South Side Holiday Rentals

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Holiday Rentals in South Side

Kasa South Side Pittsburgh

4.0 star property
8.6 out of 10, Excellent, (72)
"We had an amazing stay, unfortunately the only parking was in a parking garage and you get charged anytime your vehicle leaves so we spent a pretty penny just to get to and from. Regardless the room and building itself was nice and clean, we also enjoyed the pool! Definitely recommend!"
Kasa South Side Pittsburgh

The Schenley! 8 Bed/5 bath! Sleeps 22! 4 x Free Parking!

9.8 out of 10, Exceptional, (31)
"After making the reservation, finding out that it was for three separate units was a surprise. It was not an issue but just a surprise."
The Schenley! 8 Bed/5 bath! Sleeps 22! 4 x Free Parking!

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (23)
"We had a lovely stay at the Carey Townhome. Everything was exactly as promised and the location was perfect. There were plenty of bars and restaurants within a 10 minute walk while still being located in a quiet area. Tom was very easy to communicate with as well. I would definitely recommend staying at the Carey Townhome in the future."
The price is AU$396
includes taxes & fees
30 Jan - 31 Jan
❤️Cozy Townhome on Carey with Private Deck Space ❤️

The Josephine Villa by Luxe PGH

3.5 star property
4.0 out of 10, (4)
"Very nice location, great view of the downtown from 4th floor. Plenty of space for the group of 10."
The Josephine Villa by Luxe PGH

Modern Comfort in a Charming Pittsburgh Retreat by Deity Villas

8.4 out of 10, Very good, (6)
"Excellent location very close to the stadium. "
The price is AU$557
includes taxes & fees
30 Jan - 31 Jan
Modern Comfort in a Charming Pittsburgh Retreat by Deity Villas

Breathtaking Spacious PGH Skyline Loft On Carson Street

8.6 out of 10, Excellent, (25)
"Lived the character of the house & neighborhood. Reminded me of home. "
Breathtaking Spacious PGH Skyline Loft On Carson Street

Stay Pittsburgh

2.0 star property
7.6 out of 10, Good, (97)
"The fact it was secured and safe"
The price is AU$166
includes taxes & fees
17 Feb - 18 Feb
Stay Pittsburgh

The Warhola Bloomfield

4.5 star property
5.0 out of 10, (22)
"This place is incredible!! Walking distance to awesome neighborhoods, immaculately clean, comfy furniture and all amenities top-notch! I already want to plan more stays at this spot!!"
The Warhola Bloomfield

Abode Pittsburgh - Downtown Convention Center

3.5 star property
7.6 out of 10, Good, (72)
"Perfect location if you want to experience downtown Pittsburgh. Comfortable and clean. Within walking distance of The Strip and the Train Stop. The only thing that was disappointing was that the windows weren't clean so we couldn't see outside very well. "
The price is AU$258
includes taxes & fees
30 Jan - 31 Jan
Abode Pittsburgh - Downtown Convention Center

2 King Beds / Free Parking / Arcade / Patio

9.8 out of 10, Exceptional, (28)
"Simple check-in, great location, super clean. All around a great stay - would 100% rebook."
The price is AU$465
includes taxes & fees
30 Jan - 31 Jan
2 King Beds / Free Parking / Arcade / Patio

🏰Warren Castle🏰 - Breathtaking Views of Pittsburgh 💙

9.8 out of 10, Exceptional, (40)
"Absolutely no complaints. Great location for us, clean and spacious property. Hosts were excellent communicators. Will be staying here again! "
The price is AU$360
includes taxes & fees
5 Feb - 6 Feb
🏰Warren Castle🏰 - Breathtaking Views of Pittsburgh 💙

Downtown Loft | Skyline Views | Free Parking | Gym

10.0 out of 10, Exceptional, (14)
"wonderful stay, so homey, beautiful view of the city! easy access getting in. host was very nice and responsive when having any questions! 10/10 recommend staying here you will not regret it! "
The price is AU$393
includes taxes & fees
30 Jan - 31 Jan
Downtown Loft | Skyline Views | Free Parking | Gym

Not so tiny house with full kitchen & patio swing

9.6 out of 10, Exceptional, (41)
"very nice modernconvenient only negative which is super minimal, no microwave "
The price is AU$310
includes taxes & fees
30 Jan - 31 Jan
Not so tiny house with full kitchen & patio swing

CozySuites at First Avenue

3.0 star property
8.6 out of 10, Excellent, (14)
"Excellent property "
CozySuites at First Avenue

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!

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

9.8 out of 10, Exceptional, (42)
"Had a great stay. Property was exactly as listed. Very well done. "
The price is AU$641
includes taxes & fees
18 Feb - 19 Feb
Luxurious 4BR Urban Oasis Sleeps 12 Pets OK Private Backyard & 2 Car Garage

Spacious 1-Bedroom Apartment In Pittsburgh (B1)

9.6 out of 10, Exceptional, (19)
"Price, location, facilities, and atmosphere top shelve (for what I needed). "
The price is AU$312
includes taxes & fees
2 Feb - 3 Feb
Spacious 1-Bedroom Apartment In Pittsburgh (B1)

🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft

10.0 out of 10, Exceptional, (42)
"Buddy and I stayed here to catch the last regular season Steeler game. Great location as it's located less than a mile from Acrisure Stadium. Every step counts when there's a 9 windchill. "
🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft

Melwood Suites Unit 107 Studio

2.0 star property
10.0 out of 10, Exceptional, (8)
"Nice big space"
The price is AU$182
includes taxes & fees
2 Feb - 3 Feb
Melwood Suites Unit 107 Studio

Spacious Downtown Loft | Free Parking | Gym

9.6 out of 10, Exceptional, (25)
"If you are looking for somewhere to stay to enjoy a night in Pittsburgh, this is the perfect place to stay! Very close to all local sports arenas and a few fun bars. Very comfy and cozy!"
The price is AU$393
includes taxes & fees
30 Jan - 31 Jan
Spacious Downtown Loft | Free Parking | Gym
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 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
7.2 out of 10, Good, (1002)
"Was in town for an event at the P&G arena. Great location for event as we walked the bridge to and from. Only issue was lots of road work around hotel which made getting into the hotel parking a challenge. "
The price is AU$158
includes taxes & fees
2 Feb - 3 Feb
Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel

Omni William Penn Hotel

4.0 star property
9.0 out of 10, Wonderful, (1394)
"This was the best property that we have stayed at since Covid. "
The price is AU$304
includes taxes & fees
2 Feb - 3 Feb
Omni William Penn Hotel

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4.0 star property
8.2 out of 10, Very good, (1069)
"Great stay and affordable price"
The price is AU$200
includes taxes & fees
4 Feb - 5 Feb
Joinery Hotel Pittsburgh, Curio Collection by Hilton
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.

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.