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

Indoor spacesKitchenHospitality

4.88 out of 5 average rating, 313 reviews

Apartment 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!

KitchenFamilyGetting around

4.9 out of 5 average rating, 373 reviews

Apartment in South Side Flats

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.

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!

FamilyIndoor spacesAccuracy

4.95 out of 5 average rating, 163 reviews

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, 215 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.

FamilyKitchenLong stay

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!

KitchenIndoor spacesBathroom

4.86 out of 5 average rating, 295 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.

4.9 out of 5 average rating, 449 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).

FamilyKitchenBackyard

Superhost

A spacious rooftop deck showcases a comfortable seating area with plush cushions and a coffee table, overlooking a vibrant cityscape. A large umbrella provides shade, while the surrounding rooftops are illuminated by soft evening light.

Loft in South Side Flats

Skyline Views | Rooftop & Game Room | Sleeps 8!

Stunning 2BR apt in South Side, sleeps 8. High-end kitchen, arcade room, and massive rooftop deck with panoramic views of Pitt. Ideal for families! Book now to experience best view in town! ✔ 4 Comfortable Queen Beds ✔Massive Balcony Overlooking The City ✔Fun Arcade Room With Air Hockey, Board Games, and Pac Man ✔ Fully Equipped Modern Kitchen With Amazing View Of Pittsburgh ✔ Professionally Cleaned and Sanitized ✔ Free Street Parking ✔ Free Keurig Coffee Learn more below!

Indoor spacesKitchenParking

4.85 out of 5 average rating, 106 reviews

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, 247 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

KitchenFamilyCleanliness

Townhouse in South Side Flats

Exquisite 4Bed/3.5Bath Home W/Garage +Rooftop Deck

Sensational and brand spanking new! 4Bedrooms/3.5 bathrooms, GARAGE PARKING , and a wonderful roof deck to unwind and enjoy! Bedrooms consist of 2x queen beds, 1x full bed, 2x queen futons, capable of sleeping 10 comfortably. Garage parking for 1 vehicle! Grill included. Amazing South Side location just a short distance to all attractions Pittsburgh has to offer. It's a wonderful property for traveling business partners who want space, family getaways, and group travelers

FamilyIndoor spacesSleep quality

4.83 out of 5 average rating, 277 reviews

Superhost

A spacious deck features outdoor seating, including a dining table and lounge chairs. The view overlooks the skyline of downtown Pittsburgh and the surrounding lush greenery, providing a serene outdoor space for relaxation.

Home in Pittsburgh

Breathtaking View of Pittsburgh! 3bd, king suite!

Wow! Enjoy Pittsburgh’s charm at this upscale home with spectacular views of downtown, nestled on a quiet hill in an ideal location a short drive from nearby attractions. A wonderful combination of professional design and modern amenities makes this the perfect place to stay whether you're traveling for work or pleasure. 6 Min Drive to Mount Washington 9 Min Drive to Phipps Conservatory & Botanical Gardens 9 Min Drive to PNC Park

Indoor spacesKitchenHiking

4.85 out of 5 average rating, 197 reviews

4.97 out of 5 average rating, 373 reviews

Spacious Modern Home • Rooftop Deck

Rest easy in Pittsburgh’s historic South Side Flats—steps from top restaurants, shops, and nightlife. Walk to South Side Works, riverfront trails, and the GAP, or use transit for quick access to Downtown, stadiums, and Oakland. This spacious, professionally managed home is perfect for groups, featuring a large living area, full kitchen, fast WiFi, deck with grill, and comfortable beds. Free garage and off-street parking included.

Indoor spacesKitchenAmenities

Superhost