Holiday Homes in South Side

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Featured Holiday Homes in South Side

307 37th St · Lawrenceville Row House - Walk to Everything!
TV

307 37th St · Lawrenceville Row House - Walk to Everything!

9.4 out of 10, Exceptional, (22)
"Overall my family and I were comfortable in this home. Check-in and out were smooth, and we thought the amenities provided were good. We only stayed for one night, so I could not really request anything in the moment. Some of the bedding was not that clean and smelled like body odor. The shower ran out of water after 2 pretty quick showers -- I think a heads-up from the owners would have helped. I told this feedback to the owners and they were very nice about it. Hopefully future stays with...
The price is AU$280
includes taxes & fees
13 Jan - 14 Jan 2025
307 37th St · Lawrenceville Row House - Walk to Everything!
Luxurious 4BR Urban Oasis Sleeps 12 Pets OK Private Backyard & 2 Car Garage
Fridge, microwave, oven, stovetop

Luxurious 4BR Urban Oasis Sleeps 12 Pets OK Private Backyard & 2 Car Garage

9.8 out of 10, Exceptional, (41)
"Great place to stay if going into the city for dinner and the theater. Location was convenient and the property was clean and very roomy for 3 couples."
The price is AU$665
includes taxes & fees
14 Jan - 15 Jan 2025
Luxurious 4BR Urban Oasis Sleeps 12 Pets OK Private Backyard & 2 Car Garage
Cozy Pittsburgh Home with King Beds - short drive to all
Dining

Cozy Pittsburgh Home with King Beds - short drive to all

9.4 out of 10, Exceptional, (19)
"This was in a convenient location for our trip, beds were great. Would definitely stay again if in the area."
Cozy Pittsburgh Home with King Beds - short drive to all
Home away from home!!!
Living area

Home away from home!!!

8.2 out of 10, Very good, (20)
"Overall well. I wish the unit was a little cleaner. The property is beautiful so a little more TLC would have been good. The downstairs area needed cleaned. The bathroom floor wasn’t clean. The toilet wasn’t clean but I cleaned everything to my liking upon checking in and it made our stay better. We felt safe and enjoyed to fireplace lights."
The price is AU$1,028
includes taxes & fees
1 Jan - 2 Jan 2025
Home away from home!!!
Modern 1BR | FREE Parking | Gym | Skyline Views
Fridge, microwave, oven, stovetop

Modern 1BR | FREE Parking | Gym | Skyline Views

9.8 out of 10, Exceptional, (16)
"The location is phenomenal for events at PPG Arena - in fact, I don't think it can get any better. The apartment is clean, quiet, and well maintained. Getting in and out is super easy. The lobby staff is friendly and helpful and there's a Starbucks attached to the lobby - which was an added bonus. I forgot a few minor things (shampoo,etc.) and host had that readily available in the unit. The bed is unacceptable. It's out of place in such a nice apartment, especially for the cost. It...
Modern 1BR | FREE Parking | Gym | Skyline Views
Downtown Loft | Skyline Views | Free Parking | Gym
TV, offices

Downtown Loft | Skyline Views | Free Parking | Gym

10.0 out of 10, Exceptional, (12)
"The condo is amazing. It has everything you could possibly need or want for an enjoyable stay in Pittsburgh. The location is ideal for whatever it is you plan to do while you are in town. The host is very responsive, courteous and professional. We will definitely stay here again on our next trip to Pittsburgh."
The price is AU$402
includes taxes & fees
29 Dec - 30 Dec
Downtown Loft | Skyline Views | Free Parking | Gym
Elegant & Cozy Escape - 5Beds/2.5Bath - Sleeps 10
Fridge, microwave, oven, stovetop

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
Downtown Escape: 3Br - Game/Movie Room - Foosball
Fridge, microwave, oven, stovetop

Downtown Escape: 3Br - Game/Movie Room - Foosball

9.2 out of 10, Wonderful, (5)
"Perfect spot in the heart of the city! Great style and comfort. Gracious host! "
Downtown Escape: 3Br - Game/Movie Room - Foosball
Spacious Pitt Loft | Walkable | Gym |Free Parking
Interior

Spacious Pitt Loft | Walkable | Gym |Free Parking

9.2 out of 10, Wonderful, (7)
"We really enjoyed staying at this property. The condo itself is very nice/clean and we felt extra safe with the security in the lobby. The parking is an extra bonus. We walked everywhere, including to Acrisure Stadium! Highly recommend staying here."
The price is AU$419
includes taxes & fees
29 Dec - 30 Dec
Spacious Pitt Loft | Walkable | Gym |Free Parking
Beautiful Newly Renovated Home Away from Home
Fridge, microwave, oven, stovetop

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
Spacious Downtown Loft | Free Parking | Gym
Interior

Spacious Downtown Loft | Free Parking | Gym

9.6 out of 10, Exceptional, (22)
"."
The price is AU$402
includes taxes & fees
13 Jan - 14 Jan 2025
Spacious Downtown Loft | Free Parking | Gym
❤️Cozy Townhome on Carey with Private Deck Space ❤️
Exterior

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (22)
"Property was as advertised. Clean, Great location. Had the kitchen items we needed. Plenty of room for all. Worked well for 4 of us. Beds could have been a little more comfortable on the main level. Upper level beds comfortable. Lots of stairs. But most South side flat properties will have lots of stairs. Location made up for all of that and we were satisfied. The host communicated perfectly, timely and met our needs.Clean property. Definitely worth what we paid for it. Mike"
The price is AU$407
includes taxes & fees
1 Jan - 2 Jan 2025
❤️Cozy Townhome on Carey with Private Deck Space ❤️
Urban Retreat with Garage on Mt Washington
Property grounds

