Title: South Side Vacation Home Rentals from CA $234: Search Top Private Vacation Homes for Rent | Expedia.ca

[South Side Travel Guide](https://expedia.ca/South-Side.dx6343590)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d6343590.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d6343590.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d6343590.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d6343590.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d6343590.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d6343590.Destination-Travel-Guides)

![South Side Flats featuring signage](https://images.trvl-media.com/place/6343589/948a213e-1b75-493e-9fe6-8c5d900ce404.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# South Side Vacation Rentals

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## Check prices for these dates

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for South Side vacation homes

![Interior](https://images.trvl-media.com/lodging/123000000/122780000/122778700/122778621/d83dc43d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, stereo](https://images.trvl-media.com/lodging/123000000/122780000/122778700/122778621/835429a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/123000000/122780000/122778700/122778621/689f5fbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/123000000/122780000/122778700/122778621/4fafaecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 3BR Skyline Retreat w/ Rooftop Deck + Free Parking + Views

[](https://www.expedia.ca/Pittsburgh-Hotels-Modern-3BR-Skyline-Retreat-W-Rooftop-Deck-Free-Parking-Views.h122778621.Hotel-Information)

South Side Slopes

CA $145

CA $427 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Pittsburgh-Hotels-Modern-3BR-Skyline-Retreat-W-Rooftop-Deck-Free-Parking-Views.h122778621.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113640000/113630700/113630660/16c9f495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113640000/113630700/113630660/275fb4d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113640000/113630700/113630660/ef7c91ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113640000/113630700/113630660/a7475201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hot Tub | King Bed | Games | Free Parking

[](https://www.expedia.ca/Pittsburgh-Hotels-Hot-Tub-King-Bed-Free-Parking-Arcade.h113630660.Hotel-Information)

South Side Flats

10/10

Exceptional

(4)

"Perfect vibes for a small girls trip. Great location. Such a fun place, thanks for the small details!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sara P.

CA $193

CA $519 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Pittsburgh-Hotels-Hot-Tub-King-Bed-Free-Parking-Arcade.h113630660.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96970000/96961700/96961617/c908e53f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96970000/96961700/96961617/84ae5f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, offices](https://images.trvl-media.com/lodging/97000000/96970000/96961700/96961617/18ba3244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books, offices](https://images.trvl-media.com/lodging/97000000/96970000/96961700/96961617/cdbd3c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### King Bed | Free Parking | Arcade | Fire Pit

[](https://www.expedia.ca/Pittsburgh-Hotels-King-Bed-Free-Parking-Arcade.h96961617.Hotel-Information)

South Side Flats

10/10

Exceptional

(23)

"Very comfortable"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Deanna

CA $179

CA $502 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Pittsburgh-Hotels-King-Bed-Free-Parking-Arcade.h96961617.Hotel-Information)

![4 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99780000/99777000/99776944/8567eac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99780000/99777000/99776944/25467d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/100000000/99780000/99777000/99776944/2bb31632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99780000/99777000/99776944/ee236d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### City Skyline - Outside decks - Contemporary

[](https://www.expedia.ca/Pittsburgh-Hotels-City-Skyline-Outside-Decks-Contemporary.h99776944.Hotel-Information)

South Side Slopes

10/10

Exceptional

(4)

"our stay was great, the space was everything that was advertised and more. We especially loved the views of Pittsburgh constantly surrounding us. To have the four different porches was astounding. It suited us to hold us for the funeral of my brother which was why we were in Pittsburgh. I would highly recommend this spot for a big group needing a wonderful convenient spot in Pittsburgh. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sandy S.

CA $191

CA $587 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Pittsburgh-Hotels-City-Skyline-Outside-Decks-Contemporary.h99776944.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107830000/107827600/107827506/4329842d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/108000000/107830000/107827600/107827506/968d922c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107830000/107827600/107827506/b598a374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107830000/107827600/107827506/f3927214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### King Bed - BBQ & Hot Tub - Centrally Located

[](https://www.expedia.ca/Pittsburgh-Hotels-3bd-BBQ-Hot-Tub-Centrally-Located.h107827506.Hotel-Information)

South Side Flats

8.0/10

Very good

(2)

"It was an excellent stay and a very accurate property description. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

chad s.

