Holiday rentals with outdoor seating in South Side Flats

4.94 out of 5 average rating, 216 reviews

A functional kitchen features grey cabinets complemented by wooden countertops. Open shelves display various glassware and kitchen essentials. A large sink with a dish drying rack is visible, alongside modern appliances, including a stainless steel refrigerator and coffee maker. Natural light enters through a window with blinds.

Home in North Side

Pittsburgh, PA - North Side

Keep it simple at this peaceful and centrally-located place. This two bedroom single family home is in an optimal location for access to all Pittsburgh has to offer. Located 2 miles from Pittsburgh's downtown area and Strip District, 5 minutes from PNC Park and Heinz Field, 10 minutes from PPG Paints Arena and UPMC Hospitals, and 15 minutes from CMU, University of Pittsburgh, and Duquesne University. Minutes from Garden Cafe coffee shop, Threadbare Cider House and plenty of bars and restaurants.

An open living area showcases modern furnishings, including a cozy gray sectional sofa with decorative cushions. A striped area rug covers the floor, while a wooden coffee table holds small plants. A staircase with black railings leads to the upper level, and dining space is visible in the background.

4.95 out of 5 average rating, 251 reviews

New Home with an integral garage and rooftop deck!

New construction home located in the desirable Southside flats area. Home comes with an integral tandem style garage for parking (2 cars can park back to back inside the garage) You’ll love hanging outside on the rooftop deck and being able to see different views of the city of Pittsburgh! Countless restaurants, bars, and stores are within walking distance. Close drive to the PPG Arena. Short drive to PNC Park, Heinz Field, Rivers Casino, and local museums. Minutes away from downtown Pittsburgh!

An aerial view captures the contemporary home surrounded by lush greenery. The structure showcases a mix of wood and metal siding, with a spacious deck featuring outdoor seating and dining options, as well as a grassy area below, inviting relaxation amidst nature.

4.99 out of 5 average rating, 177 reviews

Cliffside Luxury with Spectacular City Views

Amazing views, rooftop patio w/fire pit, contemporary design and furnishings are just the beginning for your amazing stay at our cliffside paradise. This architecturally stunning home offers a fully equipped kitchen, two decks to dine and relax on. Beyond its walls, you can visit the nearby Station Square shops and restaurants, 2 Inclines, Pittsburgh Zoo and PPG Aquarium, Warhol Museum, the Rivers Casino, or watch the Penguins at PPG Arena, Steelers at Heinz Field, and the Pirates at PNC Park!

4.97 out of 5 average rating, 212 reviews

A retro-inspired kitchen is equipped with mint green appliances and sleek white cabinetry. Countertops are complemented by a backsplash of white tiles, while natural light enters through a window with horizontal blinds. A dining table is positioned nearby, enhancing the kitchen's functionality.

Bungalow in Carnegie

Groovy Retro Get-Away

With a retro flare & a mid-century modern vibe, you'll enjoy this quaint bungalow in a quiet residential neighborhood conveniently located minutes from downtown Pittsburgh, the airport, many great sites, must-see attractions, universities & colleges. Whether you're in town for business, a sports event, bringing a student back to school or just want some time away, this cozy space is perfect! Everything in this bungalow is well appointed including keurig coffee, WiFi & a smart TV for streaming.

Apartment in Mount Washington

A living area features a comfortable couch, accent chairs, and a stylish coffee table on a patterned rug. Large windows provide natural light, framed by bright curtains. A lamp adds warmth, and modern artwork is displayed on the wall, enhancing the vibrant space.

4.97 out of 5 average rating, 165 reviews

Grandview Balcony w/ Stunning Skyline Views

One of the few places to stay on Grandview Ave, the famous road with million dollar views in Pittsburgh! Completely remodeled in November 2022, our place exudes Pittsburgh charm. Sit on the balcony with a beverage, or relax on the comfy couch and take in the city skyline. Cook something in our spacious kitchen, or stroll a block to Shiloh St., with 10+ bars & restaurants! The incline to Station Square is a block away, or use your vehicle (parked in our private lot). You can't beat these views!

Apartment in East Liberty

The bedroom features a spacious bed covered in crisp white linens, highlighted by a blue accent throw. Blue curtains frame multiple windows, allowing natural light to fill the room. A small desk and chair are positioned nearby, complemented by a decorative plant and wall art.

4.98 out of 5 average rating, 159 reviews

Upscale King Bed Suite |ADA w/ Free parking!

