Family-friendly holiday rentals in South Side Flats

Townhouse in South Side Flats

The modern kitchen features white cabinetry, stainless steel appliances, and a spacious central island with yellow bar stools. Sleek countertops and stylish pendant lighting enhance the functional space, which is complemented by warm wooden flooring.

Amazingly Homey w/Garage + Outdoor Space! 5B/2B

Magnificent 5bedroom Southside townhome with private garage parking! Originally built in the early 1900s, the property recently underwent a full renovation which preserved it's character & charm, but added wonderful modern amenities. Located in one of the best locations in Pittsburgh, just a short walk to the Southside Strip. The property has a lovely outdoor patio with furniture and grill. It's a wonderful property for traveling business partners who want space, families, and small groups alike

4.88 out of 5 average rating, 308 reviews

Flat in Downtown Pittsburgh

Cultural District new King Suite whirlpool tub

Experience Pittsburgh's Cultural District from this new king suite! You are surrounded by Pittsburgh's best restaurants, shops, steps away from the Convention Center, theaters, and more. Designed for comfort and convenience in an unbeatable location. - King bed - Whirlpool tub / shower - Equipped Kitchen & Laundry - Walk to everything - Mult garages within 5 min - 24/7 guest support Perfect for business trips, events, or weekend getaways. We're here for you before, during and after your stay!

4.9 out of 5 average rating, 334 reviews

4.97 out of 5 average rating, 251 reviews

A spacious living area features a plush sectional couch positioned around a low coffee table. Light enters through a window dressed with blinds, highlighting the patterned area rug beneath. The wall is adorned with a large clock, adding a functional element to the room.

Flat in South Side Flats

Lovely South Side spacious 1 Bedroom with parking

Centrally located, 2 blocks from historic Carson street in the heart of the South Side. Restaurants, bars, shopping, bus transportation just outside the front door. Convenient to all Pittsburgh sports venues/theater district. Apartment is fully equipped with all kitchen amenities, a spacious bedroom and bath. New tiled shower installed January ‘23. Work space provided. A/c provided in the summer. Small on site reserved parking space makes this a rare find! 4.8 guest rating required to book

4.95 out of 5 average rating, 163 reviews

A spacious living area features large windows adorned with deep red curtains, allowing natural light to filter in. Comfortable seating options include two armchairs and a plush sofa, all set around a coffee table. A colorful area rug adds warmth to the space.

Flat in South Side Flats

South Side Cool in the Heart of the Flats

Our home in the heart of the historic South Side Flats neighborhood, is a five minute drive to revitalized downtown Pittsburgh. Our location offers easy access to all Pittsburgh sports stadiums, the Riverfront Trail and great shopping. Only 10 minutes to all major universities and medical institutions in Oakland. Near major parks and museums. Our first floor, 5 room suite sleeps up to 4 guests with kitchen, 1.5 bathrooms, & small garden. Steps away from Pittsburgh's most exciting neighborhood!

A six-person hot tub is set in a private outdoor area, surrounded by a white wooden fence. Gentle water jets create ripples in the clear blue water. Potted ferns hang from the fence, adding a touch of greenery to the tranquil space.

4.97 out of 5 average rating, 197 reviews

Pittsburgh's Tropicana w/ outdoor hot tub

Family owned and managed, immaculate high end, tropical inspired home located on the historic Southside. Only 3 blocks from Carson Street Close to downtown (2.8 miles) universities, sport/concert venues(3.9 miles) Keep your cars safely parked in our huge driveway with security camera! No need to drive around looking for spaces! Fantastic outdoor area with grill and jacuzzi! It's like you are in your own private little resort *Check out our other 5 star house Gorgeous Southside Slopes House*

A front porch is featured, with wooden railings and two chairs facing a small table. A large window offers a view into the interior space, while nearby siding presents a neutral tone. Greenery is noted at the base of the porch posts.

4.94 out of 5 average rating, 213 reviews

UPSCALE HOME CENTRALLY LOCATED IN SOUTH SIDE FLATS

Centrally located in South Side Flats, many of the most popular S. Side restaurants & bars are a few minutes walk away. The stadiums/arenas are also only a short drive. The home has 1.5 bathrooms & 2 bedrooms (queen bed in each room plus a futon in 2nd BR). Features include air conditioning, 1st floor washer/dryer, private back patio, front porch, & kitchen basics for cooking. I can only register 1 car for parking & it's on-street parking only. There are no assigned spots; 1st come, 1st serve.

