Holiday houses in South Side Flats

Steel City of South Side Flats

This newly renovated gorgeous property with gated private parking is conveniently located in the middle of South Side. The house is everything you could want, allowing you easy access to the various neighborhoods and stadiums throughout the city, including Downtown, Oakland, PPG Arena, Acrisure Stadium, Pitt , Duquesne and more! You'll find the place cozy enough for a reset and recharge weekend, but also inspiring for gatherings and celebrations. One of the few places with gated private parking!

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

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!

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

King Bed, Artist's Flat

Kick back and relax in this calm, stylish space. Enjoy the evening around the fire pit or home theatre. 4 blocks to the exciting Riverfront and Southside Works stores, parks, restaurants and bars. 10 min. to Oakland or Downtown. The home has a newly remodeled kitchen, laundry and half bath on the main level. Upstairs is a spacious bedroom with a king bed, TV room, and a full bathroom. Out back is a lovely deck and Adirondack chairs around the fire pit. Perfect for a couple or young family.

Breathtaking South Side Loft / 2BedR - 1 Bath

Welcome to our one-of-a-kind loft in the vibrant South Side of Pittsburgh, where history and modern style blend seamlessly. Housed in a building with a rich past dating back to 1890, this ground-floor, loft-style walk-up is not just a place to stay but a journey through time. Once a speakeasy, our loft offers guests a unique experience that combines the charm of yesteryear with the comforts of today. Immerse yourself in the unique charm of a space where history meets contemporary comfort.

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!

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).

Perfect Pittsburgh 1BR Retreat | Food, Shops & Fun

Experience a stylish and modern 1BR stay in Pittsburgh, perfectly located near top restaurants, nightlife, and shopping. Enjoy a walkable neighborhood with easy access to local favorites like The Milkshake Factory and South Side BBQ Company. Relax at nearby Ormsby Park with green space and a pool. This cozy unit features fast WiFi, a full kitchen, and easy self check-in, making it perfect for couples, solo travelers, and business trips seeking comfort and convenience.

King Bed | Free Parking | BBQ | Fire pit | Arcade

✓ King Suite w/ Private Bath on ground floor ✓ Free parking ✓ 10 mins to Acrisure, PNC Park, PPG ✓ Arcade / BBQ / Fire Pit / Patio ✓ On Carson St - nightlife ✓ White noise machines Rank One Stays presents Carson Street Manor, an elegantly designed home located in the heart of South Side on Carson Street. You’ll be within walking distance to some of the best restaurants, nightlife, & entertainment that Pittsburgh has to offer.

Serenity on Jane

This place is not only within walking distance to all that the SouthSide Works has to offer which includes restaurants, stores and entertainment venues, but also a nearby grocery store. You will be a short drive from other main areas of Pgh such as Downtown, Oakland, where multiple universities and hospitals are located, and the North Shore which includes our stadiums and nearby museums!

Sarah St Rowhome - full kitchen & laundry

Welcome to our row home in the Historic Southside District. Recently remodeled, this 1 bedroom apartment will give you quick access to all of Pittsburgh’s neighborhoods. Take public transit, Uber, or walk to whatever you may have planned during your time in Pittsburgh. The apartment is equipped with everything you may need for however long your stay.