fees
Sep 1 - Sep 2
Yinz Retreat, Above the City Home

Modern Family Friendly Home - 3 Bed Great Location

2.0 star property
10.0 out of 10, Exceptional, (3)
"Very much enjoyed our stay. Great communication from the property management "
Modern Family Friendly Home - 3 Bed Great Location
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

Find out more about South Side

Find out more about South Side

South Side Vacation Homes information

Number of reviews
85
Accommodation
690 Vacation Homes
Lowest Price
¥6,616
Highest Price
¥58,812

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