The kitchen features warm wood cabinetry and stylish granite countertops. A large dining table with multiple chairs is positioned in the center. Natural light is provided by a glass door leading to an outdoor space. An elegant staircase with decorative iron railings is visible in the background.

4.99 out of 5 average rating, 105 reviews

Steel City Retro - Walk to 50+ Restaurants & Pubs

New listing of a totally renovated house, 1 block off historic East Carson Street in Pittsburgh's SouthSide, the entertainment capital of the city. Walking distance to PPG ARENA, many restaurants, shopping and more. 2.2 miles from HEINZ FIELD and the Convention Center. This is a 4 bedroom (4 twin, 2 full, 1 queen bed + sleeper sofa)/ 3 bath home. 1st floor is disability friendly and has an integral 1 car garage. NEED MORE BEDS? Try SOUTH SIDE SPACIOUS - 7 beds + 1 queen sofa + 1 futon.

The exterior of a brick building is showcased, featuring a combination of red and beige tones. Planters with greenery are positioned under the windows, and climbing vines add texture to the façade. Steps lead to a welcoming entrance adorned with a canopy.

4.99 out of 5 average rating, 140 reviews

Beautifully Restored Home in a Historic District

Experience the best of Pittsburgh's vibrant South Side, right outside your door. This prime location in the Historic District puts you within easy walking distance of everything, from the bustling shops and restaurants of East Carson Street and South Side Works to the scenic Great Allegheny Passage. Enjoy access to all major Pittsburgh amenities, with numerous dining, entertainment, and shopping options just steps away. Off-street and garage parking is available for your convenience.

Townhouse in South Side Flats

The living room features bold teal walls and large windows, allowing natural light to fill the space. A comfortable gray sofa is adorned with decorative pillows, complemented by a gold coffee table atop a textured black rug. Stylish curtains frame the windows, enhancing the inviting atmosphere.

Colorful Southside gem! Off-street parking!

Great 2 story, 2 bedrooms apt located just a few blocks up from the South Works! Tons of shopping, restaurants, bars & coffee shops nearby! The space is bright, colorful & travel-themed. Fully outfitted for short or long term rentals, with plenty of charm & style to make you feel right at home. 2 bedrooms feature 1 King, 1 Full & living room has 1 sofa that lays flat as a twin-sized bed, sleeping 5 comfortably! Eat-in kitchen has new appliances & seating for 4! Ideal location!

4.86 out of 5 average rating, 293 reviews

A modern living area is highlighted by large windows allowing natural light to fill the space. A comfortable sofa is adorned with decorative pillows, facing a wooden coffee table. A tall lamp stands nearby, and shelves display various books and decor.

4.91 out of 5 average rating, 447 reviews

Urban converted gas station in heart of South Side

My place is close to art and culture, restaurants and dining, and family-friendly activities. The southside is loaded with bars and restaurants, grocery and clothing stores, galleries, public library and pool. It is very near downtown Pgh and has great bike/running trails along the river. You’ll love my place because of the outdoors space, the neighborhood, the light, the comfy bed, and the kitchen. My place is good for couples, business travelers, and furry friends (pets).

An open kitchen and living area feature wooden cabinetry and stainless-steel appliances. A central island with bar stools provides additional dining space. Natural light floods the room through windows, highlighting the raised tin ceiling and hardwood floors.

5.0 out of 5 average rating, 246 reviews

High-End South Side 4 Bedroom House, sleeps 15!

Newly Remodeled, Gorgeous High-End 4 Bedroom, 3 Full Bathroom entire house in the heart of Pittsburgh's historic South Side neighborhood; SLEEPS UP TO 15 PEOPLE; Pets welcome; Private/Enclosed Patio Hardwood floors, raised tin ceilings on first floor; open floor plan living room/kitchen with stainless-steel appliances, marble-counter-tops, Keurig, 70 inch TV, WiFi, Convenient 2nd floor laundry facilities,HD Televisions in every bedroom w/ Cable, Luxurious Memory Foam Beds