Title: Beach Vacations in South Side 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6343589/4aa9fc8d-6a54-47bc-ab37-20ca38b4643c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Beach Vacations ## Book a Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place ## Flight and Beach hotel deals in South Side Price found within the past 48 hours. Click for updated prices. ![Omni William Penn Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2998/c923b3f2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni William Penn Hotel Downtown Pittsburgh CA $943 per person Nov 21 - Nov 23 found 1 day ago Roundtrip non-stop flight included Québec (YQB) to Pittsburgh (PIT) 9/10 Wonderful! (1,724 reviews) Beautiful hotel - Clean and comfortable room Reviewed on Oct 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YQB&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2998&paandie=true&HotelClass=40&dealMarker=NdFnuoRmI-uCae-shPb_qKO1JT5Nb5XJ2fOc9qcH2DDmXCDHKBRhFbUyZD-NAiSl) ![Fairmont Pittsburgh](https://images.trvl-media.com/lodging/4000000/3060000/3056400/3056317/801aa0d0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Pittsburgh Downtown Pittsburgh CA $1,292 per person Dec 27 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YYZ) to Pittsburgh (PIT) 8.8/10 Excellent! (1,008 reviews) Came for our anniversary and The Capital Grille was only a one minute walk from the hotel! Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-02/?FromAirport=YYZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=3056317&paandie=true&HotelClass=40&dealMarker=xd6BJpUbwWMObx8qG3PDGX4ypSccgJcAgdKOlOWxX9fg58pmQAIbgxDNNaZjHsMs) ![Placemakr Downtown Pittsburgh at The Pennsylvanian](https://images.trvl-media.com/lodging/115000000/114320000/114312800/114312743/c173f17f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Placemakr Downtown Pittsburgh at The Pennsylvanian Downtown Pittsburgh CA $1,267 per person Dec 27 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YYZ) to Pittsburgh (PIT) 7.8/10 Good! (26 reviews) Thank you Josh for helping us with our second reservation. The hotel is elegant with old school charm. The suites has washer/ dryers and full kitchen and very friendly to us bicyclists Reviewed on Sep 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-02/?FromAirport=YYZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=114312743&paandie=true&HotelClass=40&dealMarker=xd6BJpUbwWMObx8qG3PDGX4ypSccgJcAgdKOlOWxX9dj_Jll7UQzcdSjCoiVP5nB) ![Kimpton Hotel Monaco Pittsburgh by IHG](https://images.trvl-media.com/lodging/9000000/8650000/8645100/8645076/2ee575df_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Hotel Monaco Pittsburgh by IHG Downtown Pittsburgh CA $1,394 per person Dec 27 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YYZ) to Pittsburgh (PIT) 9.4/10 Exceptional! (1,243 reviews) It was nice and clean, the bed was comfortable. The staff was nice and attentive. 5/5 Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-02/?FromAirport=YYZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8645076&paandie=true&HotelClass=40&dealMarker=xd6BJpUbwWMObx8qG3PDGX4ypSccgJcAgdKOlOWxX9d8doTUpPyNkE_r-S5tIIxt) ![Kasa South Side Pittsburgh](https://images.trvl-media.com/lodging/71000000/70900000/70891100/70891071/6ac37499_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kasa South Side Pittsburgh South Side Flats CA $1,605 per person Dec 27 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YYZ) to Pittsburgh (PIT) 8.2/10 Very Good! (100 reviews) Great location, not best parking situation - was a bit confusing given you could "reserve a spot" for parking but then directions with check-in mentioned no parking was available for free. Very beautiful view and nice apartment but was not the cleanest. Would stay again as was perfect for a work trip. Great communication! Reviewed on Sep 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2026-01-02/?FromAirport=YYZ&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&hotelId=70891071&paandie=true&HotelClass=40&dealMarker=X8bqsHnU4UDAtHcXSdsp5Up2UVz3MnlYlAkXoTJbyPIV-BnddFjhL0sRzMf3bXK2) Don't see what you're looking for? See all available trips from Columbus to South Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-28/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=PIT&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find the best beach vacations in South Side #### What are some benefits when booking beach vacations in South Side? When you travel to the beach in South Side, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip. #### How can I book the best beach vacations in South Side? To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your South Side trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit. #### Can I book cheap beach vacations in South Side? There are quite a few things you can do to get cheap beach vacations in South Side. Prices range from CA $943, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out. #### Can I book beach packages? Yes, and you'll find quite a few beach packages available in South Side. These package deals let you save by booking your accommodation and your flight together with savings of up to 13. #### Why should I book family beach vacations? When you're travelling with the family to South Side, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room. #### How can I find a beachfront vacation in South Side? It's easy to find a beachfront vacation accommodation in South Side using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline. #### How can I book last-minute beach vacations? Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and South Side as your destination and see what's available. #### Can I find all-inclusive beach vacations ? Yes, all you have to do to find all-inclusive beach vacations in South Side is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance. #### Can I book a beach trip that's fully refundable? Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Pittsburgh. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too. #### Why should I book beach vacations with Expedia? When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips. ## Beach Hotels in South Side ![Southside Flats Cozy Quiet Luxury](https://images.trvl-media.com/lodging/66000000/66000000/65995200/65995165/w447h300x1y0-885c8613_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Southside Flats Cozy Quiet Luxury Pittsburgh - 6 min walk from Rex Theater Stay at this apartment in Pittsburgh. Enjoy free breakfast, cable/satellite TV service, and an in-room coffeemaker. Popular attractions PPG Paints Arena and ... Little Gem "I seen this place being almost last minute booking for a 2024 Iron Maiden tour. It was close to alot of bars and good food.Very nice to park and just walk eventful learning experience ofPittsburgh . The locals are down to earth and seems safe place. Of i come back i will.look this place up again ..." Reviewed on Nov 9, 2024 [](https://expedia.ca/Pittsburgh-Hotels-Southside-Flats-Cozy-Quiet-Luxury.h65995165.Hotel-Information) ![Gorgeous Southside Slopes home with outdoor hot tub and city view!](https://images.trvl-media.com/lodging/33000000/32570000/32565000/32564945/270-1a3f9a6e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Gorgeous Southside Slopes home with outdoor hot tub and city view! Pittsburgh - 19 min walk from Rex Theater Book a stay at this family-friendly vacation home in Pittsburgh. Enjoy a water park, a garden, and laundry facilities. Popular attractions PPG Paints Arena and ... 9.8/10 Exceptional! (55 reviews) "Awesome view of the city!" Reviewed on Sep 22, 2025 [](https://expedia.ca/Pittsburgh-Hotels-Gorgeous-Southside-Slopes-Home-With-Outdoor-Hot-Tub-And-City-View.h32564945.Hotel-Information) ![Pittsburgh’s Tropicana with outdoor year round hot tub. Fantastic location! ](https://images.trvl-media.com/lodging/32000000/31570000/31566300/31566226/d4576528_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pittsburgh’s Tropicana with outdoor year round hot tub. Fantastic location! Pittsburgh - 14 min walk from Rex Theater Book a stay at this family-friendly vacation home in Pittsburgh. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions PPG Paints Arena ... 9.8/10 Exceptional! (48 reviews) Pittsburgh Rocks! "We had a Wonderful time and the house was fantastic. Lots of amenities for the kids to play in the game room. We really enjoyed the outside patio area where we spent most of our evening. Everything we visited was within minutes of the location. We would definitely stay here again." Reviewed on Aug 11, 2025 [](https://expedia.ca/Pittsburgh-Hotels-Pittsburghs-Tropicana-With-Outdoor-Year-Round-Hot-Tub-Fantastic-Location.h31566226.Hotel-Information) [See all 1,821 properties in South Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6343590) 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. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Beach Vacation Destinations > - [Virginia beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/10271/Virginia-Beach) > - [Myrtle beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/601685/Myrtle-Beach) > - [Miami beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8833/Miami-Beach) > - [Florida beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/211/Florida) > - [Barbados beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/16/Barbados) > - [South beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6138745/South-Beach) > - [Palm beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/9061/Palm-Beach) > - [Daytona beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023995/Daytona-Beach) > - [Newport beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8111/Newport-Beach) > - [Vero beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023660/Vero-Beach) > - [India beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/80/India) > - [Laguna beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6298668/Laguna-Beach) > - [Ontario beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/2680/Ontario) > - [Canada beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/31/Canada) > - [Barcelona beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/179992/Barcelona) > - [Fort Myers beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/7194/Fort-Myers-Beach) > - [Portugal beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/147/Portugal) > - [Italy beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/86/Italy) > - [Thailand beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/178/Thailand) > - [France beach vacations](https://www.expedia.ca/lp/theme-vacations/beach-vacations/59/France) ## More Vacations Ideas [Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d6343590.Travel-Guide-Flights)[South Side Hotels](https://expedia.ca/South-Side-Hotels.d6343590.Travel-Guide-Hotels)[South Side Vacation Rentals](https://expedia.ca/South-Side-Vacation-Rentals.d6343590.Travel-Guide-VacationRentals)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d6343590.Car-Rental-Guide)[South Side Vacations](https://expedia.ca/South-Side.d6343590.Destination-Travel-Guides)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d6343590.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)