Holiday Homes in South Side

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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Holiday Homes in South Side

Stylish 4Bdr Loft Home, North Shore, City Skyline
TV, fireplace

Stylish 4Bdr Loft Home, North Shore, City Skyline

10.0 out of 10, Exceptional, (27)
"Would definitely stay again. No problems whatsoever Recommend"
The price is NZ$260
includes taxes & fees
11 Aug - 12 Aug
Stylish 4Bdr Loft Home, North Shore, City Skyline
Stylish & Central 3BD Home Pittsburgh/North Side
TV

Stylish & Central 3BD Home Pittsburgh/North Side

10.0 out of 10, Exceptional, (5)
The price is NZ$250
includes taxes & fees
28 July - 29 July
Stylish & Central 3BD Home Pittsburgh/North Side
Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside
Outdoor dining

Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside

6.0 out of 10, (3)
"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. "
The price is NZ$410
includes taxes & fees
28 July - 29 July
Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside
Urban Retreat with Garage on Mt Washington
Property grounds

Urban Retreat with Garage on Mt Washington

10.0 out of 10, Exceptional, (54)
"We loved staying on Mt Washington! It was close to everything we wanted to do. The house was clean, and a really easy walk to the grocery store, bakery, coffee shop, ice cream shop, and the incline."
The price is NZ$434
includes taxes & fees
20 Aug - 21 Aug
Urban Retreat with Garage on Mt Washington
Historic 4 Bed Northside Home - Amazing Location
Dining

Historic 4 Bed Northside Home - Amazing Location

7.2 out of 10, Good, (12)
"The property was exactly as expected, the pictures are very accurate. Property owner was very kind and responsive. Would definitely stay here again."
Historic 4 Bed Northside Home - Amazing Location
Not so tiny house with full kitchen & patio swing
View from property

Not so tiny house with full kitchen & patio swing

9.6 out of 10, Exceptional, (55)
"The home was great!!! Small and quaint! Perfect for us!!! "
The price is NZ$322
includes taxes & fees
4 Aug - 5 Aug
Not so tiny house with full kitchen & patio swing
Walkable Luxury 4 Br House
Exterior

Walkable Luxury 4 Br House

10.0 out of 10, Exceptional, (10)
"7 people stayed for 2 nights over New Years . We all enjoyed our stay. "
The price is NZ$580
includes taxes & fees
28 July - 29 July
Walkable Luxury 4 Br House
2 King Beds | Free Parking | BBQ | Arcade | Patio
Fridge, microwave, oven, stovetop

2 King Beds | Free Parking | BBQ | Arcade | Patio

9.8 out of 10, Exceptional, (23)
"Rented the house for one night and absolutely loved it. My son loved it the most, which is why I chose it. Would highly recommend!"
The price is NZ$539
includes taxes & fees
29 July - 30 July
2 King Beds | Free Parking | BBQ | Arcade | Patio
The Beverly at Mt. Lebanon by Luxe PGH
Full-sized fridge, microwave, oven, stovetop

The Beverly at Mt. Lebanon by Luxe PGH

4.0 star property
6.0 out of 10, (13)
"Beautiful place"
The Beverly at Mt. Lebanon by Luxe PGH
King Bed | Free Parking | Arcade | Fire Pit
Fridge, microwave, oven, stovetop

King Bed | Free Parking | Arcade | Fire Pit

2.0 star property
10.0 out of 10, Exceptional, (21)
"The parking and access for the property was excellent. We also like how close it was to the overlook/incline and stores and restaurants."
The price is NZ$548
includes taxes & fees
20 Aug - 21 Aug
King Bed | Free Parking | Arcade | Fire Pit
King Bed | Free Parking | Arcade | Fire Pit
Fridge, microwave, oven, stovetop

King Bed | Free Parking | Arcade | Fire Pit

10.0 out of 10, Exceptional, (12)
"Very easy to use and so many great amenities!"
The price is NZ$576
includes taxes & fees
20 Aug - 21 Aug
King Bed | Free Parking | Arcade | Fire Pit
Charming Carnegie Cottage 15 Minutes from Airport & Downtown
Fridge, microwave, oven, stovetop

