South Side Vacation Rentals

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Vacation Rentals in South Side

Kasa South Side Pittsburgh
Exterior
Kasa South Side Pittsburgh
4.0 star property
8.8 out of 10, Excellent, (56)
"Much more like a home than a hotel room!"
Kasa South Side Pittsburgh
Breathtaking Spacious PGH Skyline Loft On Carson Street
Property grounds
Breathtaking Spacious PGH Skyline Loft On Carson Street
8.6 out of 10, Excellent, (17)
"The property was great! The top patio was excellent. Spent a lot of time up there. Beautiful view of city and surrounding area. Easy Uber to penguins game. Right there in the middle of the Carson Street entertainment."
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 ❤️
8.8 out of 10, Excellent, (18)
"Pros: Property was neat and tidey for most part. Nicely decorated to make it homey-vibe. Bathroom was very nicely remodeled, (shower kind of small if you’re a plus sized person) Great location off of Carson Street, able to walk to a lot from this location. Keyless entry was a breeze. All information was emailed in appropriate time of check in. Cute little area of coffee/laundry items provided in kitchenette area. Complimentary bathroom items also included in case you forget an item. Cons: 1...
The price is ￥7,882
per night
Jun 3 - Jun 4
❤️Cozy Townhome on Carey with Private Deck Space ❤️
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Exquisite 4Bed/3.5Bath Home W/Garage +Rooftop Deck
Fridge, microwave, oven, stovetop
Exquisite 4Bed/3.5Bath Home W/Garage +Rooftop Deck
9.4 out of 10, Exceptional, (26)
"Very easy to find and it was nice to have a garage and parking spot. We were able to find close by street parking for our 3rd car and friends that came over. The property was clean and had everything we needed. The backyard with grill was nice for our dog and another outdoor space. There is a busy road and train tracks behind the property, we thought it would be a problem but we dealt with it and got use to the train. Beds were comfortable but would not recommend the futons on the 3rd floor for...
Exquisite 4Bed/3.5Bath Home W/Garage +Rooftop Deck
City view home in South Side, Pittsburgh!
Exterior
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!
The Schenley! 8 Bed/5 bath! Sleeps 22! 4 x Free Parking!
Fridge, microwave, oven, stovetop
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
Marina
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
Traditional Apartment 4F | City view
Stay Pittsburgh
2.0 star property
7.6 out of 10, Good, (48)
"For having 6 kids this was perfect. Walked to the concert at PPG. Great price! "
The price is ￥16,981
per night
Jun 12 - Jun 13
Stay Pittsburgh
Abode Pittsburgh - Downtown Convention Center
Interior
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 ￥12,138
per night
Jun 3 - Jun 4
Abode Pittsburgh - Downtown Convention Center
The Elliott Hotel at Highland Park
Luxury Apartment, 1 Bedroom | Living area | 55-inch Smart TV with cable channels, Netflix, Hulu
The Elliott Hotel at Highland Park
5.0 star property
5.2 out of 10, (9)
"Beautiful vintage property that has been updated and close to everything but still very quiet and private! "
The price is ￥10,429
per night
Jun 2 - Jun 3
The Elliott Hotel at Highland Park
CozySuites at First Avenue
Studio | Private kitchen | Fridge, microwave, oven, stovetop
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
The Warhola Bloomfield
Luxury Apartment | Private kitchen | Full-size fridge, microwave, oven, dishwasher
The Warhola Bloomfield
4.5 star property
6.0 out of 10, (6)
"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 ￥14,562
per night
Jun 20 - Jun 21
The Warhola Bloomfield
Luxe Highland Park Apt | The Elliott Mansion
1 bedroom, desk, iron/ironing board, travel crib
Luxe Highland Park Apt | The Elliott Mansion
7.2 out of 10, Good, (11)
"We enjoyed our stay!"
The price is ￥9,616
per night
Jun 2 - Jun 3
Luxe Highland Park Apt | The Elliott Mansion
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
Property grounds
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
9.6 out of 10, Exceptional, (121)
"Our stay was to help our son who is moving to the area with home renovations. We didn't spend much time at the house other than coming home at the end of the day and cleaning up. It was nice that we could bring our dog, and we felt comfortable in the space with him. The weather was rainy, but the back porch looked like a great space to hang out if it had been nicer."
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
Spacious Downtown Loft | Free Parking | Gym
Fridge, microwave, oven, stovetop
Spacious Downtown Loft | Free Parking | Gym
