South Side Holiday Rentals

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Holiday Rentals in South Side

Kasa South Side Pittsburgh
4.0 star property
8.8 out of 10, Excellent, (57)
"Directions regarding parking were at times confusing...counter tops were sticky...had to clean before using...otherwise everything was as expected"
Kasa South Side Pittsburgh
Exquisite 4Bed/3.5Bath Home W/Garage +Rooftop Deck
9.4 out of 10, Exceptional, (27)
"We came to visit our son and our daughter and her husband. it was so wonderful to be able to include our dogs in the weekend. The house allowed plenty of space for us to all spread out and the fenced in yard was incredible for our dogs. While not the most beautiful neighborhood it was well located for easy access to all the places we wanted to visit in Pittsburgh. We would come again. Thanks!"
Exquisite 4Bed/3.5Bath Home W/Garage +Rooftop Deck
City view home in South Side, Pittsburgh!
9.2 out of 10, Wonderful, (5)
"Once we became acclimated to the terrain & most convenient roads to reach the destination, it was pretty easy to get around. The house provided sufficient space for our small group. The only thing was the lack of AC to keep us cool. Only one room fan and a small ceiling fan upstairs. Our last night was a bit WARM & a little sweaty. The house was clean. Overall, we enjoyed our stay."
City view home in South Side, Pittsburgh!
❤️Cozy Townhome on Carey with Private Deck Space ❤️
9.0 out of 10, Wonderful, (19)
"Amazing Place very clean very nice close to everything Host will most definitely will be booking again soon"
The price is NZ$409
per night
24 Jun - 25 Jun
❤️Cozy Townhome on Carey with Private Deck Space ❤️
The Schenley! 8 Bed/5 bath! Sleeps 22! 4 x Free Parking!
9.6 out of 10, Exceptional, (24)
"The Schenley is a MUST for a large family gathering. We had four families with a total of 13 people fit comfortably inside the three apartments with several empty beds available for our daughter’s college friends that crashed for an evening or two. It is in a great location in the Southside Flats just walking distance to lots of great restaurants and bars. We easily walked to Fat Heads Saloon, Hofbrauhaus, and the Tiki Bar for lunch, dinner, and drinks, respectively. Each apartment is fully...
The Schenley! 8 Bed/5 bath! Sleeps 22! 4 x Free Parking!
House overlooking City Skyline, River and Bridges
10.0 out of 10, Exceptional, (25)
"This wonderful old home is located in a time capsule neighborhood. It gives a sense of what life was like in the early days of Pittsburgh."
House overlooking City Skyline, River and Bridges
Stay Pittsburgh
2.0 star property
7.6 out of 10, Good, (50)
"For having 6 kids this was perfect. Walked to the concert at PPG. Great price! "
The price is NZ$148
per night
26 Jun - 27 Jun
Stay Pittsburgh
Abode Pittsburgh - Downtown Convention Center
3.5 star property
7.0 out of 10, Good, (55)
"At night the property was very quiet, and the people that we encountered were very friendly👍"
The price is NZ$340
per night
24 Jun - 25 Jun
Abode Pittsburgh - Downtown Convention Center
CozySuites at First Avenue
3.0 star property
8.0 out of 10, Very good, (6)
"Clean, good communication, convenient location and parking! Would book again!"
CozySuites at First Avenue
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
9.6 out of 10, Exceptional, (123)
"Many places advertise they are dog-friendly but really just mean they allow your dogs to accompany you; the Carnegie Cottage truly welcomes your pups. Dog bowls were waiting with a little welcome treat as well as a blanket and toys for them. The patio also had a lead so they could explore the yard freely. As this is a typical Pittsburgh house ( I would know since I grew up very close to here), a senior dog may have an issue with the steepness of the steps but my 13 year old boxer did fine as...
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft
10.0 out of 10, Exceptional, (25)
"Space had everything we needed and the location was amazing we were able to walk everywhere. Valet parking was included which was a plus. Also able to use the Community room and 3rd floor roof patio with outdoor seating. Recommend this location and space. We walked to the Art Festival and to the Stadium."
🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft
CozySuites Downtown Pittsburgh
3.5 star property
10.0 out of 10, Exceptional, (1)
"What a spectacular property. After a 30 hour travel time it was the most beautiful apartment to come home to. Beautiful furnishings, wonderful view of the Pittsburgh cityscape, and just overall such a premium, luxurious feel. The beds were a pleasure to sleep on, the bathrooms were more luxurious than some 5 star hotels, and it had everything we needed. Every time I thought to myself, "I could use ", it was there in the apartment. The only thing missing was a tea bag! And for that to be the...
CozySuites Downtown Pittsburgh
The Elliott Hotel at Highland Park
5.0 star property
5.6 out of 10, (10)
"The host Sofia was very knowledgeable! She knows her stuff!! What I needed, where I had to go, local spots. .. you name it, she new it & more"
The price is NZ$415
per night
3 Jul - 4 Jul
The Elliott Hotel at Highland Park
The Warhola Bloomfield
4.5 star property
6.6 out of 10, (7)
"It was so wonderful I felt like staying at home. The community was beautiful. The atmosphere was great easy to go to any places in the city to go eat dance drink didn’t take long to get there just overall wonderful."
The price is NZ$242
per night
25 Jun - 26 Jun
The Warhola Bloomfield
2 King Beds / Free Parking / Arcade / Patio
9.8 out of 10, Exceptional, (10)
"We came to see a ballgame and stayed in town for 2 days. The house was conveniently located a short distance from local sights, bars and restaurants, with parking on the street in front. Three roomy bedrooms each with their own bath, the comfiest beds and large screen tv mounted on the wall Beautifully decorated with a well appointed kitchen with everything you need if you want to cook while there. And everything spotlessly clean! We enjoyed cool evenings and morning coffee on the back deck....
2 King Beds / Free Parking / Arcade / Patio
Luxury TownHome 4Bedroom3Bath 2 Car Garage Sleeps 10 NearDowntown,Stadium&Casino
9.8 out of 10, Exceptional, (26)
"Our group of 5 in town for a Pirates game enjoyed the place very much. Clean as a whistle, comfortable, stadium and downtown area easily walkable. We did little more there than lay our heads, but it was just what we needed. Max's Allegheny Tavern less than 100 yards away was an unexpected bonus, as was Verdetto's a short walk across the bridge over the interstate. Would definitely stay there again."
The price is NZ$736
per night
9 Jul - 10 Jul
Luxury TownHome 4Bedroom3Bath 2 Car Garage Sleeps 10 NearDowntown,Stadium&Casino
Shadyside Penthouse
7.4 out of 10, Good, (3)
"VRBO is outside of the downtown area, but easy to get to everything. Very easy to find and comfortable place for our group of 9. Carmine was very responsive. I proved to be a bit needy when I left my laptop behind and got panicky and had to have it FedEx'd to me. Easy to park near a transit station and use the T to get around as well. Loved it and would definitely stay here again."
Shadyside Penthouse
Luxe Highland Park Apt | The Elliott Mansion
7.2 out of 10, Good, (13)
"This home is absolutely gorgeous. There is an allure when you 1st enter and navigate the 4 set stairwell where you begin to have a doubt as the 90 degree summer heat hits you but let me tell you, when you get to your door and press the code in and enter the apartment it is ABSOLUTE DIVINITY! The 1 bedroom apartment is EXACTLY as listed and the breezy cool brand new AC Units are like a breath of fresh air. My wife and I enjoyed this cozy little apartment so much. The shower is kind of wildly fun...
The price is NZ$235
per night
3 Jul - 4 Jul
Luxe Highland Park Apt | The Elliott Mansion
🏰Spacious Vacation Home 4 BR W/ 2 Master Suites, 🏋🏻‍♀️Gym, and Game Room🏀
9.8 out of 10, Exceptional, (27)
"Thank you for the wonderful stay in your beautiful house. The kitchen is fantastic. The bedrooms were spacious. Lovely decor."
🏰Spacious Vacation Home 4 BR W/ 2 Master Suites, 🏋🏻‍♀️Gym, and Game Room🏀
Not so tiny house with full kitchen & patio swing
9.6 out of 10, Exceptional, (30)
"The not so tiny house was great! Very great location for walking to local attractions."
The price is NZ$337
per night
28 Jun - 29 Jun
Not so tiny house with full kitchen & patio swing
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See all available properties in South Side
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.

