Holiday rentals in South Side Flats

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Top-rated holiday rentals in South Side Flats

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Top guest favourite
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 Pittsburgh
4.96 out of 5 average rating, 215 reviews

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

Guest favourite
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 Pittsburgh
4.95 out of 5 average rating, 160 reviews

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!

Top guest favourite
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.
Home in Pittsburgh
4.95 out of 5 average rating, 204 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.

Guest favourite
A spacious living area features a navy blue couch and a large coffee table on a decorative area rug. Two lamps provide soft lighting, while a mirrored accent wall enhances the room's openness. The dining area is visible in the background, with a large table and chairs.
Flat in Pittsburgh
4.85 out of 5 average rating, 777 reviews

South Side Flats - Central to everything!

Artfully decorated, large, and open concept 1 bedroom apartment in the center of the South Side Flats entertainment district. Everything you need is within steps of your front door - restaurants, grocery, and entertainment. 5 min from downtown & within 15 min to anywhere in the city. IMPORTANT: This listing is exclusively for people visiting Pittsburgh. DO NOT book with us if you live in Allegheny County without 1st receiving permission from the host, or your reservation will be cancelled.

Guest favourite
Apartment in Pittsburgh
4.91 out of 5 average rating, 175 reviews

Sleek Apt in the Heart of Downtown| Stunning views

Welcome to Pittsburgh!! Stay in our newly remodeled luxury downtown apartment! This home has the most spectacular view and is located in the center of downtown Pittsburgh, nestled just across from the beautiful hotels of downtown! Offering top-tier amenities, and today’s modern conveniences. Ideally situated minutes from Pittsburgh's best shopping, stadiums, convention center and restaurants. Our intimate 1 bedroom home is comfortable and secure for family, friends and business people alike.

Guest favourite
A modern living area features large windows offering expansive views of the city skyline. A sectional sofa is positioned around a low coffee table, with a television mounted on the wall. Natural light fills the space, highlighting the hardwood flooring and contemporary decor.
Home in Pittsburgh
4.95 out of 5 average rating, 476 reviews

Spectacular Skyline Views - Luxury 2 Bedroom

Watch the city skyline buzz from the comfort of your couch or bed. This high end luxury home is located on Mt. Washington and close to everything Pittsburgh. Minutes walk to Southside, Downtown, Strip District, Heinz Field, and PPG Convention Center just to name a few. Super clean, comfortable, and cool with all of the amenities of your own home. Just bring your bag and make this home base while you're in the Burgh. Great for couples, friends, solo adventurers, and business travelers.

Top guest favourite
The open living area features a stylish kitchen with stainless steel appliances and a comfortable seating area with a blue couch. Large windows allow natural light to fill the space while offering city views.
Apartment in Pittsburgh
4.96 out of 5 average rating, 304 reviews

Free Parking!★ Private Gym★ Great Views!

Luxury living downtown! Whether you're staying for a few days or a few months, you'll love the location and amenities of our apartment! ➤ Our fourth floor apartment features city views from huge windows (with motorized blinds) ➤ Relax in the multi-jet shower & jetted tub ➤ Park for free in the attached underground garage ➤ Work out in the free fitness centers ➤ Work from home at your desk with 400mbps fiber internet ➤ Smart TVs in bedroom + living room Questions? Don't hesitate to ask!

Top guest favourite
A vintage desk is positioned by large windows adorned with golden curtains, allowing natural light to fill the space. A cozy ergonomic chair complements the desk, while a decorative globe and a small flower arrangement add character. The city skyline is visible through the window.
Flat in Pittsburgh
4.97 out of 5 average rating, 165 reviews

Grandview Ave - King Bed - Spectacular Views!

One of the few furnished rentals on Grandview Ave, the famous road with million dollar views in Pittsburgh! Completely remodeled to the studs as a short-term rental, our place exudes Pittsburgh charm. Work from home with spectacular views of the city from your vintage desk, relax on the couch and watch the 60" TV, or just hang out on the king size bed! We're just a block from Shiloh St., with 10+ bars & restaurants, but you're always able to cook at our fully stocked kitchen!

Guest favourite
A welcoming living area features a rustic brick fireplace and a mounted flat-screen television. Two stylish brown chairs are positioned beside a black coffee table, while a dining space is visible in the background, complete with a modern kitchen layout.
Townhouse in Pittsburgh
4.79 out of 5 average rating, 199 reviews

Homey & Perfectly Located 3BR/2BT - Sleeps 8!

Comfortable, homey and welcoming - Our peaceful and centrally-located property is wonderful for small groups. Open concept living + amenities like a game room to help you rest, relax, and unwind. 3 bedrooms/4 beds + 2 full bathrooms to comfortably sleep 8! South Side location just a short distance to all attractions Pittsburgh has to offer, yet quiet in the evenings. Wonderful property for traveling business partners who want space, family getaways, and small group travelers.

Top guest favourite
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.
Home in Pittsburgh
4.91 out of 5 average rating, 420 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).

Guest favourite
The exterior of a charming three-story house is presented, featuring a white facade with gray trim. Large windows allow natural light to fill the space. A covered porch with white railings is visible at the entrance, providing access to the front door.
Home in Pittsburgh
4.91 out of 5 average rating, 114 reviews

Contemporary and beautiful 1 bedroom unit

This lovely place has a style of its own. Contemporary living at its best! It is Conveniently located in Mt Washington on the bus line, walking distance to the trolly, and close to all major highways; you won’t have any issues getting around. Comes with both on and off street parking, brand new stainless steel appliances in the kitchen including a dishwasher. New furniture. Large new smart flat screen TVs in the bedroom and living room. This place is definitely a must!

Superhost
Flat in Pittsburgh
4.84 out of 5 average rating, 410 reviews

Uptown Apartment - right up from Pittsburgh!

**PLEASE BE HONEST ABOUT THE NUMBER OF GUESTS** *Pets are welcome! One time $40 pet fee* Uptown is a mixed residential & commercial area that’s right up from downtown Pittsburgh! It’s up and coming, a unique neighborhood that has all the benefits of being near the heart of the city! The apartment is close to the city center, art and culture, and public transport. You’ll love my place because of the location, coziness, and cleanliness. All types of travelers welcome!

Popular amenities for South Side Flats holiday rentals