South Side holiday homes

We found 1,460 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – South Side

Showing deals for:18 Dec - 25 Dec

Room
Interior
Interior
Private kitchen
Exceptional
(8 reviews)

NFL Draft Stay-Private Home Minutes from Acrisure Stadium-Sleeps 8- Park Free

Pittsburgh

7% off
NZ$3,736
for 7 nights, 1 home
NZ$534 per night
includes taxes & fees
NFL Draft Stay-Private Home Minutes from Acrisure Stadium-Sleeps 8- Park Free
Comfortable sofa
Living room
Beautiful bedroom space with storage
Kitchen fully equipped with essentials
Very good
(5 reviews)

3 BedHome in Upper Lawrenceville

Pittsburgh

8% off
NZ$5,897
for 7 nights, 1 home
NZ$842 per night
includes taxes & fees
3 BedHome in Upper Lawrenceville
Interior
Room
Interior
Interior
Exceptional
(6 reviews)

Lovely, cozy Beacon guest suite with portable kitchen in Squirrel Hill

Pittsburgh

6% off
NZ$2,523
for 7 nights, 1 room
NZ$360 per night
includes taxes & fees
Lovely, cozy Beacon guest suite with portable kitchen in Squirrel Hill
Living area
Living area
Private kitchen
Exterior
Exceptional
(16 reviews)

Home Away From Home • Minutes to Downtown

Pittsburgh

8% off
NZ$4,998
for 7 nights, 1 home
NZ$714 per night
includes taxes & fees
Home Away From Home • Minutes to Downtown
Living room with unique accent wall
Patio Balcony area with comfy couches and surrounded by trees and skyline
8-seater dining table in a cozy dining room
Kitchen with wooden cupboards and marble-designed countertops
Exceptional
(8 reviews)

Pittsburgh Gem - 5BR - Downtown Deck View

Pittsburgh

16% off
NZ$10,685
for 7 nights, 1 home
NZ$1,526 per night
includes taxes & fees
Pittsburgh Gem - 5BR - Downtown Deck View
Interior
Private kitchen
Living area
Room
Exceptional
(18 reviews)

Quick ride to the Stadiums!

Pittsburgh

8% off
NZ$4,594
for 7 nights, 1 home
NZ$656 per night
includes taxes & fees
Quick ride to the Stadiums!
Bright, airy living room with a 4K TV and a dining area, seating up to 6.
Striking art pieces provide pops of color and personality all over the unit.
The covered patio outside your unit provides a serene spot for morning coffee.
The living room features an eclectic mix of art pieces.
Exceptional
(18 reviews)

Luxe Design 3br in Pittsburgh's Most Lively Neighborhood

Pittsburgh

24% off
NZ$4,418
for 7 nights, 1 home
NZ$631 per night
includes taxes & fees
Luxe Design 3br in Pittsburgh's Most Lively Neighborhood
Exterior
Private kitchen
Dining
Terrace/patio
Exceptional
(5 reviews)

South Side Bicycle Home Sleeps 6

Pittsburgh

8% off
NZ$4,826
for 7 nights, 1 home
NZ$689 per night
includes taxes & fees
South Side Bicycle Home Sleeps 6
Outside seating area with charming environment
Beautiful Living room
Modern style kitchen
Entrance of the house
Very good
(6 reviews)

Enchanting 3BR with Yard | Patio

Pittsburgh

7% off
NZ$5,253
for 7 nights, 1 home
NZ$750 per night
includes taxes & fees
Enchanting 3BR with Yard | Patio
Dining
Exterior
Interior
Private kitchen
Exceptional
(5 reviews)

Thoughtfully furnished, comfortable, and convenient in Pittsburgh's East End.

Pittsburgh

9% off
NZ$3,089
for 7 nights, 1 home
NZ$441 per night
includes taxes & fees
Thoughtfully furnished, comfortable, and convenient in Pittsburgh's East End.
Living area
Exterior detail
Living area
Exterior detail
Exceptional
(5 reviews)

Family & Pet-Friendly Home w/ Fenced Yard & Office by Kennywood & The Waterfront

Homestead

8% off
NZ$4,002
for 7 nights, 1 home
NZ$572 per night
includes taxes & fees
Family & Pet-Friendly Home w/ Fenced Yard & Office by Kennywood & The Waterfront
Gold fish pond w/water spout is relaxing & calming - a real "zen" experience!
View of the opposite side of the patio in the morning shade.
Enjoy watching your favorite game/movie on the 55"smart LG TV.
Living Rm flows into Kitchen & Dining Rm. Enjoy entertaining guests!
Exceptional
(50 reviews)

3 BDRM●3 BATH●EV CHARGER ● ECLECTIC ● PATIO ●GARAGE ●PARKING● MIN TO DNTWN

Pittsburgh

8% off
NZ$9,044
for 7 nights, 1 home
NZ$1,292 per night
includes taxes & fees
3 BDRM●3 BATH●EV CHARGER ● ECLECTIC ● PATIO ●GARAGE ●PARKING● MIN TO DNTWN
Games room
Private kitchen
Outdoor dining
Living area
Wonderful
(58 reviews)

Charming Carnegie Cottage 15 Minutes from Airport & Downtown

Carnegie

7% off
NZ$2,083
for 7 nights, 1 home
NZ$298 per night
includes taxes & fees
Charming Carnegie Cottage 15 Minutes from Airport & Downtown
Chic Bar Cart Corner for Relaxing Evenings
A passion for what we do
Bright & Fully Equipped Modern Kitchen
Spacious Modern Kitchen with Open-Plan Dining
Very good
(5 reviews)

NEW! 3 Bdrm | Mt Washington | Garage

Pittsburgh

16% off
NZ$6,502
for 7 nights, 1 home
NZ$929 per night
includes taxes & fees
NEW! 3 Bdrm | Mt Washington | Garage
Private kitchen
Living area
Dining
Private kitchen
Exceptional
(36 reviews)

Hidden Gem in Swissvale sleeps 6

Pittsburgh

7% off
NZ$2,640
for 7 nights, 1 apartment
NZ$377 per night
includes taxes & fees
Hidden Gem in Swissvale sleeps 6
Interior
Property grounds
Private kitchen
Dining
Exceptional
(17 reviews)

Stylish King Suite w Deck & City Views • Free Off Street Parking

Pittsburgh

12% off
NZ$4,472
for 7 nights, 1 apartment
NZ$639 per night
includes taxes & fees
Stylish King Suite w Deck & City Views • Free Off Street Parking
  • 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. Acrisure Stadium and PPG Paints Arena are just a couple of the must-see attractions in the area. 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)
  • Kennywood (6.5 mi / 10.5 km)
  • Frick Park (3.8 mi / 6.2 km)
  • South Park Golf Course (7 mi / 11.3 km)
  • Boyce Park Ski Area (12.3 mi / 19.7 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)
  • North Park (12.5 mi / 20.1 km)
  • Gateway Center Park (1.8 mi / 2.9 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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