Smoking-friendly holiday rentals in Washington County

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! 


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.

City-Adjacent Wooded Retreat - Peace and Wildlife

1950’s Ranch on secluded road. No other spot has so much access to private forest, this close to the city! Take a stroll, build a fire or enjoy a sunset from the porch. Only :10 from hotspots like Shadyside and L-Ville. :15-:20 from UPMC Oakland. Full & twin beds. Sparse furniture, w/ cooking utensils included. This isn’t a hotel room, it’s a home in transition and we invite you to stay simply, easily & cheap! I live close by for help in town or for anything you might need during your stay.

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!

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!

The Cozy and Comfy Townhouse

Keep it simple at this peaceful and centrally-located place, surrounded by nature, only minutes to the stadiums and Pittsburgh main attractions. Enjoy a drink on the large covered porch, watch your kids play in the adjacent playground.. You will without a doubt enjoy how quiet our place is! It is the perfect place for your next visit to Pittsburgh. We wish you a warm welcome to the Steel City and can’t wait to hosting you!

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

Pet-Friendly Home with Fenced Yard

Discover your luxury Pittsburgh retreat! This modern 2-bed, 2.5-bath smart home comfortably sleeps 6. Occupying the top two floors, it features dedicated workspaces, a gourmet kitchen, and private outdoor areas with a BBQ. Perfectly located just a short trip from downtown, stadiums, and premier shopping. Ideal for families, remote workers, or city explorers seeking sophisticated comfort and convenience.

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.