Smoking-friendly holiday rentals in Youghiogheny River

House 3bed Free Parking Walk to Bars & Shops

Have fun with the whole family & friends at our beautiful modern house. Located on a quiet street at one of the most vibrant neighborhoods in Pittsburgh South Side.Walking distance to bars & restaurants, grocery stores and coffee shops. Private fenced backyard perfect for families with kids. Free street parking available for our guests. Carnegie Mellon university, Pitt university, PNC Park and Heinz field 3 miles away from house. 3 bedrooms - king, queen and twin size beds, closets & bathrooms.

The Dave Cave

This unique 2 bedroom unit is an ideal place for cigar smokers and music lovers. The spacious apartment is decorated with a rock n' roll theme reflecting it's reputation as a popular live music venue (shows once every 2 weeks in the summer months). To access the 2nd bedroom you must go thru the master bedroom, so it's more of a bonus room for groups comfortable sharing spaces. Its located above the famous Leaning House Fine Cigars, established in 2006. We require a profile picture of your face.

Hot tub | BBQ | Fire pit | Garage | Near Downtown

Minutes from Pittsburgh’s best: -3 min to Strip District -6 min to CMU & Pitt -7 min to Lawrenceville -9 min to Downtown (PPG Arena) -12 min to Northside (PNC Park) Unwind with these amenities: ✓ BBQ grill + hibachi setup ✓ Backyard fire pit for marshmallow roasting ✓ Bug-free outdoor dining tent ✓ Indoor jetted whirlpool hot tub for 2 ✓ Private bathroom — no sharing unless it’s your partner ✓ One-car parking garage, plenty other street parking Perfect if you want city access and privacy.

PRT to WVU! Massive Patio, Hot Tub & Bar!

Welcome to the ultimate Mountaineer Basecamp! Hosted by a local Ice family member and professional GC, this premium townhouse is built for comfort and convenience. 📍 LOCATION & TRANSIT: Walk across the street to the Mountain Line terminal! Buses run every few minutes to downtown and the PRT. 4 direct lines go to Ruby Memorial Hospital—perfect for nurses or crews at the new Cancer Center. 🏆 AMENITIES: Enjoy our massive covered patio, private bar, and hot tub. 50% monthly discount available!

Dreamy Cottage: 2 bed w/fireplace, tons of charm

This family/pet friendly 2 bed/1.5 bath Dreamy Cottage, located in a lovely, quiet, family neighborhood in the center of Westmont is recently renovated and designer decorated in a boho-vintage-world-chic style. Step in become transported into a world of warmth, charm and comfort. You will find no other accommodation in the area with such extreme detail to design and comfort as this unique designer-owned home. There is a 25lb pet limit, 1 pet per visit acceptance at discretion of owner.

4 Story Home|Triple King|Backyard|UPMC Shadyside

Welcome to our stunning 4-story home in Shadyside! This home is huge with 4 BRs + a finished basement along with 3.5 baths, perfectly located right next to UPMC Shadyside Hospital. Also a short walk from Giant Eagle Market District! ⭐7 beds with memory foam mattresses (3 King / 1 Queen/ 3 Full) ⭐Private backyard ⭐1 rollaway bed + 1 crib + 2 sleeper sofas ⭐Washer/ dryer ⭐Street parking (Paid options nearby) My team and I are here for you 24/7 before, during and after your stay with us!

Creekside Inn, Ranch w/xtra gameroom trundle beds

Sleeps 10! King in Bed 1 (+ crib & rocker), Full & Double in Bed 2, 2 twins in basement game room, plus a couch for additional guests. 2 full bathrooms, one on each floor. Level parking & step-free main entrance — handicap chair & grab bar available. Fast WiFi throughout. Secluded backyard oasis with fire pit, creek, grill & patio — yet right off the main road. Fenced & pet friendly. Pool table, PS3, TVs, kitchenette/wet bar, office & printer. Full infant & toddler gear included.

Valley View Sunrise Site @TheGreat48Escape

Seeking peace, privacy and nature? The Sunrise Site delivery! This is a BYO tent campsite. This lovely slice of Laurel Highland heaven offers breath-giving views over Quecreek Valley. A mowed mile-plus trail provides a great place for a morning walk or an evening stroll through seasonal wildflowers. Great sunrises & stargazing . Gas, shops, eateries, Flight 93, Ligonier, Fallingwater, state parks, wineries, breweries, elephants! swimming holes, whitewater rafting nearby.

Larkins Way Urban Oasis

Modern, bright South Side oasis just steps from Carson St. Sleeps 8 in 2 spacious bedrooms with en suite baths plus a comfy U-shaped sofa that can sleep two (one on each arm). Enjoy vaulted ceilings with skylights, 2.5 baths, and a fully equipped kitchen. The guest bedroom includes a desk and chair for remote work. Relax on the large private deck with grill, firepit, string lights, and plenty of seating under a peach tree. Driveway parking for one and pets welcome!

Modern 3BR Townhouse Close To Downtown Pittsburgh

Welcome to this stylish 3-bedroom townhouse just minutes from downtown Pittsburgh. Comfortably sleeping 6, the home features a bright, modern living room, cozy bedrooms, and a fully equipped space for relaxing or entertaining. Step outside to a charming private deck with seating and string lights, perfect for evenings. Conveniently located near Pittsburgh’s major stadiums, it’s perfect for game days, families, or business travelers seeking comfort and convenience.

Nanny’s Rustic Retreat: Daisy Hide-A-Way

Nanny’s Rustic Retreat is a private, adults-only nature sanctuary designed for relaxation and freedom. Guests who appreciate a body-positive environment and natural outdoor living will feel at home. Discretion and respect are required.” Provided: 2 pillows, blanket and mattress cover & sheets/pillow cases for the full size bed in the cabin. There are two high chairs on the porch. All guests can enjoy the naturalist environment : hot tub/swimming pool area.

Magnolia River

Wake up ON THE RIVER to river front view to reset and rejuvenate on the Youghiogheny River. This thoughtfully designed home is equipped for all your needs and has Riverfront access. No place captures the charm and homey nature quite like Magnolia River. There are refurbished pieces that keeps the spirit of Friendsville going. This quaint house is not just for nature lovers; a family-friendly atmosphere lives here too.