Search Vacation Homes in South Side

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Compare 446 Vacation Homes in South Side with updated reviews, rates, and availability.

Pittsburgh 2 Bedroom Home on Mt. Washington, Steps away from the Incline

10.0 out of 10, Exceptional, (15)
"As advertised "
The price is ¥20,315
¥48,035 total
includes taxes & fees
Nov 24 - Nov 25
Pittsburgh 2 Bedroom Home on Mt. Washington, Steps away from the Incline

Modern ✌🏾Bedroom House in the ❤️ of Shadyside

9.8 out of 10, Exceptional, (29)
"The property was in a good location, clean and comfortable. The owner was responsive to questions. I woud stay there again. "
Modern ✌🏾Bedroom House in the ❤️ of Shadyside

2 King Beds / Free Parking / Arcade / Patio

10.0 out of 10, Exceptional, (23)
"Nicely decorated place in good neighborhood "
The price is ¥15,323
¥42,502 total
includes taxes & fees
Dec 4 - Dec 5
2 King Beds / Free Parking / Arcade / Patio

Townhouse in Brighton Heights

10.0 out of 10, Exceptional, (18)
"The owner was very responsive and helpful. Place is super clean and roomy. Wish we were here another night!"
The price is ¥18,574
¥33,640 total
includes taxes & fees
Nov 24 - Nov 25
Townhouse in Brighton Heights

Not so tiny house with full kitchen & patio swing

9.6 out of 10, Exceptional, (37)
"Great little place to stay. The ac unit is loud and the front door lacks privacy, but it was a great stay."
The price is ¥15,478
¥29,780 total
includes taxes & fees
Nov 24 - Nov 25
Not so tiny house with full kitchen & patio swing

15 minutes from Downtown, PNC Park, 5 minutes from Monroeville

2.0 out of 10, (5)
"This property looks like a condemned house! Was dirty! No blankets on the beds. Bathroom was unfinished and had no shower curtain. Been trying to get refund from them and getting no responses!! Need to take off Expedia site!! "
The price is ¥18,499
¥26,145 total
includes taxes & fees
Dec 1 - Dec 2
15 minutes from Downtown, PNC Park, 5 minutes from Monroeville

Modern 1BR | FREE Parking | Gym | Skyline Views

9.8 out of 10, Exceptional, (14)
"We loved our stay in Pittsburgh! This condo/ apartment was very nice. The view was spectacular! It had everything we needed. We had plenty of space for my husband and I and we enjoyed the amenities that came with it. We were a walking distance to downtown Pittsburgh and we felt safe and secure. We strongly recommend it!"
Modern 1BR | FREE Parking | Gym | Skyline Views

Downtown Loft | Skyline Views | Free Parking | Gym

10.0 out of 10, Exceptional, (9)
"Perfect location when going to a concert at PPG Paints Arena. Space was exactly as described and communication was excellent with detailed instructions. Will stay here again."
The price is ¥13,930
¥38,695 total
includes taxes & fees
Nov 24 - Nov 25
Downtown Loft | Skyline Views | Free Parking | Gym

Pittsburgh Home Near Frick Park, 7 Mi to Dtwn

9.6 out of 10, Exceptional, (13)
"Cute little neighborhood, easy to walk to local parks & great location for local markets. "
Pittsburgh Home Near Frick Park, 7 Mi to Dtwn

Stay in Style! 4BR Luxury Home w/ Dual Masters, Game Room, Gym & Chef’s Kitchen!

10.0 out of 10, Exceptional, (32)
"We went to Pittsburgh for a Steelers game. The house was located close to the stadium and the airport. The home was immaculate and as described. The kitchen was gorgeous and the hosts were super easy to work with. Would highly recommend. "
The price is ¥28,520
¥82,006 total
includes taxes & fees
Dec 10 - Dec 11
Stay in Style! 4BR Luxury Home w/ Dual Masters, Game Room, Gym & Chef’s Kitchen!

Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.

10.0 out of 10, Exceptional, (11)
"We had a great time and LOVED the house! It was very accommodating, beautiful, relaxing and great for our animals! The owners were very nice and would get back to me asap! We will be staying here again!"
The price is ¥23,062
¥34,017 total
includes taxes & fees
Dec 11 - Dec 12
Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.

