Smoking-friendly holiday 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! 


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.

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.

2/2.5| 1200ft| Fenced| FIOS| 85”TV| Pets| Grill

Luxury Pittsburgh, PA Home with a separately rented apartment on the first floor. Close to Stadiums, Downtown & Shopping ✓ Keyless Smart Lock ✓ Security: 3 Exterior Cameras ✓ 2 Bedroom Home w Private Bath Per Bedroom ✓ 1 Powder Bathroom (Kitchen/LR) ✓ Sleeps 4-6 ✓ 1 King Bed, 1 Queen, 1 Oversized Lux Sofa ✓ High Speed FIOS w 2 Workspace Desks ✓ Smart TV’s + SmartHub ✓ LEED Certified Smart Home w HE-HVAC Control ✓ Covered Front Porch ✓ Fenced Backyard + Patio Area ✓ Gas Weber BBQ Grill

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 & Backyard Camp Sleeps 10

Ranch home with everything necessary on main floor. A restaurant/bar within walking distance in front and a camping experience in the backyard with a huge firepit, so bring a tent! The lower level has a game room with a pool table, PS3 game system, TV, a kitchenette w/mini fridge/microwave, 2nd bathroom and a small workspace. There is parking for 6 cars. No stairs to access main floor. This is a rare blend of seclusion and access to everything else just steps or a minutes' drive away.

420 friendly premium apt w jet tub, air fryer oven

We’d love to host you at our 420 friendly two bedroom apartment. The unit has a custom shower/ jet tub combo, and modern kitchen. There is a potential noise (although not enough noise to bother most guest) This completely private apartment is located on the first floor of a three level building. There is another Airbnb above this unit, and an owners area below this unit. Also, the apartment is located on a Main Street, If you are a light sleeper this may not be the unit for you.

Mt Washington Townhouse (A Grand View)

Enjoy the phenomenal view from the Living room, Deck & Master Bedroom! Stroll down the block to enjoy some of Mt Washington's best restaurants & overlooks. Take the Duquesne Incline down the hill to enjoy a short walk to the North Shore (Heinz Field, PNC Park or Stage A&E) or ride one of the Gateway Clipper boats to your destination. An inexpensive Uber ride gets you back to Mt Washington to enjoy a nightcap with one of the greatest views Pittsburgh has to offer!

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!

Family & Friendly Stay in Pittsburgh, PA.

This cozy home is the perfect balance of comfort and convenience. Located in Eastmont, a quiet neighborhood. You're just minutes from all the shops, restaurants, and essentials in Pittsburgh and Monroeville, making it ideal for families, couples, or professionals needing a functional, well-located stay. Inside, you’ll find a warm, thoughtfully designed space with modern amenities, rustic touches, and everything needed to feel at home.

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.