South Side Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for South Side holiday rentals

A compact kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dishwasher.

1. Carey Way Quarters - Explorer's Dream Pad

South Side Flats

HK$1,403 total

includes taxes & fees

7 Nov - 8 Nov

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with wicker chairs and a round table.

2. 2615 Jane Down - Southside

South Side Flats

Bertha T.

HK$1,556 total

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with a brick wall, white bar stools, and a dining area with a grey sofa.

3. Cozy&Modern 2Bdr Apt PIttsburgh

South Side Flats

Abby S.

HK$1,206 total

includes taxes & fees

15 Oct - 16 Oct

A modern living room with a sectional sofa, a dark coffee table, and a world map on the wall.

4. Iron City of South Side Flats Charming 2-bedroom Unit

South Side Flats

Manuel M.

HK$2,182 total

includes taxes & fees

21 Oct - 22 Oct

5. Steel City of South Side Flats Charming 2-Bedroom Unit

South Side Flats

Heather B.

HK$2,206 total

includes taxes & fees

21 Oct - 22 Oct

A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

6. Carey Way Quarters – Modern 2BR Near Carson Street

South Side Flats

Corey E.

HK$1,810 total

includes taxes & fees

7 Nov - 8 Nov

A bedroom with a bed, two pillows, a wall-mounted sign, and a window with blinds.

7. Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi

South Side Slopes

HK$1,580 total

includes taxes & fees

8 Nov - 9 Nov

An outdoor dining area with a wooden table and black chairs, surrounded by string lights and a white pergola.

8. Pittsburgh Pennsylvania house

South Side Flats

Adrian C.

HK$2,037 total

includes taxes & fees

3 Nov - 4 Nov

A living room with a green sofa, a glass coffee table, a TV mounted on the wall, and a sliding barn door.

9. Cozy Centralized 3bd 2bath House w/ Free Parking

South Side Flats

Mark W.

HK$3,311 total

includes taxes & fees

19 Oct - 20 Oct

A dining area with a round table, white chairs, a hanging light fixture, a radiator, and a colorful cityscape painting on the wall.

10. 3-bedroom house in Southside Flats neighborhood of Pittsburgh.

South Side Flats

Kyle S.

HK$1,802 total

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with white cabinets, a stainless steel dishwasher, a microwave, and a black countertop.

11. Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

Allentown

John

HK$2,273 total

includes taxes & fees

15 Oct - 16 Oct

An outdoor deck with a fire feature, seating, and a view of the city at night.

12. City Skyline - Outside decks - Contemporary

South Side Slopes

Mary H.

A rustic bar area with wooden walls, two stools, a barrel, and a hanging light fixture.

13. The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!

South Side Flats

Alyssa B.

HK$2,319 total

includes taxes & fees

7 Nov - 8 Nov

A neatly made bed with a unique towel arrangement, a headboard, and a decorative wall piece.

14. Historic Gem Heart of Southside-Sleeps 10

South Side Flats

hans e.

HK$2,531 total

includes taxes & fees

19 Oct - 20 Oct

A row of brick townhouses with front porches, a small garden, and a visible mailbox.

15. Central 5BD Getaway - Spacious Home w/ BBQ

South Side Flats

Sean O.

A living room with a fireplace, a television, and a dining area with a table and chairs.

16. HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

South Side Flats

Butch K.

HK$1,609 total

includes taxes & fees

9 Nov - 10 Nov

A kitchen with wooden cabinets, a dining table with a floral tablecloth, and a glass of wine.

17. Carey Way Quarters – Stylish 3-Bedroom Loft!

South Side Flats

Kirk h.

HK$2,055 total

includes taxes & fees

6 Nov - 7 Nov

A wooden deck with potted plants and a hanging fern.

18. Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

South Side Flats

Kevin M.

HK$6,774 total

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a central island with a basket of decorative items.

19. Clean and comfortable 3BR home in the South Side neighborhood

South Side Slopes

Amanda R.

A modern kitchen with grey cabinets, a stainless steel dishwasher, a microwave, and wooden shelves with decorative items.

20. Industrial Chic Studio-Modern Comfort in the Burgh

South Side Flats

Rich D.

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Top South Side Hotel Reviews

DoubleTree by Hilton Pittsburgh - Green Tree

10/10 Excellent

"Everything was great! The only minor bump in the road was check in. There was a long line, but they moved as quickly as they could."

Placemakr Downtown Pittsburgh at The Pennsylvanian

10/10 Excellent

"The architecture was so unique. Very special and all on its own, worth the stay. But on top of that the staff was one and all pleasant and went out of their way to help us by buzzing us in and holding doors as we maneuvered bicycles to our room. They offered restaurant recommendations and directions to get there. We were always greeted pleasantly and wished a good day on our way out. The in room coffee had 2 decaf pods which is unusual. Also there was an herbal and green tea option as well. The whole suite was very comfortable. The high ceilings are so lovely. Thankfully they had vending machines with meals not just snacks as we arrived very late and had not been able to stop so it was 11:30 pm when we got food. The only downsides were traffic noise and musty odor in the bathroom initially. I highly recommend this hotel."

Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent

"Amazing hotel friendly staff very helpful and valet was fast and easy. Loved the Hot tub but wish it was open later as well as evening amenities like the adult beverages and horderves due to going to a Concert we missed out on those perks of the hotel. We did get up early to be able to enjoy the amazing breakfast, and enjoyed the hot tub and pool before we headed out to see the city views, they held out luggage so we didn't have to get the car just to repark it. 10/10 would stay again love the area and how close it is to ppg and the wylie,"

Joinery Hotel Pittsburgh, Curio Collection by Hilton

8/10 Good

"We appreciated the central location of the Joinery and the historic red brick building built in 1924. The area isn’t the liveliest, but it is downtown and a 15-minute walk to the Cultural District and the Sixth Street Bridge. Our room was small, but had most of the amenities, including a big flatscreen TV, coat rack, safe, small fridge, coffee maker with coffee and tea pods, steamer, hair dryer, telephone, toiletries, and in-room temperature control. The towels were fairly soft. The bed was comfortable with a pillowtop mattress and down pillows. Storage space was lacking. The hotel has free wi-fi, a bar, coffee bar, restaurant, paid parking, a small gift shop with Pittsburgh themed gifts, and is pet friendly. The lobby is attractive and features art by Pittsburgh artists, vinyl records, and places to hang out. There’s also a microwave guests can use, small snacks available for purchase, ice machines, and a gym. If you take the stairs, you wind up going through housekeeping and employee areas. The staircases were dirty and smelly, but it felt like they didn’t expect guests to ever take the stairs. No one cleaned our room, which was definitely strange. When we first entered our room, it wasn’t cleaned well. There was a towel on the floor and the headboard was dusty, For the price, I felt they could have been more generous by providing drinking water, pens, a pad of paper, etc. However, you can check your bags in for free. Service was friendly at all times."

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Side holiday rentals

1. Carey Way Quarters - Explorer's Dream Pad

2. 2615 Jane Down - Southside

3. Cozy&Modern 2Bdr Apt PIttsburgh

4. Iron City of South Side Flats Charming 2-bedroom Unit

5. Steel City of South Side Flats Charming 2-Bedroom Unit

6. Carey Way Quarters – Modern 2BR Near Carson Street

7. Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi

8. Pittsburgh Pennsylvania house

9. Cozy Centralized 3bd 2bath House w/ Free Parking

10. 3-bedroom house in Southside Flats neighborhood of Pittsburgh.

11. Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

12. City Skyline - Outside decks - Contemporary

13. The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!

14. Historic Gem Heart of Southside-Sleeps 10

15. Central 5BD Getaway - Spacious Home w/ BBQ

16. HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

17. Carey Way Quarters – Stylish 3-Bedroom Loft!

18. Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

19. Clean and comfortable 3BR home in the South Side neighborhood

20. Industrial Chic Studio-Modern Comfort in the Burgh

Find holiday rentals that suit your style

Top South Side Hotel Reviews

DoubleTree by Hilton Pittsburgh - Green Tree

TRYP by Wyndham Pittsburgh/Lawrenceville

Placemakr Downtown Pittsburgh at The Pennsylvanian

Hilton Garden Inn Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown

Holiday Inn Express & Suites Pittsburgh West - Greentree by IHG

The Landing Hotel at Rivers Casino

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Omni William Penn Hotel

Find out more about South Side

Explore a world of travel with Expedia

Go further with the Expedia app

South Side Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for South Side holiday rentals

1. Carey Way Quarters - Explorer's Dream Pad

2. 2615 Jane Down - Southside

3. Cozy&Modern 2Bdr Apt PIttsburgh

4. Iron City of South Side Flats Charming 2-bedroom Unit

5. Steel City of South Side Flats Charming 2-Bedroom Unit

6. Carey Way Quarters – Modern 2BR Near Carson Street

7. Stylish South Side Retreat | Free Parking | 2 Baths | Fast WiFi

8. Pittsburgh Pennsylvania house

9. Cozy Centralized 3bd 2bath House w/ Free Parking

10. 3-bedroom house in Southside Flats neighborhood of Pittsburgh.

11. Pittsburgh’s Newest Jacuzzi & Fire Pit Urban Lodge

12. City Skyline - Outside decks - Contemporary

13. The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!

14. *Historic Gem* Heart of Southside-Sleeps 10

15. Central 5BD Getaway - Spacious Home w/ BBQ

16. HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

17. Carey Way Quarters – Stylish 3-Bedroom Loft!

18. Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces

19. Clean and comfortable 3BR home in the South Side neighborhood

20. Industrial Chic Studio-Modern Comfort in the Burgh

Find holiday rentals that suit your style

Top South Side Hotel Reviews

DoubleTree by Hilton Pittsburgh - Green Tree

Find out more about South Side

Explore a world of travel with Expedia

Go further with the Expedia app

14. Historic Gem Heart of Southside-Sleeps 10