Holiday rentals with outdoor seating in Shadyside

Find and book unique rentals with outdoor seating on Airbnb

Top-rated rentals with outdoor seating in Shadyside

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Guest favourite
A nighttime view of Pittsburgh showcases a vibrant cityscape, with twinkling lights illuminating the skyline. The sloped foreground provides a natural boundary, creating a contrast against the urban setting. The scene captures the essence of life in a historically rich neighborhood.
Home in South Side Slopes
4.92 out of 5 average rating, 132 reviews

*z 2231 1BR Southside *Sloped* Home Close to Pgh

Quirky South Side Slopes home convenient to Pittsburgh and all local attractions. This property is located in one of Pittsburgh's original industrial neighborhoods which is remaking itself into a fun vibrant community. With fun views from high above the city this neighborhood was home to many Pittsburghers who worked in the steel mills that helped build our great nation. Come get a feel for the way Pittsburghers used to live and enjoy everything Pittsburgh has to offer today, yinzer approved!

Top guest favourite
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
4.94 out of 5 average rating, 216 reviews

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.

Top guest favourite
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
4.97 out of 5 average rating, 212 reviews

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.

Top guest favourite
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.
Guest suite in Highland Park
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.

Top guest favourite
An open living space features a modern kitchen with stainless steel appliances, a dining area with two stools, and a cozy seating arrangement with a brown couch and decorative pillows. A large window allows natural light to fill the area, complemented by sleek laminate flooring.
Flat in Shadyside
4.97 out of 5 average rating, 140 reviews

Cozy King Suite Just off Walnut

In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 1BR/1 bath apartment in a prime location, with all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted & entirely remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances & in-unit laundry is brand new!

Guest favourite
A living room features comfortable seating, including a dark leather couch and a vintage blue chair. Shelves line the walls, displaying decor and plants. A warm rug sits on the wooden floor, complemented by natural light filtering through sheer curtains.
Home in Garfield
4.91 out of 5 average rating, 134 reviews

Bright Garfield rowhome with fenced-in yard

Walk to anything you need from this cozy, bright rowhome in Pittsburgh's Garfield neighborhood! Best for couples or remote workers, but can accommodate up to four guests. The second bedroom doubles as a workspace. There is a fenced-in backyard for guest use. 5-minute walk to Penn Ave bars, shops, restaurants, grocery stores & more. Convenient access to bus lines & surrounding neighborhoods of East Liberty, Shadyside, Bloomfield, Oakland, Lawrenceville, Highland Park, & the Strip District.

Guest favourite
A spacious bedroom is illuminated by natural light from multiple windows. A wooden bed with a luxurious mattress is centered, complemented by bedside lamps. A cozy seating area features a circular chair, and a decorative rug adds color to the hardwood floor.
Flat in Shadyside
4.94 out of 5 average rating, 104 reviews

Shadyside/Central @5 Stylish&Bright Studio w/Prkg

Modern and Stylish family oriented bright Studio apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment a Studio with bathroom, kitchen and FREE Parking. Stylishly setup, our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families, executives, expats and this is NOT a party place.

Guest favourite
The living area features a cozy green couch adorned with plush cushions and a warm throw. A circular coffee table sits in front, while a vintage fireplace adds character. Natural light pours in through large windows, draped with elegant curtains.
Flat in Bloomfield
4.95 out of 5 average rating, 99 reviews

Art Deco House In Prime Location

Step back in time and experience the charm of old-world glamour in this stunning 4 bedroom, 2 bath art deco style apartment. This unique and spacious home boasts an abundance of natural light and charming details. Located in the heart of Bloomfield, putting you just steps away from some of the best restaurants, shops, and nightlife in the city. Whether you're here for a romantic getaway, a family vacation, or a fun-filled city break, this apartment provides the perfect base.

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 East Carson Street
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).

Top guest favourite
The bedroom features a queen bed adorned with a colorful quilt, flanked by bedside tables. A window with sheer curtains allows natural light, and a ceiling fan provides airflow. A cozy seating area includes an armchair, and artwork decorates the green walls.
Flat in East Liberty
4.93 out of 5 average rating, 216 reviews

Private East Liberty Flat

Private one-bedroom flat in renovated East Liberty row house. Great central location. Walking distance to parks, shops, restaurants. Easy access to public transportation. Queen bed. Dining/desk area. Full kitchen with electric range, dishwasher, refrigerator, coffee maker, kettle, toaster and a microwave. Filtered cold water in fridge. Wireless internet. Radiant floor heating. Window air conditioning. Private entrance with keypad lock. Hosts live n

Guest favourite
A colorful living area features a bright blue wall that enhances the lively atmosphere. An orange sofa is paired with a textured throw, while shelves display kitchen amenities. A compact washer and dryer are built into the kitchenette, and natural light filters through the window.
Tiny home in Lower Lawrenceville
4.93 out of 5 average rating, 127 reviews

Le Petit Riad: A Moroccan Oasis

Le Petit Riad, "The Little Courtyard" in French, is an immersive Moroccan experience. Inspired by Chefchaouen, the sapphire colored city, this is a tiny space with big IMPACT. Every meticulous detail will leave you wondering if somehow, magically, you ended up on a flight to the Mediterranean, instead of PIT. Nestled in a quiet alley literally steps from Butler Street and all Lawrenceville, the hottest hood in Pittsburgh, has to offer.

Guest favourite
The bedroom features a spacious king bed with a memory foam mattress, accompanied by a plush blanket. A large window allows natural light to fill the room, complemented by stylish curtains. An office desk with a chair and a lamp are present, along with a closet and bedside table.
Flat in Shadyside
4.84 out of 5 average rating, 282 reviews

🔥Pristine King Bed Suite ⚡️ Hidden Gem 💎 PITT / CMU ✨ Pet Friendly 🐶

Pristine 1 bedroom apartment in the heart of Shadyside! Prime location, short walk to plenty of restaurants, shops, coffee shops & UPMC Shadyside hospital! Fully equipped for both long and short stays. 🔹King bed (memory foam mattress) 🔸Pet friendly! 🐶 🔹Fully stocked & equipped kitchen 🔸Smart Home Technologies 🔹Central AC/ Heat 🔸Luxurious waterfall shower head🚿 🔹Free street parking 🔥Message today to secure your reservation!🔥

Popular amenities for outdoor seating rentals in Shadyside

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Quick stats about holiday rentals with outdoor seating in Shadyside

  • Total holiday rentals

    Explore 90 holiday rentals in Shadyside

  • Nightly prices starting at

    Shadyside holiday rentals start at £38 per night before taxes and fees

  • Verified guest reviews

    Over 8,910 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    90 of Shadyside holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Shadyside rentals

  • 4.9 Average rating

    Shadyside stays are highly rated by guests – averaging 4.9 out of 5!