South Side holiday homes

We found 1,328 holiday rentals — enter your dates for availability

Discover a selection of 59 homes, 40 apartments and other holiday rentals in South Side that are perfect for your trip. Whether you're going on holiday with family or friends, Vrbo holiday homes have the best amenities for spending time at your holiday home, including Wi-Fi and parking. You're sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - South Side

Showing deals for:12 Sept - 19 Sept

Image gallery for FIVE STARS! For SPORTS, THEATER, STADIUMS, CASINO, RESERVED PARKING, A/C COMFORT

The Pittsburgh Loft House is Warmth, Comfort, Convenience, Lifetime Memories!
9.8 out of 10 rating
Exceptional
(55 reviews)

FIVE STARS! For SPORTS, THEATER, STADIUMS, CASINO, RESERVED PARKING, A/C COMFORT

Pittsburgh, PA

12% off
Price is NZ$4,614
NZ$659 per night
includes taxes & fees
FIVE STARS! For SPORTS, THEATER, STADIUMS, CASINO, RESERVED PARKING, A/C COMFORT

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Travel to theatrical South Side

Enjoy the area's theatre scene, live music and architecture with a rental holiday home in South Side. This city is welcoming and cosmopolitan, recognised for its bars, restaurants and sporting events. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around South Side

Do you want to find attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes South Side a fun spot to go on holiday. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • National Aviary (2.6 mi / 4.2 km)
  • Sandcastle Water Park (3.2 mi / 5.1 km)
  • Frick Park (3.8 mi / 6.2 km)
  • Kennywood (6.5 mi / 10.5 km)
  • Oakmont Country Club (10.5 mi / 16.9 km)
  • South Park Golf Course (7 mi / 11.3 km)

Exploring the natural features in South Side

Whether you're looking for adventure or just want to appreciate the scenery, South Side is a great place to get outside. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • PNC Park (2.1 mi / 3.4 km)
  • Phipps Conservatory (1.8 mi / 2.9 km)
  • Schenley Park (1.9 mi / 3.1 km)
  • Point State Park (2 mi / 3.3 km)
  • Frick Park (3.8 mi / 6.2 km)
  • Pittsburgh Botanic Garden (10.2 mi / 16.3 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in South Side?
The most sought-after types of holiday homes in South Side are houses. Prefer something different? Bookabach offers a variety of options to match our guests’ unique needs, so you’ll see holiday homes in loads of sizes and shapes. The ideal fit is waiting for you — book yours today.
How much does it cost to rent a holiday home in South Side?
The average price for a holiday home in South Side depends on several factors, like property type, season and length of stay. Whether you’re searching for a sprawling villa with room to move around or a cosy cabin just for the two of you, just add your travel dates to see stays with great value.
How much does it cost to rent a beach house in South Side?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside holiday home. Type in your South Side travel dates to see all your options on Bookabach. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to select the features and amenities you want in your home.
Are there pet-friendly holiday homes in South Side?
Pack a squeezy toy and a bone for the pup in your life because South Side has 72 holiday homes that welcome pets with open arms. Let your four-legged pal have fun with the family at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates then check our “Pets allowed” filter box.
What are popular home amenities in South Side?
When it comes to home amenities that guests prefer in South Side, mountain views, a garden and a nearby river rank highest. With Bookabach holiday homes, there are choices to fit your taste and style, whether you’re going on a holiday with friends, relatives or even pets.
Are there large group holiday homes in South Side?
With 16 holiday homes that can host 10 guests or more in South Side, you don’t have to cross anyone off the invite list. From family get-togethers to events like Thanksgiving or Christmas parties, Bookabach will help you find a large group home to match the occasion.
Are there holiday homes in South Side that welcome kids?
With 72 family-friendly holiday homes available in South Side, there’s never been a better time to introduce your little ones to the pleasures of travel. Simply check our “Properties good for families” filter box to search for stays that feature conveniences ideal for holidaying families, such as kitchens, outdoor spaces, entertainment units and bunk beds.
What are the top attractions for families in South Side?
Keeping the kiddos entertained during your holiday in South Side is a cinch with these family-friendly attractions:

  • Pittsburgh Zoo and PPG Aquarium
  • Carnegie Science Centre
  • Carnegie Museum of Natural History

Are there one-bedroom holiday homes in South Side?
There are 10 one-bedroom properties in South Side to select from. A one-bedroom holiday home is a great choice if it’s just the two of you or if you’re travelling alone. Add in more space, convenience and privacy compared to a standard hotel, and you’ve got yourself an unforgettable break.
Can I find two-bedroom holiday homes in South Side?
Take off with your besties and enjoy a relaxing escape in one of the 19 two-bedroom holiday homes South Side has to offer.
Are there holiday homes with WiFi in South Side?
You’ll have a choice of 25 holiday homes with WiFi in South Side. If you want to disconnect from daily life during your trip, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in South Side?
Pick your dates and then make use of the filters to search for holiday homes with air conditioning in South Side on Bookabach. With 64 air-conditioned properties on offer here, you can look forward to a cool and comfortable trip.
How old do you have to be to rent a holiday home in South Side?
The minimum required age is normally 16, 18 or 21. It can differ between properties on Bookabach, so check the rules of your chosen South Side stay before making a booking.
How long can I rent a holiday home in South Side for?
It really depends on the South Side property. To view a list of options offering extended stays, simply enter your travel dates and number of guests into Bookabach’s search page. Enjoy having the entire property to yourself, along with comforts such as a full kitchen, air conditioning and a backyard where the kids can run around and play. Keep your eyes open for long-term stays that offer weekly or monthly discounts.

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