Title: South Side Vacation Home Rentals : 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/473000/473595-South-Side-Pittsburgh.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # South Side Vacation Rentals - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6343590&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select South Side Vacation Homes ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106560000/106550400/106550398/cc867c72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/107000000/106560000/106550400/106550398/93888023.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) ### Central 5BD Getaway - Spacious Home w/ BBQ 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) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112980000/112970900/112970868/4f5d5fc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, travel crib, free WiFi](https://images.trvl-media.com/lodging/113000000/112980000/112970900/112970868/72384897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112980000/112970900/112970868/0cc6e416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/113000000/112980000/112970900/112970868/73ee684a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### South Side Vibe! Pittsburgh's best location South Side Flats 9.4/10 Exceptional (8) "Property as described, Bed was very comfortable. Nick was very responsive. It's hard to find a place that will allow dogs over 100 pounds so we were happy to find this spot. It has a fenced backyard and a deck on the second level so our pup had spots to enjoy being outside. Our dog figured out how to open the front door by pushing down on the door lever and he escaped. However a mailman and a neighbor grabbed him. So you will have good neighbors here. Parking in the evenings was a challenge as... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa B. CA $101 CA $305 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Pittsburgh-Hotels-South-Side-Vibe-Pittsburghs-Best-Location.h112970868.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/a7475201.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) ### Hot Tub | King Bed | Games | Free Parking South Side Flats 10/10 Exceptional (3) "Very clean! Amenities were fantastic Really loved the backyard with the hot tub. Quiet area and loved being able to walk to the local bars/restaurants. Brandon was always a text away. Parking was also easy. Would definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ruth F. CA $196 CA $529 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Pittsburgh-Hotels-Hot-Tub-King-Bed-Free-Parking-Arcade.h113630660.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99780000/99777000/99776944/94fc5be6.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) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99780000/99777000/99776944/25467d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### City Skyline - Outside decks - Contemporary 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 $181 CA $581 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Pittsburgh-Hotels-City-Skyline-Outside-Decks-Contemporary.h99776944.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) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/97000000/96970000/96961700/96961617/cfd36995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Bed | Free Parking | Arcade | Fire Pit South Side Flats 10/10 Exceptional (21) "We stayed there for my sons wedding. It made our wonderful wedding week even more fun." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine P. CA $182 CA $511 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Pittsburgh-Hotels-King-Bed-Free-Parking-Arcade.h96961617.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 South Side Flats 8.0/10 Very good (2) "Faran was an excellant host. Very responsive to all questions and issues. Property was very well maintained. Limited kitchen utensils/bakeware for cooking and/or storing food. Plenty of space for our family of 8. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna M. CA $123 CA $460 total includes taxes & fees Nov 18 - Nov 19 [](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/84000000/83570000/83566200/83566134/391c97af.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) ![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) ### Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside! South Side Flats 7.8/10 Good (8) "Tom was very communicative during the whole stay and had great recommendations! We loved the place, well situated on the South side for easy walking along Carson. Wonderful time in Pittsburgh! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan H. CA $70 CA $346 total includes taxes & fees Nov 18 - Nov 19 [](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/74000000/73040000/73032000/73031981/058c641f.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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73040000/73032000/73031981/9cb6c2d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ❤️Cozy Townhome on Carey with Private Deck Space ❤️ South Side Flats 8.2/10 Very good (32) "We had a good stay. Thanks! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vanina CA $70 CA $349 total includes taxes & fees Nov 24 - Nov 25 [](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) ![Interior](https://images.trvl-media.com/lodging/91000000/90020000/90011500/90011428/37b9f9dc.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) ![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) ### Beautiful Hillside Home with Incredible City Views!! Great Location and Privacy! South Side Slopes 10/10 Exceptional (14) "Great house with amazing views of the city. The property manager is super easy to get ahold of and talk to. We really enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah W. CA $449 CA $942 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Pittsburgh-Hotels-Incredible-Views-Perfect-Combination-Of-Luxury-And-Entertainment.h90011428.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114880000/114877800/114877763/c67a9a5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/115000000/114880000/114877800/114877763/76b6c5b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114880000/114877800/114877763/b9406e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114880000/114877800/114877763/7fc9769e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside South Side Flats 7.0/10 Good (4) "Excellent communication with owner. Fast, friendly and courteous. Located about 450 meter walk up a large hill from Penn Avenue (bus 88) which is about 35 minutes to downtown. Apartment showing its age but fair value for cost. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jarrod CA $70 CA $332 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Pittsburgh-Hotels-Charming-1-Bedroom-House-With-AC.h114877763.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) ![Exterior detail](https://images.trvl-media.com/lodging/97000000/96760000/96758700/96758626/bd3cd0a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96760000/96758700/96758626/5c9fe64a.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) ### Big Dog Coffee's Little Red Cat/Historic Pittsburgh Home/FREE Parking Spaces South Side Flats 10/10 Exceptional (20) "Beautiful property with all the amenities you could ever need for a weekend getaway " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda G. CA $471 CA $870 total includes taxes & fees Dec 2 - Dec 3 [](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) ![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) ![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) ### King Bed | Free Parking | BBQ | Fire pit | Arcade South Side Flats 9.8/10 Exceptional (66) "Property was great. Parking not difficult. Great location lots of food options. Very comfortable. Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marianne G. CA $171 CA $513 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Pittsburgh-Hotels-Posh-4-Bedroom-On-Carson-St-W-Pro-Cleaning.h87368723.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) ![TV](https://images.trvl-media.com/lodging/120000000/119730000/119727100/119727041/02386db5.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) ![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 McKeesport 9.6/10 Exceptional (4) "Communication with host was excellent. The property looks like it's in the middle of some work, which left some unfinished appearances (outlet covers, spackling/paint, things like that). It was left very clean by the clean up crew.Biggest drawback was the temperature. Bedrooms are small which led to the bed being right against a window, and with the air conditioner still installed, the cold air came seeping through the cracks all night long. Also, when we woke up and checked the thermostat,... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric J. CA $112 CA $222 total includes taxes & fees Nov 29 - Nov 30 [](https://www.expedia.ca/The-Light-Room.h119727041.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107860000/107853200/107853177/214a6dbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107860000/107853200/107853177/cd834cd9.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/108000000/107860000/107853200/107853177/99ac3427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107860000/107853200/107853177/8c11cb44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ★ HostWise Stays ★ Casa Santorini - Aegean Inspired, Instaworthy! Lawrenceville 10/10 Exceptional (2) "We had a wonderful stay during our visit to Pittsburgh. Our host Chad was very helpful and responsive when we had questions. It was our first time in Lawrenceville and it exceeded our expectations! Love the neighborhood and its vibe! Looking forward to our next trip! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terri W. CA $146 CA $471 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Pittsburgh-Hotels-Casa-Santorini-Aegean-Inspired.h107853177.Hotel-Information) ![House, 4 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/117000000/116470000/116467600/116467537/50ca0ef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/117000000/116470000/116467600/116467537/6b760493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms](https://images.trvl-media.com/lodging/117000000/116470000/116467600/116467537/5a41f442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 4 Bedrooms | Exterior](https://images.trvl-media.com/lodging/117000000/116470000/116467600/116467537/2c45777a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-friendly 4br Near Kennywood & Pittsburgh 4 Bedroom Home West Mifflin CA $192 CA $494 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Pittsburgh-Hotels-Pet-Friendly-4br-Near-Kennywood-Pittsburgh-4-Bedroom-Home.h116467537.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/92000000/91170000/91161500/91161412/0fa41e4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91170000/91161500/91161412/9607f678.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91170000/91161500/91161412/326f21c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/92000000/91170000/91161500/91161412/977aa2c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 183 Banner Way - Lawrenceville Lawrenceville 10/10 Exceptional (10) "Very nice place. Close to Butler street which has great restaurants & shops!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather z. CA $122 CA $311 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Pittsburgh-Hotels-HostWise-Stays-Private-Hot-Tub-King-Bed-Workspace-Kids-Welcome.h91161412.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) ![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) ![Interior](https://images.trvl-media.com/lodging/90000000/90000000/89991800/89991722/6ca32243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/90000000/89991800/89991722/69294c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ★ HostWise Stays ★ 4 Blocks From UPMC Children's Lawrenceville 10/10 Exceptional (14) "After years of visiting my son in Pittsburgh and staying at hotels I decided to try a neighborhood stay. The place was lovely - exactly as pictured, with great amenities (including fresh coffee beans and a coffee grinder!). I can't wait to keep exploring the city with other HostWise properties. Everything from booking to check out was seamless. Thanks Chad! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica M. CA $94 CA $264 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Pittsburgh-Hotels-Colorful-Home-In-A-Great-Location.h89991722.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/25000000/24040000/24039600/24039579/cbc59fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/25000000/24040000/24039600/24039579/6b6791f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, Netflix, streaming services, offices](https://images.trvl-media.com/lodging/25000000/24040000/24039600/24039579/e86c6544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/25000000/24040000/24039600/24039579/25698b72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 3BR Home with Cozy Front & Back Porches! Munhall 9.4/10 Exceptional (28) "Jenna is very good host and very responsive. Thanks for the great experience." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David K. CA $160 CA $332 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Pittsburgh-Hotels-Beautiful-3BR-Home-With-Cozy-Front-Back-Porches.h24039579.Hotel-Information) ![TV, foosball, books](https://images.trvl-media.com/lodging/109000000/108730000/108720200/108720144/w1199h800x1y1-19ffcb8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, foosball, books](https://images.trvl-media.com/lodging/109000000/108730000/108720200/108720144/w1200h800x0y1-bf7ad2b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108730000/108720200/108720144/w1199h800x1y1-afedafd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108730000/108720200/108720144/w1200h800x0y1-5a068f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern and Spacious House North Side 9.4/10 Exceptional (3) "The house was cleaned and had lots of space. One bath for the bedrooms, a powder room on the main floor and a shower in the basement with toilet. My grandchild came to visit and enjoyed the swings and bunnies in the yard" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann T. CA $125 CA $428 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Pittsburgh-Hotels-Modern-And-Spacious-House.h108720144.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87580000/87578500/87578460/86c6c694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/88000000/87580000/87578500/87578460/983bbd40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/88000000/87580000/87578500/87578460/e5145a27.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/88000000/87580000/87578500/87578460/98e9929a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fire Pit + Family Friendly + Great Location! Bloomfield 9.8/10 Exceptional (6) "I booked this home to visit our two first-year students at Carnegie Mellon University last October. The house was very nice, clean, and well-kept. The highlight of the house is the beautiful piano in the living room. We are a musical family, so we played it all the time. The neighborhood is quiet, and the host was very responsive and provided every amenity we could ask for. I'm sad I waited too late to book the property for the CMU carnival in April. It was the first property I looked up, but as... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric P. CA $115 CA $360 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Pittsburgh-Hotels-Fire-Pit-Family-Friendly-Great-Location.h87578460.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=2025-11-26&endDate=2025-11-27®ionId=6343590&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Private-Vacation-Homes.d6343590-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Private-Vacation-Homes.d6343590-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top South Side Hotel Reviews ![DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown](//images.trvl-media.com/lodging/1000000/10000/6200/6149/4d6098b6_y.jpg) ### DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown 10/10 Excellent "Clean room great staff very helpful " [](https://expedia.ca/Pittsburgh-Hotels-DoubleTree-By-Hilton-Hotel-Suites-Pittsburgh-Downtown.h6149.Hotel-Information) ![Hyatt Regency Pittsburgh International Airport](//images.trvl-media.com/lodging/1000000/470000/464100/464013/1caa2404_y.jpg) ### Hyatt Regency Pittsburgh International Airport 10/10 Excellent "Comfortable bdds" [](https://expedia.ca/Pittsburgh-Hotels-Hyatt-Regency-Pittsburgh-International-Airport.h464013.Hotel-Information) ![Kimpton Hotel Monaco Pittsburgh by IHG](//images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/2ee575df_y.jpg) ### Kimpton Hotel Monaco Pittsburgh by IHG 10/10 Excellent "The staff was very friendly. The amenities for our pets were above any expectation." [](https://expedia.ca/Pittsburgh-Hotels-Kimpton-Hotel-Monaco-Pittsburgh.h8645076.Hotel-Information) ![The Landing Hotel at Rivers Casino ](//images.trvl-media.com/lodging/104000000/103310000/103300300/103300276/e4bbb9fc_y.jpg) ### The Landing Hotel at Rivers Casino 10/10 Excellent "Great room: large, with a comfy bed, lovely river view. " [](https://expedia.ca/Pittsburgh-Hotels-The-Landing-Hotel-At-Rivers-Casino.h103300276.Hotel-Information) ![Homewood Suites by Hilton Pittsburgh Downtown](//images.trvl-media.com/lodging/13000000/12440000/12435100/12435017/48a1d3a1_y.jpg) ### Homewood Suites by Hilton Pittsburgh Downtown 10/10 Excellent "Clean, homey, cozy, staff was super accommodating " [](https://expedia.ca/Pittsburgh-Hotels-Homewood-Suites-By-Hilton-Pittsburgh-Downtown.h12435017.Hotel-Information) ![Drury Plaza Hotel Pittsburgh Downtown](//images.trvl-media.com/lodging/16000000/15180000/15178500/15178439/9183e33f_y.jpg) ### Drury Plaza Hotel Pittsburgh Downtown 10/10 Excellent "Comfortable rooms, great location within walking distance of many tourist attractions, friendly and helpful staff, good free breakfast and evening happy hour snacks. Would definitely stay again at this location. Great stay overall and would highly recommend! " [](https://expedia.ca/Pittsburgh-Hotels-Drury-Plaza-Hotel-Pittsburgh-Downtown.h15178439.Hotel-Information) ![Wyndham Grand Pittsburgh Downtown](//images.trvl-media.com/lodging/1000000/30000/25600/25509/14f19a0a_y.jpg) ### Wyndham Grand Pittsburgh Downtown 10/10 Excellent "Clean spacious room. " [](https://expedia.ca/Pittsburgh-Hotels-Wyndham-Grand-Pittsburgh-Downtown.h25509.Hotel-Information) ![Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG](//images.trvl-media.com/lodging/1000000/920000/914500/914423/76c1ea4b_y.jpg) ### Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG 10/10 Excellent "Great breakfast choices and clean room" [](https://expedia.ca/Pittsburgh-Hotels-Holiday-Inn-Express-Hotel-Suites-Pittsburgh-South-Side.h914423.Hotel-Information) ![Courtyard by Marriott Pittsburgh University Center](//images.trvl-media.com/lodging/1000000/10000/3300/3215/d1089d4e_y.jpg) ### Courtyard by Marriott Pittsburgh University Center 10/10 Excellent "Had a great stay!" [](https://expedia.ca/Pittsburgh-Hotels-Wyndham-Pittsburgh-University-Center.h3215.Hotel-Information) ## Find out more about South Side ## South Side Vacation Homes information | Number of reviews | | | --- | --- | | Accommodation | Vacation Homes | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Other - More ways to book - [5 Star Hotels in Arlington](https://www.expedia.ca/5Star-Arlington-Pittsburgh-Hotels.s50-n804081383557210112-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Knoxville](https://www.expedia.ca/5Star-Knoxville-Pittsburgh-Hotels.s50-n804083795867832320-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in St. Clair](https://www.expedia.ca/5Star-St-Clair-Pittsburgh-Hotels.s50-n804081561040011264-0.Travel-Guide-Filter-Hotels) - [Hotels near Acrisure Stadium](https://www.expedia.ca/Acrisure-Stadium-Hotels.0-l6058087-0.Travel-Guide-Filter-Hotels) - [B&B in Allegheny County](https://www.expedia.ca/Allegheny-County-Bed-And-Breakfast.d553248635083907360-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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