Holiday Rentals in South Side

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Holiday Rentals 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 €252
includes taxes & fees
2 Dec - 3 Dec
❤️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

Exquisite 4Bed/3.5Bath Home W/Garage +Rooftop Deck

9.2 out of 10, Wonderful, (29)
"We had a really nice stay. The view of the city was beautiful from the rooftop deck. There are plenty of walkable restaurants and coffee shops. The property was very clean. The parking is a little tricky with the one car garage with an SUV. Would stay there again. "
Exquisite 4Bed/3.5Bath Home W/Garage +Rooftop Deck

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

9.6 out of 10, Exceptional, (28)
"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!

Stay Pittsburgh

2.0 star property
7.6 out of 10, Good, (83)
"It was def worth the price you pay to stay "
The price is €100
includes taxes & fees
10 Dec - 11 Dec
Stay Pittsburgh

The Warhola Bloomfield

4.5 star property
5.0 out of 10, (20)
"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 price is €120
includes taxes & fees
2 Dec - 3 Dec
The Warhola Bloomfield

Abode Pittsburgh - Downtown Convention Center

3.5 star property
7.4 out of 10, Good, (71)
"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 €153
includes taxes & fees
2 Dec - 3 Dec
Abode Pittsburgh - Downtown Convention Center

🏰Warren Castle🏰 - Breathtaking Views of Pittsburgh 💙

9.8 out of 10, Exceptional, (37)
"This place was beautiful, clean, had off street parking which was amazing. My friend wanted it to be her real apartment it was so nice. It was a short stay and I appreciated the availability of that. If I stay in Pittsburgh again I would definitely stay at this location again. Honestly if I could have been there longer I would have."
The price is €225
includes taxes & fees
2 Dec - 3 Dec
🏰Warren Castle🏰 - Breathtaking Views of Pittsburgh 💙

Not so tiny house with full kitchen & patio swing

9.6 out of 10, Exceptional, (37)
"I loved this little spot... I did a solo getaway, and this was perfect for me. In a pretty quiet neighborhood, and I felt safe. Close to all the good stuff Pittsburgh has to offer. I will be back!"
The price is €189
includes taxes & fees
2 Dec - 3 Dec
Not so tiny house with full kitchen & patio swing

The Elliott Hotel at Highland Park

5.0 star property
4.0 out of 10, (20)
"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 Elliott Hotel at Highland Park

Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet

9.4 out of 10, Exceptional, (136)
"Very cute house on a dead end street, tucked away on the ridge in the woods, just a few minutes from downtown Carnegie. The house is very quirky but a lovely stay that feels private and easy to access all the things you’ll want from your stay in Pittsburgh!"
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet

Stylish 4Bdr Loft Home, North Shore, City Skyline

10.0 out of 10, Exceptional, (22)
"Pleasant stay. House is comfortable, clean. Photos accurate. Host accessible."
The price is €475
includes taxes & fees
2 Dec - 3 Dec
Stylish 4Bdr Loft Home, North Shore, City Skyline

House in the mountains with spectacular views of the Waterfront and Monogahala!

The price is €252
includes taxes & fees
28 Nov - 29 Nov
House in the mountains with spectacular views of the Waterfront and Monogahala!

Entire Pittsburgh-Carnegie 4Bdr, 2Bath Home King Bed, FreeParking,Patio & Porch!

7.2 out of 10, Good, (7)
"It was spacious, good location and clean. Nice Neighborhood. Would recommend it. We will use it again."
The price is €336
includes taxes & fees
2 Dec - 3 Dec
Entire Pittsburgh-Carnegie 4Bdr, 2Bath Home King Bed, FreeParking,Patio & Porch!

Shadyside Penthouse

6.6 out of 10, (7)
"This place has lots of room- four large bedrooms in addition to a living room and kitchen. Great communication with the host and convenient to Pitt, CMU, and shopping. A great rental for a large group!"
Shadyside Penthouse

Spacious Downtown Loft | Free Parking | Gym

9.6 out of 10, Exceptional, (18)
"Host responds the next day. Wifi modem is in another unit. Lovely pad. Will stay again IF TV & WIFI situation & communication speed is fixed. "
The price is €246
includes taxes & fees
28 Nov - 29 Nov
Spacious Downtown Loft | Free Parking | Gym

🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft

9.8 out of 10, Exceptional, (39)
"The property was conveniently located near the convention center which is where my business was. It was clean and well-kept. The valet service was excellent. Great property!"
🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft

Comfortable private unit with hot tub and free parking

10.0 out of 10, Exceptional, (38)
"Wonderful place will definitely use it again in future if needed thank you "
The price is €183
includes taxes & fees
2 Dec - 3 Dec
Comfortable private unit with hot tub and free parking

CozySuites at First Avenue

3.0 star property
8.4 out of 10, Very good, (11)
"SO nice! Clean and updated….excellent parking!"
CozySuites at First Avenue
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

HYATT house Pittsburgh-South Side

3.0 star property
8.8 out of 10, Excellent, (1112)
"Everything was great except for one thing , we had booked online, then decided to stay a couple extra days the website would not let me add on the days without it, charging an astronomical price. It was cheaper to make two reservations. Loved location."
The price is €155
includes taxes & fees
1 Dec - 2 Dec
HYATT house Pittsburgh-South Side

Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel

2.5 star property
7.2 out of 10, Good, (1109)
"Service was good. Staff was helpful and professional. Linens seemed clean and bedding was comfortable. Room was in need of some general maintenance. Paint, wallpaper, grout and caulking needs replaced or repaired. This hotel has potential to be 5 star with some attention to details."
The price is €98
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel

Wyndham Grand Pittsburgh Downtown

3.5 star property
7.8 out of 10, Good, (2985)
"Staff friendly, good price, nice hotel, central location "
The price is €156
includes taxes & fees
28 Nov - 29 Nov
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.

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.