
House vacation rentals in Shadyside
Find and book unique houses on Airbnb
Quick stats about house rentals in Shadyside

Total vacation rentals
Explore 150 vacation rentals in Shadyside

Nightly prices starting at
Shadyside vacation rentals start at G$6,267 GYD per night before taxes and fees

Verified guest reviews
Over 6,670 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
140 of Shadyside vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Shadyside rentals

4.8 Average rating
Shadyside stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated house rentals in Shadyside
Guests agree: these houses are highly rated for location, cleanliness, and more.

Stunning 4-story Home | Sauna | Parking | Walkable
Welcome to our stunning & secluded 4-story home! This home is huge w/ 4 BRs and 2.5 baths, perfectly located in the heart of Shadyside. Short walk of plenty of restaurants, coffee shops, bars, shops, and steps away from Giant Eagle Market District! ⭐4 beds with memory foam mattresses (2 King / 2 Queen) ⭐Sauna ⭐2 private decks ⭐Futon + air mattress + 1 rollaway bed + 1 crib ⭐Washer/ dryer ⭐Off-street parking(3 cars) My team and I are here for you 24/7 before, during and after your stay with us!

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!

2 beds/1.5 bath Hygge-Hus, Minute to Cafes & Shops
Enjoy a beautifully designed retreat in this former Candy Shop in the heart of Pgh's Lawrenceville neighborhood. The open floor plan includes two floors with a bed on each floor (think 'loft' instead of closed rooms with doors). The kitchen opens to a Tolkienesque garden patio to be at peace. Lawrenceville's restaurants, shops, theaters, and cafes are just a minute's walk from your front door. Rest, relax, sleep in, cook, eat in, and recharge in a quiet, environmentally conscious cozy home.

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.

Upscale Modern 2 BR Apartment
This spacious, newly renovated, fully equipped and private access apartment was built for your enjoyment! The granite counter tops and porcelain tiled shower are a hint of the luxuries throughout. You can park on the property or on the street. Located in the heart of Squirrel Hill, right near Schenley park, the Squirrel Hill business district and bus lines. Easy Access to Bakery Square, Shadyside, Waterfront, Downtown, Museums & Galleries, Universities, hospitals, and all Sports venues.

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.

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.

Cheerful 3-bedroom home with on-street parking
Enjoy your stay in this beautifully renovated 3 story 1920s centrally-located home in the Greenfield neighborhood of Pittsburgh (right next to Squirrel Hill). Less than 10 minutes to Downtown, PPG Arena, Bakery Square, CMU, Pitt, Chatham, and Duquesne University. Minutes away from excellent restaurants and bars in Pittsburgh. Fully equipped entire home for an extended or few nights stay. Enjoy outdoor seating on the front porch and back deck with a fenced in backyard.

Fire Pit + Family Friendly + Great Location!
Welcome to our family-friendly home in Bloomfield! Tickle the ivories on our baby brand piano while you send the kids upstairs to play with coloring books, toys, and more. Cook a great meal in our well stocked kitchen, or relax on the couch and watch Netflix. At night, spark up the fireplace and enjoy an evening outside with friends! If you're an "out and about" type - you're just a few blocks from the main drag in Bloomfield, full of great bars & restaurants!

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)

Off Street Parking, Walk to Hospitals + Great Food
Our completely refreshed apartment in Bloomfield invites you to unwind in a relaxing oasis. Located conveniently close to the many great restaurants and bars in the area, our comfortable home away from home features a large bathroom, fully equipped kitchen with laundry & wine fridge, off-street parking, and more. With three full bedrooms, multiple work-from-home desks, make this your home away from home, perfect for short or long stays!
Popular amenities for Shadyside house rentals
House rentals with a pool

Renovated Cozy Duplex w/pool, Close to downtown

Urban Pittsburgh Home w/ Pool

Rooftop Deck | Perfect for Entertaining | Upscale!

Heated Pool Oasis • Free Parking • 5 min to PGH

The Burgh Beach House

Cozy Home in Pgh area Pool OPEN, Sleeps up to 10

A beautiful cozy home away from home!

Charming Pittsburgh Getaway - Private Home- 2 Beds
Weekly house rentals

Luxury Mountainside with Spectacular Views

Childrens Hospital Nearby | Park Free | Colorful

2 Outdoor Patios ★Parking ★Kid Friendly ★Beautiful

PBR - Pittsburgh Bloomfield Rowhouse

Skyline Haven:5BR/3.5BA +2 parking spots + Rooftop

Block from Butler St. Exposed Brick Beauty!

Urban converted gas station in heart of South Side

Dual Rooftop Decks with Skyline Views & Firepit
Private house rentals

Brand New! Luxury 5 Bed Home in Shadyside~Parking!

Quiet Cul-de-sac | Hot tub | Backyard | EV+Garage

Modern 4BR Home | 2 King Beds & Private Backyard

Dedicated Parking | 2 King Beds | Arcade | BBQ

Upscale 3BR | Prime Location + Off-Street Parking!

Prime Butler St | Outdoor Lounge | Family Friendly

Spacious East End Escape w/ Spa Bath & Game Loft

East End Pittsburgh 4 Bedroom Getaway
Destinations to explore
- PNC Park
- Acrisure Stadium
- Fallingwater
- Seven Springs Mountain Resort
- Carnegie Mellon University
- University Of Pittsburgh
- David Lawrence Convention Center
- Ohiopyle State Park
- Sri Venkateswara Temple
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- Raccoon Creek State Park
- Moraine State Park
- Point State Park
- Petersen Events Center
- Phipps Conservatory and Botanical Gardens
- Schenley Park
- Kennywood
- Carnegie Science Center
- National Aviary
- PPG Paints Arena
- Laurel Hill State Park
- McConnells Mill State Park
- Children's Museum of Pittsburgh





