Holiday rentals with outdoor seating in Downtown Pittsburgh

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.

Grandview Ave Luxe - Sweeping City Views & More!

Walk in and say wow! Stay on Grandview Ave., the street with million dollar views of Pittsburgh. Our completely remodeled penthouse features the luxe touches you'd expect - Breville espresso machine, wine fridge, wet bar, smart home features, bidet, rain shower, & more! Specifically designed for a couple that wants the nicest accommodations in the city, but comfortably sleeps 4 in 2 king beds. Park in our private lot, then walk 2 blocks to Shiloh St for bars & restaurants. Prepare to be amazed!

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!

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).

Amazing views! Free Parking!

After a year-long restoration project, we are thrilled to present our home in Pittsburgh's historic north side. What awaits you is a quiet, downtown gem surrounded by nature with amazing city views. What You'll Love: -Total and complete renovation between 2020-2021 -Gourmet, fully-equipped kitchen including coffee/tea station -Remarkable city views -Close to stadiums, downtown, museums -Relaxing patio -Gigabit internet connection -Peaceful nature surroundings -Comfortable memory foam beds

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).

Spacious Studio w/ Million Dollar City Views

Enjoy a million-dollar view in our cozy studio apartment located on a quiet cul-de-sac with free off-street parking! Just minutes from E Carson Street in the South Side, you'll be close to shopping, dining, and nightlife. Downtown, stadiums, universities, cultural arts venues, and hospitals are all less than 10 minutes away. Plus, with easy access to I-376, you're a short drive to Monroeville or Robinson in about 20 minutes! Perfect for both work and play.

Old Millionaire's Row Suite |Prime Location |Heinz

There is no real way to describe the detail and architecture of this place. It was carriage home by millionaire’s row in the 1900s and is still a historic building in PGH. The architecture is truly amazing, not to mention the convenience today! You can walk to all the stadiums, casino, and countless bars, restaurants, and breweries! The T takes your right downtown for FREE and is less than a half mile walk. This unit is Dog-friendly for an additional charge.