Urban Retreat with Garage on Mt Washington

9.8 out of 10, Exceptional, (37)
"This house was very clean and comfortable. It was also well equipped for cooking. The streets surrounding it are very narrow, which is common in that area but if you have a choice, I would take the smaller car. With that being said, we did just fine with my full size tri k. "
The price is AU$319
includes taxes & fees
13 Jan - 14 Jan 2025
Urban Retreat with Garage on Mt Washington
Cozy escape close to downtown, stadiums & parks
Smart TV, DVD player, books, video library

Cozy escape close to downtown, stadiums & parks

10.0 out of 10, Exceptional, (34)
"I've been to Pittsburgh twice before this trip, but never spending much time inside the city itself. Having a spot that was clean, easy to access and cozy to come back to in between running around downtown and a wedding was perfect! Pearl was honestly the highlight of the stay- I dont think I've ever met.a sweeter cat. The property owner was so quick to reply with any questions I had, but honestly it was a hands-off stay, because they made it so easy from the start. Thanks for adding to a...
The price is AU$275
includes taxes & fees
14 Jan - 15 Jan 2025
Cozy escape close to downtown, stadiums & parks
★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants!
Fridge, microwave, oven, stovetop

★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants!

10.0 out of 10, Exceptional, (22)
"The property host was very responsive, good location and functioning apartment. Our stay was great, and we enjoyed every bit of our time. "
The price is AU$551
includes taxes & fees
13 Jan - 14 Jan 2025
★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants!
2 Bedroom/ 2 Bath- 5 mins to stadiums - BEST city views - Free parking!
Smart TV, books

2 Bedroom/ 2 Bath- 5 mins to stadiums - BEST city views - Free parking!

9.4 out of 10, Exceptional, (39)
"Overall a great experience. Was clean and comfortable and had a several nice things done by the owner including ice, a bottle of wine and coffee. We used everything except the ice. Fantastic views of downtown and the rivers. Would stay again but probably not the best place for those who are older or adverse to stairs. Nice little coffee shop down the nearby stairs. Close to stadiums and North side scene. "
2 Bedroom/ 2 Bath- 5 mins to stadiums - BEST city views - Free parking!
Private Vacation Home with large Hot Tub and Fire Pit -- Sleeps 18
Exterior

Private Vacation Home with large Hot Tub and Fire Pit -- Sleeps 18

10.0 out of 10, Exceptional, (10)
"We rented this house for a get together as an anniversary gift "
Private Vacation Home with large Hot Tub and Fire Pit -- Sleeps 18
Pet-Friendly Apollo Home w/ Furnished Deck!
Interior

Pet-Friendly Apollo Home w/ Furnished Deck!

9.0 out of 10, Wonderful, (8)
"Traveling for a wedding, our family decided to be together. It was wonderful. This was a perfect home for the 10 of us. The home is very spacious w everything you need. Communication w the owner was simple and prompt. Location was peaceful & the neighborhood appeared safe. Thank you for contributing to some wonderful memories! . "
Pet-Friendly Apollo Home w/ Furnished Deck!
Pet-Friendly Home - 100 Feet to Walnut Street
Outdoor dining

Pet-Friendly Home - 100 Feet to Walnut Street

10.0 out of 10, Exceptional, (25)
"We had a lovely stay. When staying with dogs it is good to note that there is no grass in the yard or close by to take them out easily. The gate on the back yard fence does not latch so you can’t let dogs loose in the yard safely to play. Otherwise the apartment is exactly how it is described."
Pet-Friendly Home - 100 Feet to Walnut Street
Family and 🐕 friendly☆3BR house☆Porch swing☆Mars☆PGH☆Cranberry
Fridge, microwave, oven, stovetop

Family and 🐕 friendly☆3BR house☆Porch swing☆Mars☆PGH☆Cranberry

10.0 out of 10, Exceptional, (16)
"Laurel was an excellent host. The property was just like in the pictures. Ver clean, nice bed, clean comfortable furniture. We truly fellt that we were home. location is perfectly centered from shopping bars and restaurants. when I come back to “The Burgh” I will be looking for this property."
Family and 🐕 friendly☆3BR house☆Porch swing☆Mars☆PGH☆Cranberry
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
Exterior

Kasa South Side Pittsburgh

4.0 star property
8.6 out of 10, Excellent, (70)
"An excellent hotel for an excellent price! The hotel consists of units in an apartment building which have been purchased by the hotel company. Overall the units are very nice and spacious, with a full kitchen in unit. I stay here whenever I visit Pittsburgh!"
Kasa South Side Pittsburgh
Breathtaking Spacious PGH Skyline Loft On Carson Street
Outdoor dining

Breathtaking Spacious PGH Skyline Loft On Carson Street

8.6 out of 10, Excellent, (25)
"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
❤️Cozy Townhome on Carey with Private Deck Space ❤️
Exterior

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (22)
"Property was as advertised. Clean, Great location. Had the kitchen items we needed. Plenty of room for all. Worked well for 4 of us. Beds could have been a little more comfortable on the main level. Upper level beds comfortable. Lots of stairs. But most South side flat properties will have lots of stairs. Location made up for all of that and we were satisfied. The host communicated perfectly, timely and met our needs.Clean property. Definitely worth what we paid for it. Mike"
The price is AU$407
includes taxes & fees
1 Jan - 2 Jan 2025
❤️Cozy Townhome on Carey with Private Deck Space ❤️
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.