Holiday rentals with outdoor seating in Shadyside

Modern & Upscale King Bed Suite|Private w/Parking!

Enjoy our spacious & upscale 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 ⭐In-unit washer/ dryer ⭐Large standing desk w/ speedy wifi & extra monitor ⭐Pet friendly ⭐24/7 Guest support ⭐Free off-street parking ⭐Close to CMU/ Pitt! ⭐$0 cleaning fee!

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.

HOT TUB KING bed Luxurious 2 bed in PRIME location

Enjoy a stylish experience at this centrally-located getaway. I believe in maximum comfort. All the comforts and amenities of home and more; including memory foam beds, smart tv, nespresso machine, and more. *5 miles from Heinz Field *20 minute walk to Lawrenceville strip *10 minute walk to Children's Hospital *1 mile from Shadyside *5 minute walk to West Penn Hospital This is the ultimate spot for a couples retreat or extended stay... NO PARTIES ALLOWED:) Please note the open stair case!

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!

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).

The Bellevue Suite *Free parking 10mins to dwntwn

*PLENTY OF FREE STREET PARKING* 1 BDRM apt in the up and coming town of Bellevue, just a 10 min drive to downtown and the stadiums. This is a 3rd floor unit in my 100+ year old four-square home. It has a private entrance with a Keypad for Airbnb guests, there are 2 other units in the building. Its in walking distance to public transit, shops, restaurants, places of worship, banks, and a grocery store. Pet friendly ($50 fee) just add your pet under pets in the guest section when booking.

Urban serenity, privacy in charming carriage house

Carriage house apartment all to yourself. Sleeps 3. Uniquely charming. Private, quiet, and self-contained. Keypad check-in, free parking, laundry, many amenities. Responsive hosts on site. Great location in lively East End. Convenient to hospitals, restaurants, shopping, entertainment, public transportation. Ideal weekend getaway for couples. Perfect for traveling workers. Extended stay discounts for bookings of a week or more. Discounts offered for return guests; please inquire.

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

Betwn Walnut & Ellsworth! Sleeps4! Parking&Laundry

LOCATION! LOCATION! This apartment is approx 200 feet to Ellsworth Avenue and approx 700 feet to Walnut Street! My apartment features a deck, open-concept layout, central air, and free laundry. One parking spot is available for free, if reserved in advance. Please see the parking policy below. The apartment sleeps 4 people. The bedroom has a queen bed. The living room has a sofa that conveniently folds down into a queen-sized bed.