Smoking friendly holiday rentals in Allegheny County

4.59 out of 5 average rating, 108 reviews

#420 Tiny Studio Bath/Kitchen Carson St.

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!

Superhost

4.7 out of 5 average rating, 27 reviews

Private unassuming home with lots of extras!

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

Superhost

4.83 out of 5 average rating, 53 reviews

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.

4.88 out of 5 average rating, 107 reviews

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.

4.96 out of 5 average rating, 425 reviews

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.

Superhost

4.85 out of 5 average rating, 20 reviews

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!

Top guest favourite

Home in White Oak

5 out of 5 average rating, 7 reviews

Creekside Inn & Backyard Camp

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.

4.91 out of 5 average rating, 368 reviews

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.

Top guest favourite

Townhouse in Pittsburgh

4.95 out of 5 average rating, 128 reviews

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!

4.91 out of 5 average rating, 11 reviews

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!

4.67 out of 5 average rating, 3 reviews

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.