10.0 out of 10, Exceptional, (3)
"Overall, I had a wonderful stay. I plan to rent from this renter the next time I am in town. This is just an FYI if my issue happens to someone else. Please contact the renter right away with any issues. The only issue was the 1st night I arrived at 11:30 pm. The orginal apartment that I rented wasn't cleaned. I emailed the renter and received a new apartment within 6 minutes. I was happy with the quick speed of response time and ability to move me to a different apartment considering...
The price is ￥15,409
per night
Jun 3 - Jun 4
Spacious Downtown Loft | Free Parking | Gym
CozySuites Downtown Pittsburgh
Deluxe Apartment, 2 Bedrooms | Desk, laptop workspace, iron/ironing board, free WiFi
CozySuites Downtown Pittsburgh
3.5 star property
CozySuites Downtown Pittsburgh
Shadyside Penthouse
4 bedrooms, iron/ironing board, WiFi, bed sheets
Shadyside Penthouse
10.0 out of 10, Exceptional, (1)
"If you have a big family this property is wonderful. The owner is easy to get a hold of an very nice. I highly recommend this property"
Shadyside Penthouse
🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft
Fridge, microwave, oven, stovetop
🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft
10.0 out of 10, Exceptional, (24)
"Very impressive property: the building is in a nice location with safe entry and car valet, well maintained unit with great views, and friendly responsive host."
🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft
2 King Beds / Free Parking / Arcade / Patio
Property grounds
2 King Beds / Free Parking / Arcade / Patio
9.8 out of 10, Exceptional, (9)
"Hi"
The price is ￥19,654
per night
Jun 18 - Jun 19
2 King Beds / Free Parking / Arcade / Patio
Modern Meditation 2 Bedroom Apartment
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Modern Meditation 2 Bedroom Apartment
9.4 out of 10, Exceptional, (9)
"It was a pleasant stay. The place was very nice. Was much better than staying in a hotel."
Modern Meditation 2 Bedroom Apartment
Don't see what you're looking for?
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
Exterior
Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
2.5 star property
7.2 out of 10, Good, (1002)
"Convienent. Safe. 2 bits of feedback- bed was STIFF and pool was slippery. Both of us nearly fell"
The price is ￥15,945
per night
Jun 2 - Jun 3
Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
HYATT house Pittsburgh-South Side
Sports facility
HYATT house Pittsburgh-South Side
3.0 star property
8.8 out of 10, Excellent, (1001)
"This was a great venue for a family wedding! The suites are large and comfortable."
The price is ￥22,000
per night
Jun 16 - Jun 17
HYATT house Pittsburgh-South Side
Wyndham Grand Pittsburgh Downtown
Exterior
Wyndham Grand Pittsburgh Downtown
3.5 star property
7.6 out of 10, Good, (2725)
"Great hotel. Bring an extra pillow!"
The price is ￥24,665
per night
Jun 16 - Jun 17
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.

Search for holiday rentals in South Side on Expedia! You can easily find your home rentals, villas, holiday apartments in South Side using one of the methods below:

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Look no further and take a look at our great range of rental properties in South Side!

Frequently asked questions

Are there vacation rentals in South Side?

Yes, you can find vacation rentals close to top attractions in South Side, or you can go with a more remote option if you'd like a relaxing place to stay. Our travelers say South Side has a good selection of lively bars and top-notch restaurants. The theater scene and live music are some other things you might like to check out during your trip.

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

Convenient Getaway : This South Side vacation home rental 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 favorite 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 vacation rentals will I find in South Side?

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

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 like PPG Paints Arena and Acrisure Stadium.

What are vacation rentals like in South Side?

Vacation rentals are privately owned properties you can stay in for a couple days or more in South Side. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips.

Recent reviews of South Side properties
Expedia verified reviews

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

5/5 Excellent
"Great hotel. Bring an extra pillow!"
A verified traveler stayed at Wyndham Grand Pittsburgh Downtown
Posted 21 hours ago
Wyndham Grand Pittsburgh Downtown