Holiday Homes in South Side

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for South Side holiday homes

Exterior detail

Holiday Home in South Side Flats

Central 5BD Getaway - Spacious Home w/ BBQ
2.0 star property
10.0 out of 10, Exceptional, (10 reviews)
"Great host and property "
United States
Eric G.
Central 5BD Getaway - Spacious Home w/ BBQ
Outdoor dining

Holiday Home in South Side Slopes

City Skyline - Outside decks - Contemporary
10.0 out of 10, Exceptional, (4 reviews)
"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 AU$614
includes taxes & fees
22 Jan - 23 Jan
City Skyline - Outside decks - Contemporary
Property grounds

Holiday Home in South Side Slopes

Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
2.0 star property
The price is AU$464
includes taxes & fees
22 Jan - 23 Jan
Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views
Interior

Holiday Home in South Side Flats

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
2.0 star property
The price is AU$303
includes taxes & fees
22 Jan - 23 Jan
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
Interior

Holiday Home in South Side Flats

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
7.6 out of 10, Good, (9 reviews)
"Home was very comfy children enjoyed there stay I was able to relax and feel comfortable stay I would definitely book again."
United States
bonita f.
The price is AU$358
includes taxes & fees
25 Jan - 26 Jan
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
Interior

Holiday Home in South Side Flats

King Bed - BBQ & Hot Tub - Centrally Located
8.0 out of 10, Very good, (2 reviews)
"It was an excellent stay and a very accurate property description. "
United States
chad s.
The price is AU$567
includes taxes & fees
26 Jan - 27 Jan
King Bed - BBQ & Hot Tub - Centrally Located
Property grounds

Holiday Home in South Side Flats

Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
10.0 out of 10, Exceptional, (20 reviews)
"Fantastic property. Intriguing history. Great location."
United States
Kevin M.
The price is AU$933
includes taxes & fees
24 Jan - 25 Jan
Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces
Terrace/patio

Holiday Home in South Side Slopes

Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!
10.0 out of 10, Exceptional, (16 reviews)
"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 AU$995
includes taxes & fees
22 Jan - 23 Jan
Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!
Outdoor dining

Holiday Home in South Side Flats

Pittsburgh Pennsylvania house
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 AU$411
includes taxes & fees
26 Jan - 27 Jan
Pittsburgh Pennsylvania house
Interior

Holiday Home in Squirrel Hill South

Stylish House near Frick Park
9.8 out of 10, Exceptional, (9 reviews)
"Stayed for the US Open. Check in was easy and property was clean and comfortable. "
United States
Joshua H.
The price is AU$294
includes taxes & fees
26 Jan - 27 Jan
Stylish House near Frick Park
Terrace/patio

Holiday Home in Bloomfield

Fire Pit + Family Friendly + Great Location!
9.8 out of 10, Exceptional, (8 reviews)
"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 AU$385
includes taxes & fees
22 Jan - 23 Jan
Fire Pit + Family Friendly + Great Location!
Smart TV, stereo

Holiday Home in Lawrenceville

★ HostWise Stays ★ Casa Santorini - Aegean Inspired, Instaworthy!
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"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 AU$488
includes taxes & fees
27 Jan - 28 Jan
★ HostWise Stays ★ Casa Santorini - Aegean Inspired, Instaworthy!
TV, table football, books

Holiday Home in North Side

Modern and Spacious House
2.0 star property
9.4 out of 10, Exceptional, (3 reviews)
"Very clean, spacious, and easy parking"
United States
Jessica and Jeff S.
The price is AU$469
includes taxes & fees
26 Jan - 27 Jan
Modern and Spacious House
Property grounds

Holiday Home in Greenfield

Prime 5-Bed: Hot Tub, PITT, CMU, Schenley Park
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Great spot"
United States
Andy R.
Prime 5-Bed: Hot Tub, PITT, CMU, Schenley Park
Fridge, microwave, oven, stovetop

Holiday Home in Brookline

Restful Nest near downtown
9.0 out of 10, Wonderful, (7 reviews)
"Nice quiet neighborhood. Clean and close to places where we wanted to visit. Website and description of amenities need to be updated. There was no hot tub/spa tub, and no washer and dryer. It may have been in the basement, but the door was locked to the lower level. Overall, decent place to stay for the price. "
United States
Peggy A.
The price is AU$449
includes taxes & fees
24 Jan - 25 Jan
Restful Nest near downtown
Interior

Holiday Home in Lawrenceville

★ HostWise Stays ★ 4 Blocks From UPMC Children's
10.0 out of 10, Exceptional, (14 reviews)
"The property was very clean and had all the amenities that made our Pittsburgh visit enjoyable. We enjoyed the location because it was it easy to get where we wanted to go. We would stay here again."
United States
Natalie D.
The price is AU$334
includes taxes & fees
8 Feb - 9 Feb
★ HostWise Stays ★ 4 Blocks From UPMC Children's
Interior

Holiday Home in Monongahela

Charming 4-bedroom family friendly house in Monongahela. Make yourself at home!
10.0 out of 10, Exceptional, (11 reviews)
"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 AU$406
includes taxes & fees
22 Jan - 23 Jan
Charming 4-bedroom family friendly house in Monongahela. Make yourself at home!
Terrace/patio

Holiday Home in Pittsburgh

Modern 3 Bedroom Townhome Close to Downtown
9.6 out of 10, Exceptional, (4 reviews)
"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.
The price is AU$291
includes taxes & fees
26 Jan - 27 Jan
Modern 3 Bedroom Townhome Close to Downtown
Fridge, microwave, oven, stovetop

Holiday Home in Lawrenceville

6min to Pittsburgh Zoo,Pet Friendly,Near Butler St
9.6 out of 10, Exceptional, (20 reviews)
"Very nice."
United States
David D.
The price is AU$836
includes taxes & fees
22 Jan - 23 Jan
6min to Pittsburgh Zoo,Pet Friendly,Near Butler St
Interior

Holiday Home in Lawrenceville

307 37th St · Lawrenceville Row House - Walk to Everything!
9.4 out of 10, Exceptional, (38 reviews)
"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 AU$289
includes taxes & fees
22 Jan - 23 Jan
307 37th St · Lawrenceville Row House - Walk to Everything!
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

DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

10/10 Excellent
"The staff was very friendly and professional. I stayed on the 7th floor, and the room was clean and well maintained. Housekeeping is provided daily, which was a nice touch. The room has a floor to ceiling window where a balcony appears to have once been accessible, though it is no longer in use. There is also a bar and restaurant on the main floor for guests to enjoy. The hotel is only about a 5-minute drive from the city. Overall, it was a good experience."
THADDEUS 7-night trip
Posted 2 days ago
DoubleTree by Hilton Pittsburgh - Green Tree

Find out more about South Side

South Side Holiday Homes information

Number of reviews
153
Accommodation
626 Holiday Homes
Lowest Price
AU$289
Highest Price
AU$995

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