Search Vacation Homes in South Side

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Our top choices for South Side holiday homes

Holiday Home in South Side Slopes

City Skyline - Outside decks - Contemporary
10.0 out of 10, Exceptional, (4)
"We appreciated the way most everything was as shown in photos and loved the 4 furnished decks. The owner quickly responded to our needs and questions. Nice to have parking not on street."
United States
Deborah C.
The price is HK$999
HK$3,220 total
includes taxes & fees
8 Jan - 9 Jan
City Skyline - Outside decks - Contemporary

Holiday Home in South Side Flats

Central 5BD Getaway - Spacious Home w/ BBQ
2.0 star property
10.0 out of 10, Exceptional, (10)
"Great host and property "
United States
Eric G.
The price is HK$1,177
HK$3,423 total
includes taxes & fees
8 Jan - 9 Jan
Central 5BD Getaway - Spacious Home w/ BBQ
2.0 star property
The price is HK$637
HK$1,558 total
includes taxes & fees
8 Jan - 9 Jan
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
8.4 out of 10, Very good, (33)
"This house worked excellent for our family to stay for the weekend for college graduation. Perfect location to get around and see South Side."
United States
Michael P.
❤️Cozy Townhome on Carey with Private Deck Space ❤️
2.0 star property
The price is HK$884
HK$2,492 total
includes taxes & fees
8 Jan - 9 Jan
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
10.0 out of 10, Exceptional, (16)
"Great stay! Very good location to get to the city and great restaurants. Amazing view! The host was very nice and great to work with. "
United States
Eric A.
The price is HK$2,492
HK$5,233 total
includes taxes & fees
8 Jan - 9 Jan
Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!
10.0 out of 10, Exceptional, (20)
"Fantastic property. Intriguing history. Great location."
United States
Kevin M.
The price is HK$2,617
HK$4,831 total
includes taxes & fees
13 Jan - 14 Jan
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

Holiday Home in South Side Flats

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. "
United States
chad s.
The price is HK$1,025
HK$3,019 total
includes taxes & fees
14 Jan - 15 Jan
King Bed - BBQ & Hot Tub - Centrally Located

Holiday Home in South Side Flats

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."
United States
Adrian C.
The price is HK$1,148
HK$2,405 total
includes taxes & fees
8 Jan - 9 Jan
Pittsburgh Pennsylvania house
10.0 out of 10, Exceptional, (14)
"Great location and communication from host! The home was clean, comfortable, and exactly as described. We loved and appreciated the kitchen amenities! We very much enjoyed our stay. We would absolutely stay here again and highly recommend this rental. "
United States
Heather S.
The price is HK$515
HK$1,455 total
includes taxes & fees
13 Jan - 14 Jan
★ HostWise Stays ★ 4 Blocks From UPMC Children's
9.8 out of 10, Exceptional, (7)
"The house was very comfortable for our family. Great location in walking distance to eateries, breweries, coffee shops, grocery and drug stores. Easy access to downtown. We would stay there again on our next visit. "
United States
shely c.
The price is HK$657
HK$2,022 total
includes taxes & fees
8 Jan - 9 Jan
Fire Pit + Family Friendly + Great Location!
2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay during our visit to Pittsburgh. Our host Chad was very helpful and responsive when we had questions. It was our first time in Lawrenceville and it exceeded our expectations! Love the neighborhood and its vibe! Looking forward to our next trip! "
United States
Terri W.
The price is HK$790
HK$2,612 total
includes taxes & fees
14 Jan - 15 Jan
★ HostWise Stays ★ Casa Santorini - Aegean Inspired, Instaworthy!

Holiday Home in North Side

Modern and Spacious House
2.0 star property
9.4 out of 10, Exceptional, (3)
"Very clean, spacious, and easy parking"
United States
Jessica and Jeff S.
The price is HK$911
HK$2,654 total
includes taxes & fees
8 Jan - 9 Jan
Modern and Spacious House

Holiday Home in Squirrel Hill South

Stylish House near Frick Park
9.8 out of 10, Exceptional, (9)
"Stayed for the US Open. Check in was easy and property was clean and comfortable. "
United States
Joshua H.
The price is HK$654
HK$1,540 total
includes taxes & fees
8 Jan - 9 Jan
Stylish House near Frick Park
10.0 out of 10, Exceptional, (11)
"Great girls trip at the Blue Peacock. House has plenty of room and is cozy. Location is good too.Andres answered all our questions promptly.Would recommend & stay again!"
United States
Stephanie M.
The price is HK$881
HK$2,022 total
includes taxes & fees
13 Jan - 14 Jan
Charming 4-bedroom family friendly house in Monongahela. Make yourself at home!
10.0 out of 10, Exceptional, (4)
"Great stay Chad was awesome loved the place close to what I was doing in proximity "
United States
Robert M.
The price is HK$772
HK$2,073 total
includes taxes & fees
13 Jan - 14 Jan
**HostWise Stays** - Pet Friendly, Patio, Great for Long Stays!
10.0 out of 10, Exceptional, (4)
"Great location! Very clean, street is super quiet"
United States
Daryll J.
The price is HK$523
HK$1,340 total
includes taxes & fees
4 Feb - 5 Feb
★ HostWise Stays ★ Le Petit Riad: A Moroccan Oasis Tiny Home
9.6 out of 10, Exceptional, (4)
"This was a very tidy, updated duplex. Clean, everything you could want or need in the kitchen. The deck was really nice with lots of space to visit and we had great weather to enjoy it. We had a group of 5 adults and the space worked great but you must go upstairs for bedrooms and bath so keep that in mind."
United States
Kerri D.
Modern 3 Bedroom Townhome Close to Downtown
9.4 out of 10, Exceptional, (38)
"We loved staying here! The unit was in a quiet and safe location, it was clean and spacious, and had everything we needed. I would highly recommend it. "
United States
Melissa S.
The price is HK$642
HK$1,471 total
includes taxes & fees
13 Jan - 14 Jan
307 37th St · Lawrenceville Row House - Walk to Everything!

Holiday Home in Brookline

Restful Nest near downtown
9.0 out of 10, Wonderful, (7)
"This house was perfect for our weekend stay for the Steelers game. It is just a few miles drive to the stadium. There is a large variety of restaurants close by. The house was clean and comfortable and well stocked with whatever you may need for your stay."
United States
Mark D.
The price is HK$876
HK$2,314 total
includes taxes & fees
13 Jan - 14 Jan
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

Find out more about South Side

South Side Vacation Homes information

Number of reviews
179
Accommodation
626 Vacation Homes
Lowest Price
HK$1,340
Highest Price
HK$5,233

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