Vacation rentals with outdoor seating in Shadyside, Pittsburgh

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Top-rated outdoor seating rentals in Shadyside, Pittsburgh

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Guest favorite

Guest suite in Pittsburgh

4.98 out of 5 average rating, 105 reviews

Lawrenceville Loft with Downtown Views and Garden

Bright and airy loft-style third floor apartment in an award-winning, recently renovated 1860s brick farmhouse with expansive urban garden, fresh produce and friendly hosts. Walking distance to the heart of Lawrenceville and several great local neighborhoods. Easy access to all of Pittsburgh with a peaceful setting to come home to. Upstairs loft shares the entrance with the house but has its own separate door to the suite/apartment. 1 good dog is ok please message me with pet details, no cats.

Jul 20 – 27

G$26,010 GYD per night

Guest favorite

Guest suite in Highland Park

4.97 out of 5 average rating, 142 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.

Aug 29 – Sep 3

G$18,020 GYD per night

Guest favorite

Apartment in Pittsburgh

4.84 out of 5 average rating, 111 reviews

Shadyside: Ultra Lux, 1 Bed/1 bath

Shadyside gem! Chic, stylish , spacious. Conveniently situated in the heart Pittsburgh's favorite neighborhood. Exceptionally comfortable layout includes an in-suite laundry & exclusive front porch! Eat-in or dine out at one of the many near-by restaurants. Fabulously located to quaint shops, unique restaurants, beautiful city parks, culture-rich museums, state-of-the-art sports facilities, Universities, Hospitals. Wonderful walkable location. Easy access to public transportation too!

Jun 13 – 20

G$35,258 GYD per night

Guest favorite

Guest suite in Pittsburgh

4.98 out of 5 average rating, 367 reviews

Lawrenceville Designer “Tiny Living”, Walkable

The Nesting Box is an ideal space to return to and recharge in after “free-ranging” locally. Comfortable, cool, and centrally located to the best of Butler Street. Designers collaborated to maximize the minimal space with creative comforts while experiencing "tiny living". Our shipping container addition led us to have 2 front doors. We welcome guests to our on-street guest suite. Urban family homestead with 2 cats, 2 dogs, and for 5 years 3 chickens that resided with us (recently rehomed).

Jun 9 – 14

G$22,534 GYD per night

Guest favorite

Home in Pittsburgh

4.98 out of 5 average rating, 180 reviews

PBR - Pittsburgh Bloomfield Rowhouse

A fully renovated, charming, and comfortable home in the heart of Pittsburgh's Little Italy. Location is just steps away from great dining, shopping, and entertainment. Historic Bloomfield is centrally located in the city and only minutes from local universities, hospitals, and stadiums. This pet friendly 3 bedroom house is perfect for families, friends, and business travelers. Whether you are visiting for work or leisure, this house will make your stay even more delightful. We welcome all!

Oct 26 – Nov 2

G$35,665 GYD per night

Guest favorite

Apartment in Shadyside

4.95 out of 5 average rating, 221 reviews

Bohemian Place Shadyside Style

Designed for longer stays. Sanitized for each guest, 2 bdm apt with private entrance to the 3rd floor apartment. Steps from shops, grocery, restaurants, public transportation. *Private ent., extra twin foam bed. *Kit incl, plates, toaster oven, microwave, stove, H2O kettle, French Press * 1 block RESTAURANTS Walnut St./ Ellsworth Ave / Museums *HV/AC *5 min. walk grocery. *UPMC Shadyside, Pitt, CMU, Chatham Univ. Bike rent - 1/2 blk. bike route *2 min. walk to busway to downtown.

Dec 19 – 26

G$19,398 GYD per night

Guest favorite

Home in Pittsburgh

4.98 out of 5 average rating, 142 reviews

Perfect Location in Lawrenceville: Top 10 airbnb

Named Top Ten Trendiest AirBnB's in Pgh Dec. 2021 by Living Pittsburgh! Beautifully renovated three story brick row house built in 1890 - perfect location a few hundred feet from Butler Street in Lawrenceville. Gorgeous street - very safe area. 2 miles from downtown Pgh. Street parking. Entry keypad. Private outdoor area with seating. French bakery, tons of restaurants & shops right out the front door. You couldn't find a better location in L-ville - our favorite neighborhood in PGH!

Jul 11 – 18

G$40,629 GYD per night

Guest favorite

Apartment in Pittsburgh

4.95 out of 5 average rating, 391 reviews

Charming cozy apartment with deck.

This little jewel of an apartment is charming and cozy, with private entrance, 1 bedroom, small sitting area, fully-equipped kitchen, bath, laundry access, wifi and private deck. We are on a quiet shady street near 644-acre park. 2.5 miles to universities, 1 mile to Bakery Square. NO CLEANING FEE, so a better value than other listings! Comfortable queen-sized bed with memory foam mattress topper. Many nice amenities and original artwork. Small but homey with lots of little luxuries!

Sep 3 – 10

G$19,710 GYD per night

Guest favorite

Apartment in Pittsburgh

4.98 out of 5 average rating, 109 reviews

Cute Apt Minutes from Downtown and Stadiums!!

This apartment is located in Millvale, walking distance to many great breweries, shops and restaurants. It is right over the bridge from the popular area of Lawrenceville and a 5-minute drive to Downtown and the North shore to the stadiums. This apartment is out of the hustle and bustle of the city, yet central to all of the great places Pittsburgh has to offer. While staying here you will feel right at home! Be sure to check out our guidebook for more information about this property!

Jan 1 – 8

G$22,338 GYD per night

Guest favorite

Home in Pittsburgh

4.92 out of 5 average rating, 184 reviews

Cozy studio apartment, private entrance + porch

This cozy, private basement apartment is located on the tippy top of Pittsburgh's North Side in a neighborhood called Spring Hill. Hello incredible view! By car, you'll be minutes from downtown, the stadiums, incredible restaurants, concert venues, art museums and more! Enjoy your own entrance, porch, full bath, working area & kitchenette. Two sweet cats & one very cool kid live on the premises. We don't allow the cats in the room but you may find them lounging on the back porch.

Sep 28 – Oct 5

G$15,646 GYD per night

Guest favorite

Home in Pittsburgh

4.91 out of 5 average rating, 348 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).

Oct 3 – 10

G$25,884 GYD per night

Superhost

Apartment in Shadyside

4.85 out of 5 average rating, 216 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!🔥

Jan 19 – 26

G$20,767 GYD per night