Enjoy our spacious king-sized bed suite located in the safe, central Friendship neighborhood. This newly renovated retreat is just a short distance from all that Pittsburgh has to offer! Steps away from Whole Foods and short walk to Yinz Coffee shop! ⭐King bed (Memory foam mattress) ⭐Queen pull out bed ⭐Pack n play ⭐ADA Accessible! ⭐In-unit washer/ dryer ⭐Large desk w/ speedy wifi & extra monitor ⭐Pet friendly ⭐24/7 Guest support ⭐Free off-street parking ⭐Close to CMU/ Pitt! ⭐$0 cleaning fee!

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.

4.95 out of 5 average rating, 202 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 suite in Highland Park

The exterior of a sunporch suite is displayed, featuring large wall-to-wall windows framed by white columns. A pathway leads to the entrance, surrounded by lush greenery, including a bush. The home showcases a charming blend of white and red brick, adding character to the facade.

4.98 out of 5 average rating, 285 reviews

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

Apartment in Lower Lawrenceville

The living area features a blue three-seater couch with a round rug underneath, paired with a coffee table. A kitchen island with bar stools is visible in the background, while a dining table and wooden stairs leading to an upper level are seen on the right. Natural light enters through nearby windows.

4.94 out of 5 average rating, 222 reviews

Brand New! Lawrenceville KING Suite - Huge Balcony

1 bedroom 1 bath apartment w/ a HUGE private balcony steps from Butler St in Lawrenceville neighborhood! Sleeper Sofa and extra linens for bigger groups. BRAND NEW construction! Enjoy this stylish space in the coolest neighborhood in town, steps to dozens of restaurants, shops, coffee shops. A few blocks to UPMC Children's hospital and the Strip District, short drive to Downtown, North Shore, Shadyside, Oakland, very close to Pitt, CMU, & several hospitals! Book your stay today!

The living room features a comfortable gray sofa adorned with colorful cushions, complemented by a soft area rug with bold geometric patterns. Natural light enters through windows, illuminating a TV stand with a large screen. A decorative ottoman and a chair add to the inviting space.

4.95 out of 5 average rating, 105 reviews

Cozy, Pet-Friendly Home in Pittsburgh South Side

Welcome to Steel City! Our updated two-bedroom house in the lively South Side is a perfect home for your group to relax and unwind including your four-footed friends! After exploring the city, enjoy the mood lighting on our cozy patio or check out the local restaurants and bars within walking distance. Work from home with a desk space in each bedroom. Our home has everything you will need and a perfect location if you're looking to have a truly authentic Pittsburgh experience!

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, 414 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).

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.

4.88 out of 5 average rating, 171 reviews

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

Popular amenities for South Side Flats outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.85 out of 5 average rating, 62 reviews

A modern kitchen features sleek cabinetry and a spacious wooden island with three black bar stools. Stainless steel appliances, including a refrigerator and oven, are visible, alongside a mosaic backsplash enhancing the kitchen's contemporary style.

Home in South Side Flats

House 3bed Free Parking Walk to Bars & Shops

Superhost

4.83 out of 5 average rating, 86 reviews

Large 1BR on hill close to everything in Pitt

4.99 out of 5 average rating, 102 reviews

A spacious living area features high ceilings and natural light from large windows. A cozy gray couch and teal armchair are paired with a decorative coffee table on a textured area rug. A marble fireplace adds a classic touch, while a ceiling fan enhances airflow.

Home in Bellevue

Grand on Grant

4.94 out of 5 average rating, 84 reviews

The living room features a comfortable leather sofa, two modern chairs, and a coffee table. A cozy fireplace is framed by light-colored tiles. Lush greenery and decorative art pieces add visual interest, while warm wooden flooring enhances the inviting atmosphere.

Home in South Side Flats

King Bed, Artist's Flat

A private rooftop deck features a central fire pit with flames dancing above decorative stones. Surrounding the fire pit are various potted plants filled with vibrant flowers. The city view includes nearby buildings and a street, framed by a black railing.

5 out of 5 average rating, 50 reviews

Little Red Cat/Historic CoffeeCozyParking/PITT/CMU

4.95 out of 5 average rating, 116 reviews

A dining area features a wooden table surrounded by six black chairs. Natural light filters in from a window with a cozy seat and decorative pillows. Framed artwork is displayed on the wall, enhancing the minimalist design.