Charming Carnegie Cottage 15 Minutes from Airport & Downtown

9.4 out of 10, Exceptional, (38)
"We had a fantastic stay in Pittsburgh! The property provided easy access to all the attractions we wanted to visit. It was a short trip to museums, PNC Park, and downtown, making it perfect for our sightseeing plans. The location was ideal, and the accommodations were comfortable and convenient. Highly recommend for anyone looking to explore the city!"
Charming Carnegie Cottage 15 Minutes from Airport & Downtown
1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area
Interior

1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area

10.0 out of 10, Exceptional, (20)
"Easy to locate. Comfortable bed. I would stay here again!"
1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area
Pittsburgh Home w/ Private Yard 3 Mi to Dtwn!
Fridge, microwave, stovetop, dishwasher

Pittsburgh Home w/ Private Yard 3 Mi to Dtwn!

9.8 out of 10, Exceptional, (35)
"We had a great time staying at this house. It was clean, accurately represented and in a great location!"
Pittsburgh Home w/ Private Yard 3 Mi to Dtwn!
2 Bedroom/ 2 Bath- 5 mins to stadiums - BEST city views - Free parking!
Fridge, microwave, oven, stovetop

2 Bedroom/ 2 Bath- 5 mins to stadiums - BEST city views - Free parking!

9.6 out of 10, Exceptional, (53)
"We had a great time in Pittsburg! House had wonderful views! We enjoyed our stay and communicating with the host was simple and timely!"
The price is NZ$990
includes taxes & fees
15 Aug - 16 Aug
2 Bedroom/ 2 Bath- 5 mins to stadiums - BEST city views - Free parking!
Gorgeous Southside Slopes home with outdoor hot tub and city view!
Smart TV

Gorgeous Southside Slopes home with outdoor hot tub and city view!

10.0 out of 10, Exceptional, (52)
"It was the perfect location for the bachelorette party. The house was clean and comfortable. Would definitely recommend! "
Gorgeous Southside Slopes home with outdoor hot tub and city view!
PGH City Home - Lovely 3 BR, 1.5 BA, Sleeps 7+ w/ Ultra Suited Location
Fridge, microwave, oven, stovetop

PGH City Home - Lovely 3 BR, 1.5 BA, Sleeps 7+ w/ Ultra Suited Location

10.0 out of 10, Exceptional, (29)
"We had a wonderful weekend in this beautiful home. The space is very comfortable and we were able to get to all the sites we wanted to see very easily. The hosts are fantastic! We will definitely be back!"
PGH City Home - Lovely 3 BR, 1.5 BA, Sleeps 7+ w/ Ultra Suited Location
Pet-Friendly Pittsburgh House: 3BR, Yard
3 bedrooms, desk, iron/ironing board, travel cot

Pet-Friendly Pittsburgh House: 3BR, Yard

10.0 out of 10, Exceptional, (3)
"We had a great time! Clean and as advertised!!! "
The price is NZ$750
includes taxes & fees
29 July - 30 July
Pet-Friendly Pittsburgh House: 3BR, Yard
Kids Centered House - Free Parking, Wifi, Fully Functional Kitchen.
Interior

Kids Centered House - Free Parking, Wifi, Fully Functional Kitchen.

2.0 star property
9.2 out of 10, Wonderful, (12)
"Very spacious and modern property. Even though you are in the downtown area of Pittsburgh, this location offers a quiet neighborhood with easy access to so many highways and attractions. Everything worked well and as advertised. Comfortable beds and room for everyone to have their own space. The host was responsive communicated effectively. I would stay here again and would highly recommend this location. "
Kids Centered House - Free Parking, Wifi, Fully Functional Kitchen.
Explore Pittsburgh from a Modern, Hip Bungalow
Terrace/patio

Explore Pittsburgh from a Modern, Hip Bungalow

9.6 out of 10, Exceptional, (48)
"This home is comfortable, nicely furnished, and decorated, clean, and very relaxing. Just what I wanted. "
The price is NZ$267
includes taxes & fees
27 July - 28 July
Explore Pittsburgh from a Modern, Hip Bungalow
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.
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Top South Side Hotel Reviews

EVEN Hotel Pittsburgh Downtown by IHG

EVEN Hotel Pittsburgh Downtown by IHG

10/10 Excellent
"This may be the best hotel I've stayed in and that's saying a lot! Super clean, the bed was comfortable. The mini workout station in the room was perfect! "
Christene 1-night trip
Posted 15 hours ago
EVEN Hotel Pittsburgh Downtown by IHG