CA $155

CA $495 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Pittsburgh-Hotels-3bd-BBQ-Hot-Tub-Centrally-Located.h107827506.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121510000/121500700/121500638/c06afb7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121510000/121500700/121500638/3ed3a4a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121510000/121500700/121500638/b98d1eb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, stereo](https://images.trvl-media.com/lodging/122000000/121510000/121500700/121500638/03c5fe27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Pittsburgh-Hotels-HostWise-Stays-Southside-Gem-Patio.h121500638.Hotel-Information)

South Side Flats

CA $137

CA $303 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Pittsburgh-Hotels-HostWise-Stays-Southside-Gem-Patio.h121500638.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83570000/83566200/83566134/391c97af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/84000000/83570000/83566200/83566134/bef77efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83570000/83566200/83566134/188ba8b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83570000/83566200/83566134/5509c5e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

[](https://www.expedia.ca/Pittsburgh-Hotels-Carey-Cottage-Cozy-3BR-Stay-In-Of-Southside.h83566134.Hotel-Information)

South Side Flats

7.8/10

Good

(8)

"Home was very comfy children enjoyed there stay I was able to relax and feel comfortable stay I would definitely book again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

bonita f.

CA $69

CA $343 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Pittsburgh-Hotels-Carey-Cottage-Cozy-3BR-Stay-In-Of-Southside.h83566134.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106560000/106550400/106550398/85971f18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106560000/106550400/106550398/933406e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106560000/106550400/106550398/cc867c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106560000/106550400/106550398/c0824973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Central 5BD Getaway - Spacious Home w/ BBQ

[](https://www.expedia.ca/Pittsburgh-Hotels-Central-5BD-Getaway-Spacious-Home-W-BBQ.h106550398.Hotel-Information)

South Side Flats

10/10

Exceptional

(9)

"Great Location and great time. Host was EXTREMELY responsive it was nice "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John L.

[](https://www.expedia.ca/Pittsburgh-Hotels-Central-5BD-Getaway-Spacious-Home-W-BBQ.h106550398.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73040000/73032000/73031981/058c641f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73040000/73032000/73031981/7e4b32a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/74000000/73040000/73032000/73031981/556d27c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/74000000/73040000/73032000/73031981/1cacee3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ❤️Cozy Townhome on Carey with Private Deck Space ❤️

[](https://www.expedia.ca/Pittsburgh-Hotels-Carey-Chateau-A-Luxury-Stay-In-The-South-Side.h73031981.Hotel-Information)

South Side Flats

8.2/10

Very good

(32)

"This house worked excellent for our family to stay for the weekend for college graduation. Perfect location to get around and see South Side."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael P.

CA $69

CA $343 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Pittsburgh-Hotels-Carey-Chateau-A-Luxury-Stay-In-The-South-Side.h73031981.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90020000/90011500/90011428/w2079h1170x0y0-645cff29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90020000/90011500/90011428/a94b7dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, printers](https://images.trvl-media.com/lodging/91000000/90020000/90011500/90011428/6459ce66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/91000000/90020000/90011500/90011428/69a469c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy!

[](https://www.expedia.ca/Pittsburgh-Hotels-Incredible-Views-Perfect-Combination-Of-Luxury-And-Entertainment.h90011428.Hotel-Information)

South Side Slopes

10/10

Exceptional

(14)

"Great stay! Very good location to get to the city and great restaurants. Amazing view! The host was very nice and great to work with. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Eric A.

