House holiday rentals in Shadyside

Urban Oasis Home - Hot Tub, Pet-friendly, Koi Pond

This charming historical home is close to everything! You can be downtown within 5 minutes. You'll be minutes from the stadiums, museums, and the casino! Pamper yourself. Relax in the hot tub while listening to the sounds of the waterfall over the pond. Watch the colorful Koi splash and play. The meticulously landscaped grounds have countless surprises and beauty in every season. You will enjoy every comfort in this luxurious three-bedroom and 2.5 baths. There's even a shower for your furbaby!

Off-Street Parking, Steps to Butler St., Patio!

In the heart of lower Lawrenceville, our place exudes historic Pittsburgh charm while providing an incredibly cozy experience. Our spacious kitchen invites you to cook a great dinner. Our comfortable living room surrounded by historic brickwork + open staircase encourages you to relax and watch Netflix. The patio welcomes you with fresh air. With two full bathrooms, two couples or a family can get ready for the day (or night!) Within walking distance, bars, breweries, and restaurants abound!

Avant-Garde Escape by Walnut

Welcome to our stylish, newly-renovated home, complete with modern amenities, tasteful decor, and all-new everything. Perfectly located just steps from Walnut Street’s best restaurants, bars, and shops—a prime base for exploring Pittsburgh! ⭐ 2 King beds + 2 Queen beds + 5 rollaway beds or futons - can sleep 16 easily! ⭐ Private deck ⭐ Free Washer/Dryer ⭐ 2 Off-Street Parking spaces (Free) ⭐ Pack N Play & High Chair Our team is here 24/7 to support you before, during, and after your stay!

Near Hospitals + Great Food, w/ Off-Street Parking

Simple, comfortable, and steps from some of Pittsburgh’s best food—this 1BR/1BA Bloomfield apartment puts you in the heart of it all. A short walk to Apteka, Tessaro’s, Fet Fisk, West Penn Hospital, and more. Enjoy free off-street parking (hard to find here!), fast Wi-Fi, a well stocked kitchen, and a remote work setup. Whether you're grabbing dinner down the block or catching up on a show with local coffee in hand, this space offers unbeatable value in one of the city’s most walkable spots.

Sunny, Creative Duplex in Friendship

You and your travel companions will be in an ideal Pgh spot when you stay at this Friendship neighborhood home. With 3 floors, you'll have lots of room to spread out or gather together. This beautifully updated 100-year-old home is a creative space, filled with art from Pgh artists, cheery textiles from around the world, and vintage decor scattered throughout. It’s a charming retreat for artists & writers, a cozy spot for families, or the perfect place for larger groups to share a getaway.

Block from Butler St. Exposed Brick Beauty!

Only a block to Butler St., one of the most walkable areas of Pittsburgh! This to-the studs renovated property went live in early 2022, sitting on a quiet alley in Lawrenceville. Featuring a well appointed kitchen, beautiful bathroom, spacious living areas, and exposed brick everywhere, this is a place you want to call home for a few days to a few months! Curl into the couch and watch Netflix, or if duty calls, work from home at the desk with high speed 300mbps internet. Book today!

3 BR home|Steps from Walnut Street w/Free parking!

3 Bed / 2 Bath home in the heart of Shadyside! This home is located steps away from popular Walnut Street, which has plenty of fun restaurants, shops and more! 💫Four memory foam beds (2 king/ 2 queen) 🌟King bed w/ Full bathroom on First Floor (No Stairs) 💫Twin-sized rollaway bed + Pack n Play Crib 💫Off street parking 💫Private front and back patio 💫Free in-unit washer/ dryer 💫Fully stocked kitchen My team and I are here for you 24/7 before, during and after your stay with us!

Highly rated, 2bd/1.5 bath home/backyard/parking

Welcome to La Casita Millvale, a newly renovated 2 br/1.5 bath (sleeps 6) home in the heart of trendy Millvale/Lawrenceville and close to all Pittsburgh has to offer. Enjoy our expertly designed space including fully equipped kitchen with quartz countertops and stainless steel appliances, well-apportioned rooms with luxurious queen mattresses, and a third floor entertainment room and work space. Sip your morning coffee on the front or back porch and relax in the private backyard.

Childrens Hospital Nearby | Park Free | Colorful

✨ Modern Comfort Meets Pittsburgh Charm ✨ Step into this stylish 2BR/1BA three-story row home a short walk to Children's Hospital! Set up for both long & short stays, cook in a fully stocked kitchen, work from the cozy desk, or unwind with locally roasted Commonplace coffee & a 60" 4K Smart TV. With eco-friendly touches, free parking, and proximity top breweries, top eateries, and more, our colorful Pittsburgh home is your perfect base to explore Pittsburgh.

PRIVATE MINI STUDIO (D2)

This Mini Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, sleeper sofa, a kitchenette and a full bathroom with a private entrance on the 3rd floor of a beautiful 1890s Pittsburgh mansion. It's the size of a large room and works very well with guests that are planning to work, or go out enjoying the city and come back to a safe, clean and comfy place to recharge for the night (not suitable for kids under 10).

Cozy home in "Little Italy"

Weekly 20% disc $924- 7 days Monthly 35% disc $3260 Nice spacious home on quiet street in Pittsburgh's "little Italy".(Bloomfield) Two blocks from Children's Hospital. One two and five minutes from three bus lines to downtown Pittsburgh. 8 minutes to 31st Street Studios. (Same bus lines) Walk to many fine restaurants on Liberty Ave. Off street parking.( 2 vehicles) One block from historic Allegheny cemetery. (2nd biggest cemetery in US)

Luxe 5B/2.5B: Family-Friendly + Off St. Parking

Experience Pittsburgh from our beautifully renovated 5BR/2.5BA historic home, just one block from Shadyside's vibrant Walnut Street. Perfect for 10 guests, this 2800 sq ft space features a chef's kitchen, dedicated workspace, and private parking. Enjoy modern luxury with family-friendly amenities in a prime, walkable location. Ideal for families, groups, and remote work getaways.