Smoking friendly holiday rentals in Allegheny County

4.64 out of 5 average rating, 104 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!

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

Guest favourite

5 out of 5 average rating, 11 reviews

Spacious 2br Pet Friendly Wi-Fi

Bring the whole family to this great place with lots of room for fun. It is a great location with quick access to Parkway. It is close to several malls, restaurants, bars and convenience stores. Peaceful Mornings and fun-filled afternoons await you at this unique experience! The unique Property combines all the best that the Southside of Pittsburgh has to offer. Ambient rooms with led lights, and Murals to Boost your getaway. Full Kitchen, Quartz countertops, spa shower, 55 inch Flat Tv!!!!!!!!

4.83 out of 5 average rating, 48 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.

Guest favourite

4.88 out of 5 average rating, 105 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.

Top guest favourite

4.96 out of 5 average rating, 418 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.

4.92 out of 5 average rating, 12 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, 6 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.