CA $441

CA $926 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Pittsburgh-Hotels-Incredible-Views-Perfect-Combination-Of-Luxury-And-Entertainment.h90011428.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96760000/96758700/96758626/75602cfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96760000/96758700/96758626/2ecb4620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96760000/96758700/96758626/098112c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/97000000/96760000/96758700/96758626/bd3cd0a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Pittsburgh-Hotels-Big-Dog-Coffees-Little-Red-CatHistoric-Pittsburgh-HomeFREE-Parking-Spaces.h96758626.Hotel-Information)

South Side Flats

10/10

Exceptional

(20)

"Fantastic property. Intriguing history. Great location."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kevin M.

CA $463

CA $855 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Pittsburgh-Hotels-Big-Dog-Coffees-Little-Red-CatHistoric-Pittsburgh-HomeFREE-Parking-Spaces.h96758626.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87370000/87368800/87368723/6357c788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, video games, books, offices](https://images.trvl-media.com/lodging/88000000/87370000/87368800/87368723/06ec18cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87370000/87368800/87368723/859d3fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/88000000/87370000/87368800/87368723/e4fd6eae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### King Bed | Free Parking | BBQ | Fire pit | Arcade

[](https://www.expedia.ca/Pittsburgh-Hotels-Posh-4-Bedroom-On-Carson-St-W-Pro-Cleaning.h87368723.Hotel-Information)

South Side Flats

9.8/10

Exceptional

(66)

"Everything was perfect and we hope to come back again soon. Rank One is ranked #1 in my book. Thanks for a great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joseph M.

CA $137

CA $462 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Pittsburgh-Hotels-Posh-4-Bedroom-On-Carson-St-W-Pro-Cleaning.h87368723.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90190000/90188100/90188001/6a85a529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90188100/90188001/95572498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/90190000/90188100/90188001/6c32c87d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90190000/90188100/90188001/a4e74534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pittsburgh Pennsylvania house

[](https://www.expedia.ca/Pittsburgh-Hotels-Pittsburgh-Pennsylvania-House.h90188001.Hotel-Information)

South Side Flats

6.0/10

(2)

"Great 3 bed, 1 bathroom place to stay in Southside Pittsburgh. One block walk to E Carson St. Be sure to bring your own bath towels and soap."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Adrian C.

CA $170

CA $389 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Pittsburgh-Hotels-Pittsburgh-Pennsylvania-House.h90188001.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/120000000/119730000/119727100/119727041/e331b873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119730000/119727100/119727041/a72f8237.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119730000/119727100/119727041/02386db5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119730000/119727100/119727041/e2054544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Light Room

[](https://www.expedia.ca/The-Light-Room.h119727041.Hotel-Information)

McKeesport

9.6/10

Exceptional

(4)

"The house has a very peaceful atmosphere."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Susan G.

CA $124

CA $234 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/The-Light-Room.h119727041.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/114000000/113900000/113897200/113897106/990b7d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/114000000/113900000/113897200/113897106/b993392f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/114000000/113900000/113897200/113897106/d8440418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113900000/113897200/113897106/edeac1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Upper Room

[](https://www.expedia.ca/Pittsburgh-Hotels-The-Upper-Room.h113897106.Hotel-Information)

McKeesport

9.4/10

Exceptional

(6)

"Great place and an awesome host!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John B.

CA $131

CA $241 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Pittsburgh-Hotels-The-Upper-Room.h113897106.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/124000000/123440000/123431700/123431662/9072e668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/124000000/123440000/123431700/123431662/d653c9d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/124000000/123440000/123431700/123431662/092d1c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123440000/123431700/123431662/38ec1a9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 4-bedroom house in beautiful Pittsburgh

[](https://www.expedia.ca/Pittsburgh-Hotels-Spacious-4-Bedroom-House-In-Beautiful-Pittsburgh.h123431662.Hotel-Information)