Home in Mount Washington

Steel City Retreat- 2 Bedroom house with Parking

4.96 out of 5 average rating, 74 reviews

A welcoming living room features a blue sofa and two comfortable chairs arranged around a circular coffee table. A stone fireplace with decorative accents is the focal point, complemented by shelves displaying artistic decor. Natural light enters through the windows, enhancing the space.

Home in South Side Flats

Stunning Views + Roof Deck | Free Parking

A modern bathroom features dual circular mirrors above a spacious white sink vanity. A large slate shower with a glass enclosure includes a rainfall showerhead. Light colored tiles cover the floor, while a black metal shelving unit holds neatly arranged towels.

4.96 out of 5 average rating, 67 reviews

Entire Home * Lux Master * Terraces * 4-Car

Apartment rentals with outdoor seating

4.98 out of 5 average rating, 121 reviews

The exterior of the red-brick duplex features a rounded entrance with a decorative arch and a blue front door. Symmetrical windows on either side are framed with shutters. A small staircase leads up to the entrance, which is set amidst a well-maintained outdoor area.

Apartment in Pittsburgh

A Retreat Above It All

4.95 out of 5 average rating, 150 reviews

The living room features a spacious grey sofa adorned with a navy throw blanket. A blue and cream patterned rug covers the hardwood floor, while natural light streams through sheer white curtains. A light fixture and a small side table complete the serene ambiance.

Apartment in Pittsburgh

Newly remodeled 2 bedroom apartment

4.86 out of 5 average rating, 260 reviews

A living area is displayed, featuring a red sofa and a small black coffee table centered on a patterned rug. A wall-mounted television is visible, and a doorway leads into a room in the background. Soft lighting enhances the cozy ambiance.

Apartment in Pittsburgh

Cuddys Place

Apartment in Mount Washington

A panoramic view of Pittsburgh's skyline is captured, showcasing a blend of modern skyscrapers alongside green hills. The Monongahela River is visible, with tree-covered slopes in the foreground and rooftops of nearby homes positioned on a hillside.

4.99 out of 5 average rating, 138 reviews

Mt Washington Best View! Pittsburgh Luxe Apartment

Apartment in Squirrel Hill North

A well-equipped kitchen is highlighted by modern appliances, including an oven and a refrigerator. A wooden dining table with four chairs offers a space for meals. Natural light floods the area through large glass doors leading to an outdoor patio.

4.97 out of 5 average rating, 859 reviews

Spacious, warm, private apartment near CMU /Pitt

4.97 out of 5 average rating, 185 reviews

The open-concept living area features modern design elements, including a kitchen island with granite countertops, a sofa positioned beside a decorative wall, and natural light entering through nearby windows. Wooden flooring contrasts with gray tiles, and a circular mirror adds a stylish detail.

Apartment in Shadyside

Walk to CMU, Pitt, Shadyside! King Suite! Parking!

Apartment in East McKeesport

The living room features a light-toned sofa and a blue couch, complemented by a dark coffee table. Two lamps provide soft lighting, while a ceiling fan adds comfort. A window allows natural light to fill the space, framed by white blinds.

4.93 out of 5 average rating, 384 reviews

Quiet Luxury Apartment!

Apartment in Central Northside

A spacious living area features a large flat-screen TV mounted above an electric fireplace. A coffee table is positioned centrally, while large windows allow natural light to illuminate the room. Potted plants enhance the inviting atmosphere of the space.

4.95 out of 5 average rating, 183 reviews

Amazing views! Free Parking!

Condo rentals with outdoor seating

Condo in Mount Washington

A dining area is positioned by large windows, allowing natural light to fill the space. A round table is surrounded by four chairs, and a potted plant is at the center. A modern kitchen with stainless steel appliances is visible in the background, enhancing functionality.

4.87 out of 5 average rating, 195 reviews

Luxury Grandview Ave Cozy Gem (2bed/2bath)

4.95 out of 5 average rating, 42 reviews

A sectional sofa with throw pillows is positioned around a white coffee table, which holds a decorative item. A lamp provides soft lighting, and framed wall art enhances the space. The room is painted in a muted green tone, contributing to a comfortable ambiance.

Condo in Knoxville

Sleeps up to 10! Large Condo w/ 6 Beds + WIFI!

Condo in Mount Washington

Outdoor seating is provided on a deck, featuring two wicker chairs with deep blue cushions and a glass-top coffee table. Panoramic views of the Pittsburgh skyline and river are visible in the background.

4.94 out of 5 average rating, 516 reviews

Luxury Pittsburgh Grandview Ave Apt