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! 


#640 Central Apt Butler St Lawrenceville Pets F.

Hello I’m Gus I'm a Colombian that's been living in Pittsburgh for seven years now and has fallen in love with the city. I've started a new life here, but I know what it’s like to be away from home. I'm a very friendly person, love to meet new people and share experiences, I started this business trying to create a “home away from home” environment for travelers. The space is modest but inviting and I'll be happy to host you and do my best to provide you with a pleasant stay in my home. 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.

1880ft | 85”TV | Fenced Yard | WD | Pets OK | FIOS

Luxury Pittsburgh, PA Entire Home. Close to Stadiums, Downtown & Shopping ~AMENITIES~ ✓ Keyless Smart Lock Access ✓ Security: 3 Exterior Cameras ✓ 3 Bedroom Home w 3 Private Baths Per Bedroom ✓ 1 Powder Bathroom (Kitchen/LR) ✓ Sleeps 6-8 ✓ 2 King Beds, 1 Queen, 1 Oversized Lux Sofa ✓ High Speed FIOS w 3 Workspace Desks ✓ Smart TV’s: 85", 65", 65”, 50"+ SmartHub ✓ LEED Certified Smart Home w HE-HVAC Control ✓ Covered Front Porch ✓ Fully Fenced Backyard + Patio Area ✓ Gas Weber BBQ Grill

Head to Pittsburgh From Mt. Lebanon Cottage

Mt. Lebanon Cottage is a craftsman-style home that fuses contemporary styles with traditional elements. Enjoy our well-equipped kitchen, enjoy a coffee for two on the deck nestled in the trees or unwind on the front porch and enjoy the friendly neighborhood vibe. The home is in a walkable neighborhood of tree-lined streets and friendly locals. Blocks from unique shopping boutique options and dine at tasty local restaurants. Hike in the nearby nature and visit Pittsburgh just minutes away.

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!

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!

Modern, Near Downtown and Strip, BBQ, Jetted Tub

Do you want to be: -3 min to Strip District -6 min to CMU/Pitt -7 min to Lawrenceville -9 min to Downtown -12 min to Northside -13 min to Squirrel Hill Do you also want to: -Grill BBQ or try your hibachi skills -Roast marshmallows in your backyard -Dine inside a bug-free backyard tent -Relax in the indoor jetted whirlpool hot tub for 2 -Have your private bathroom — no sharing unless it’s with your partner? -Have a one-car parking garage Look no further!

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.