Other types of properties in South Side you may be interested in

Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
2.5 star property
7.0 out of 10, Good, (1001)
"Magnificent size and breakfast foods were nicely done. Comfortable bed and more than enough power outlets. Staff very professional. "
The price is NZ$162
per night
23 Jun - 24 Jun
Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
HYATT house Pittsburgh-South Side
3.0 star property
8.8 out of 10, Excellent, (1004)
"The view by the river was really nice! The staff was very friendly to us on check in. She answered all my questions and took time to explain to me everything. I will come back to Hyatt house again, definitely!"
The price is NZ$267
per night
23 Jun - 24 Jun
HYATT house Pittsburgh-South Side
Wyndham Grand Pittsburgh Downtown
3.5 star property
7.6 out of 10, Good, (2732)
"The bathtub was extremely slippery. There should be a rubber mat or some kind of adhesive strips inside the tub to prevent a fall while standing. Apart from that complaint, we enjoyed our stay. "
The price is NZ$281
per night
14 Jul - 15 Jul
Wyndham Grand Pittsburgh 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our South Side holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up South Side. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in South Side. Seeing all the best attractions is bound to make you fall in love with South Side. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in South Side short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in South Side?

Yes, there are holiday rentals close to the most popular sights in South Side, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say South Side has a good selection of lively bars and top-notch restaurants. The theatre scene and live music are some other things you might like to check out during your trip.

What are some of the best holiday rentals that South Side has to offer?

Convenient Getaway : This highly rated holiday home rental in South Side is equipped with a patio, laundry facilities and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker. Other favourite homes for rent in South Side are Charming 2BD/3BM home w/fireplace/hut tub/private patio and Gorgeous Southside Slopes home with outdoor hot tub and city view!.

How many holiday rentals will I find in South Side?

Choose from 59 Expedia holiday rentals in South Side for a memorable holiday.

What can I see and do in South Side?

Explore the area and family-friendly sights such as Senator John Heinz Regional History Centre, or get out into nature at a spot like PNC Park. While in the area, you can also visit popular places such as PPG Paints Arena and Acrisure Stadium.

What are holiday rentals like in South Side?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Side. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a small group gathering.

Recent reviews of South Side properties
Expedia verified reviews