Smoking friendly vacation rentals in Pittsburgh

Unique Artsy 2 Bdrm Apt 1.5 mi from Downtown

Whether you’re coming for a sports game, a concert, a college graduation or just sightseeing- this place offers you a perfect location. 
Just 1 to 2 miles away from some of the Pittsburgh’s most interesting venues, approximately 300 yds from the bus stops and half a block away from Interstate I-279 and PA Rt.28. This cozy, freshly remodeled apt located in a 123 y.o. bldg in historic Deutschtown neighborhood offers great city views, a taste of history & the latest modern conveniences. Welcome! 


Private house in Ross Twp 15 mins to north shore!

Unassuming private home on cul-de-sac in the woods. 2 bedrooms with double beds to sleep 4, but with rollaway and sofa bed can accommodate 7. Finished basement with comfy seating, poker table, TV, etc. leads to back patio and fenced in yard. Dog door in basement! Fully equipped office with monitor, printer scanner. Fully equipped gourmet kitchen. 15 minutes to downtown! 10 minutes to Ross park mall. Wonderful quiet neighborhood. Perfect for families with kids/dogs or a romantic getaways

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.

10 min Walk to Draft | Historic North Side 4BR

Park your car and leave it. 10-minute walk to the Draft stage/North Shore. Perfect for groups/media teams. Secure the last massive 4BR historic home walking distance to the Draft! Forget paying $800+ for a tiny casino room—bring your group to this 3,000sqft luxury retreat. 🔥 VIP Perks: • 3 FREE Parking Spots: A true North Shore unicorn! • Walk Everywhere: 15-min walk to the stage & stadium. • Sleeps 7+: 4 Bedrooms / 5 Beds / 3.5 Baths. • Dog-Friendly: Front & back patios! Book with confidence!

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.

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.

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!

cozy & modern house (loft style)

Welcome to my cozy world 🤗 Hope you will enjoyed while keeping the place as it is 🫣 There are 2 bedrooms: 1. The first bedroom is upstair with a master Bathroom and a dressing room. (Queen size) 2. The second bedroom is in the remodeled basement. (Full for 2 persons) Neighborhood Perks • Great restaurants are just a short walk away. • Church Brew Works is 3–5 minutes on foot. • Downtown is only a 10-minute drive.

Stylish 2 BD on Southside

Relax and unwind in this comfortable and spacious 2 BD apt in the heart of the south side of Pittsburgh while being 10 mins from Downtown Pittsburgh! The city offers award-winning restaurants, Boutique shops, and a Lively nightlife. When ready, enjoy the stylish apt and the many amenities it comes with: Free Parking, High Speed Wi-fi, Smart TV, Fully Equipped Kitchen, Office Desk, Cozy Bedroom w/ Queen Bed

Cozy Carnegie Cottage close to Pittsburgh

Get a real feel of the rolling hills of Pittsburgh while staying in a comfortable cottage built on a hill in a peaceful wooded setting. Plenty of room to relax and unwind while enjoying nature. The cottage is only 10 minutes from downtown Pittsburgh (park and ride and bus is within walking distance) and the Pittsburgh Int'l airport is only 15 minutes away. Local park is also within walking distance.

Pet-Friendly Home with Fenced Yard

Escape to a luxury 2-bed, 2.5-bath pet-friendly smart home in Pittsburgh for up to 6 guests. This private two-floor retreat features en-suite bathrooms, a gourmet kitchen, dedicated workspaces, and a fenced backyard with a BBQ. Perfect for families or remote workers seeking modern comfort just a short trip from downtown.