Pittsburgh

CA $110

CA $463 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Pittsburgh-Hotels-Spacious-4-Bedroom-House-In-Beautiful-Pittsburgh.h123431662.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/90000000/89991800/89991722/fd868765.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/90000000/89991800/89991722/6ca32243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/90000000/89991800/89991722/2dbc4d8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/90000000/89991800/89991722/fec3a20a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ★ HostWise Stays ★ 4 Blocks From UPMC Children's

[](https://www.expedia.ca/Pittsburgh-Hotels-Colorful-Home-In-A-Great-Location.h89991722.Hotel-Information)

Lawrenceville

10/10

Exceptional

(14)

"Great location and communication from host! The home was clean, comfortable, and exactly as described. We loved and appreciated the kitchen amenities! We very much enjoyed our stay. We would absolutely stay here again and highly recommend this rental. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Heather S.

CA $107

CA $275 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Pittsburgh-Hotels-Colorful-Home-In-A-Great-Location.h89991722.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/66000000/65310000/65300800/65300778/6f1b4e7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/66000000/65310000/65300800/65300778/f95fb7b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/66000000/65310000/65300800/65300778/4a7a11bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/66000000/65310000/65300800/65300778/7ecf2196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Craftsman Charmer | Easy Access to City & Airport

[](https://www.expedia.ca/Pittsburgh-Hotels-Craftsmen-Charmer-With-Easy-City-Airport-Access.h65300778.Hotel-Information)

Crafton Heights

9.6/10

Exceptional

(16)

"We enjoyed our visit to Pittsburgh, we would definitely stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jamie B.

CA $95

CA $248 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Pittsburgh-Hotels-Craftsmen-Charmer-With-Easy-City-Airport-Access.h65300778.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73670000/73660600/73660580/7d0f2ac6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/74000000/73670000/73660600/73660580/5c7fe0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73670000/73660600/73660580/4c7038a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73670000/73660600/73660580/af415194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Restful Nest near downtown

[](https://www.expedia.ca/Pittsburgh-Hotels-Restful-Nest-Near-Downtown.h73660580.Hotel-Information)

Brookline

9.0/10

Wonderful

(7)

"This house was perfect for our weekend stay for the Steelers game. It is just a few miles drive to the stadium. There is a large variety of restaurants close by. The house was clean and comfortable and well stocked with whatever you may need for your stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mark D.

CA $155

CA $409 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Pittsburgh-Hotels-Restful-Nest-Near-Downtown.h73660580.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107760000/107757000/107756973/w1199h800x1y1-729c05fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107760000/107757000/107756973/w1199h800x1y1-007f17cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/108000000/107760000/107757000/107756973/w1200h800x0y1-f7bcb03a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/108000000/107760000/107757000/107756973/227a7253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish House near Frick Park

[](https://www.expedia.ca/Pittsburgh-Hotels-Stylish-House-Near-Frick-Park.h107756973.Hotel-Information)

Squirrel Hill South

9.8/10

Exceptional

(9)

"Stayed for the US Open. Check in was easy and property was clean and comfortable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joshua H.

CA $156

CA $326 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Pittsburgh-Hotels-Stylish-House-Near-Frick-Park.h107756973.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-26&endDate=2025-12-27&regionId=6343590&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Condos

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Private vacation homes

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Pennsylvania%2C+United+States+of+America&regionId=6343590&latLong=40.425303%2C-79.977027&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=South+Side%2C+Pennsylvania%2C+United+States+of+America&regionId=6343590&latLong=40.425303%2C-79.977027&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-15&d2=2026-03-15&lodging=CABIN)

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## Top South Side Hotel Reviews

![Wyndham Grand Pittsburgh Downtown](https://images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg)

### Wyndham Grand Pittsburgh Downtown

10/10 Excellent

"Didn’t eat breakfast. The staff was friendly and wonderful overall. "

[](https://expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.Hotel-Information)

![Hyatt Regency Pittsburgh International Airport](https://images.trvl-media.com/lodging/1000000/470000/464100/464013/1caa2404_y.jpg)

### Hyatt Regency Pittsburgh International Airport

10/10 Excellent

"Nice place Nice professional staff"