Pittsburgh Townhome ~ 5 Miles to Market Square

9.8 out of 10, Exceptional, (27)
"The apartment was as advertised, had everything we needed and a great location. TV operation was a mystery, but that probably had more to do with us than the TV."
Pittsburgh Townhome ~ 5 Miles to Market Square

*8 min WALK Stadium+FREE off-street park+KING BED

10.0 out of 10, Exceptional, (14)
"We recently took a family trip to Pittsburg to watch Clemson play Pittsburgh as we had never been to this area to visit. This place was AWESOME!! It was extremely close to the stadium, convenient to downtown and easy to get to and fro in traffic. From the moment we checked in until we left Caroline was available and willing to help in anyway. She gave great directions and provided all that we needed for a great stay and by far has been the most hospitable host I have ever used on VRBO. I...
The price is ¥22,816
¥50,830 total
includes taxes & fees
Dec 10 - Dec 11
*8 min WALK Stadium+FREE off-street park+KING BED

Stylish Pittsburgh Townhouse w/ City Views!

9.0 out of 10, Wonderful, (11)
"Stayed here with 6 adult family members and a baby over Labor Day weekend. Nice place, lots of room, and an excellent location. Restaurants, breweries, sights, a wedding at the Aviary, we walked pretty much everywhere! The area was quiet and the rooftop lovely. Garage was a definite plus, street parking was pretty easy too. Just be aware that this is not someone’s home, it’s a company rental and is furnished as such, in my opinion. Inexpensive towels, pillows, and other linens. A bare minimum...
Stylish Pittsburgh Townhouse w/ City Views!

Elegant & Cozy Escape - 5Beds/2.5Bath - Sleeps 10

10.0 out of 10, Exceptional, (21)
"Cute, clean place to stay for a larger family. We enjoyed our stay. Loved the private back patio area. We would stay again if in the area! "
Elegant & Cozy Escape - 5Beds/2.5Bath - Sleeps 10

Spacious Loft Downtown | Free Parking | Gym | View

9.8 out of 10, Exceptional, (13)
"Had a wonderful stay in downtown Pittsburgh. The property is in a great location and I love that it was fully stocked. Would stay again."
Spacious Loft Downtown | Free Parking | Gym | View

Beautiful Newly Renovated Home Away from Home

8.6 out of 10, Excellent, (20)
"Great location, clean, beds were comfortable. No issues parking on the street. Only thing I would have liked better is to have the living room furniture be more comfortable. Overall great stay and nice place. Owner was great with communication!"
Beautiful Newly Renovated Home Away from Home

Spaciuos House in Wexford

2.0 star property
10.0 out of 10, Exceptional, (1)
"I needed a place to stay in that area for some events I was attending over the weekend. It was perfect with the only exception being that I wish my family was with me. They would have LOVED all the amenities! "
The price is ¥32,813
¥75,297 total
includes taxes & fees
Nov 30 - Dec 1
Spaciuos House in Wexford

Spacious 3-bedroom house in scenic Mt. Washington near Grandview's city view

2.0 star property
9.0 out of 10, Wonderful, (4)
"The house was very clean, modern, and had lots of amenities (shower products, hairdryer, k-cups, clothes hangers, etc.). There were multiple TV's with many channel options. We walked to Shiloh Street and the incline in less than 10 minutes. I would stay here again. "
Spacious 3-bedroom house in scenic Mt. Washington near Grandview's city view

Stylish 4Bdr Loft Home, North Shore, City Skyline

10.0 out of 10, Exceptional, (22)
"Would definitely stay again. No problems whatsoever Recommend"
The price is ¥27,087
¥75,649 total
includes taxes & fees
Dec 4 - Dec 5
Stylish 4Bdr Loft Home, North Shore, City Skyline
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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Other property types in South Side

Kasa South Side Pittsburgh

4.0 star property
8.6 out of 10, Excellent, (67)
"I love this place! Location of apartment was perfect for me, shops, restaurants, bars within walking distance. Very clean and very comfortable. There’s free parking with a short walk. Easy check in and check out. Highly recommend staying when visiting south Pittsburgh. "
Kasa South Side Pittsburgh

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (20)
"Amazing Place very clean very nice close to everything Host will most definitely will be booking again soon"
The price is ¥6,965
¥37,666 total
includes taxes & fees
Nov 24 - Nov 25
❤️Cozy Townhome on Carey with Private Deck Space ❤️

Breathtaking Spacious PGH Skyline Loft On Carson Street

8.6 out of 10, Excellent, (23)
"This place was perfect for our weekend getaway. Perfect size for a group of guy just there to enjoy the game & even better with a nice rooftop with perfect weather. "
Breathtaking Spacious PGH Skyline Loft On Carson Street
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.