[](https://expedia.ca/Pittsburgh-Hotels-Hyatt-Regency-Pittsburgh-International-Airport.h464013.Hotel-Information)

![Omni William Penn Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg)

### Omni William Penn Hotel

10/10 Excellent

"Wonderful staff and accommodations..great location especially if you plan on attending something at PPG arena"

[](https://expedia.ca/Pittsburgh-Hotels-Omni-William-Penn-Hotel.h2998.Hotel-Information)

![The Landing Hotel at Rivers Casino ](https://images.trvl-media.com/lodging/104000000/103310000/103300300/103300276/e4bbb9fc_y.jpg)

### The Landing Hotel at Rivers Casino 

10/10 Excellent

"Breakfast was a highlight and management, especially Connie and Dravin made the trip pleasant."

[](https://expedia.ca/Pittsburgh-Hotels-The-Landing-Hotel-At-Rivers-Casino.h103300276.Hotel-Information)

![Kimpton Hotel Monaco Pittsburgh by IHG](https://images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/2ee575df_y.jpg)

### Kimpton Hotel Monaco Pittsburgh by IHG

10/10 Excellent

"Room was immaculately cleaned. Staff was friendly and helpful. "

[](https://expedia.ca/Pittsburgh-Hotels-Kimpton-Hotel-Monaco-Pittsburgh.h8645076.Hotel-Information)

![Drury Plaza Hotel Pittsburgh Downtown](https://images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/9183e33f_y.jpg)

### Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent

"Every detail was amazing "

[](https://expedia.ca/Pittsburgh-Hotels-Drury-Plaza-Hotel-Pittsburgh-Downtown.h15178439.Hotel-Information)

![Courtyard by Marriott Pittsburgh University Center](https://images.trvl-media.com/lodging/1000000/10000/3300/3215/d1089d4e_y.jpg)

### Courtyard by Marriott Pittsburgh University Center

10/10 Excellent

"Friendly staff, beautiful clean rooms "

[](https://expedia.ca/Pittsburgh-Hotels-Wyndham-Pittsburgh-University-Center.h3215.Hotel-Information)

![Joinery Hotel Pittsburgh, Curio Collection by Hilton](https://images.trvl-media.com/lodging/18000000/17910000/17900800/17900777/6b099d23_y.jpg)

### Joinery Hotel Pittsburgh, Curio Collection by Hilton

10/10 Excellent

"Great staff! Room was nice. The bars nice. Very Walkable to area restaurants & Market Square. Valet service was fast. "

[](https://expedia.ca/Pittsburgh-Hotels-Distrikt-Hotel-Pittsburgh.h17900777.Hotel-Information)

![Hilton Garden Inn Pittsburgh Downtown](https://images.trvl-media.com/lodging/10000000/9380000/9378100/9378026/c02cf3a6_y.jpg)

### Hilton Garden Inn Pittsburgh Downtown

10/10 Excellent

"Clean roon, greay front desk staff. The only issue was the thermostat taking FOREVER to heat up and never got over 69 degrees. "

[](https://expedia.ca/Pittsburgh-Hotels-Hilton-Garden-Inn-Pittsburgh-Downtown.h9378026.Hotel-Information)

## Find out more about South Side

## South Side Vacation Homes information

| Number of reviews | 234                |
| ----------------- | ------------------ |
| Accommodation     | 626 Vacation Homes |
| Lowest Price      | CA $234            |
| Highest Price     | CA $926            |

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- [Flights to Pittsburgh ](https://www.expedia.ca/Cheap-Flights-To-Pittsburgh.d601717.Travel-Guide-Flights)

- [Ppg Paints Arena ](https://www.expedia.ca/PPG-Paints-Arena-Downtown-Pittsburgh.d6140367.Vacation-Attraction)
- [Visit Bluff ](https://www.expedia.ca/Pittsburgh-Bluff.dx553248634333003951)
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