Family-friendly holiday rentals in South Side Flats, Pittsburgh

Find and book unique family-friendly homes on Airbnb

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Popular amenities for South Side Flats, Pittsburgh family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Guest suite in Highland Park
4.85 out of 5 average rating, 227 reviews

Entire private floor (giant Jacuzzi with shower!)

ChristopherRating, 5 stars3 weeks ago
Very pleasant and helpful host. Very clean unit
Guest favourite
Home in Squirrel Hill North
4.87 out of 5 average rating, 104 reviews

Hot Tub Infrared Sauna Peloton treadmills

AmyRating, 5 stars1 week ago
Andi’s place worked out perfectly for our sisters weekend. For 5 people everyone could have their own bedroom and there was enough sitting space for us all. Plenty to do with restaurants, museums and parks within walking distance or a short drive, then once home the house was quiet. Recommend!
Top Guest favourite
Home in Shadyside
5 out of 5 average rating, 20 reviews

Luxe Shadyside Spa + Parking + 6 Beds + Zen Garden

MarlaRating, 5 stars5 months ago
Oh my goodness! Rick is so thoughtful! And super communicative! He provided incredibly detailed information about how to access the house and the parking. Additionally, he had so many thoughtful details in the house in the way of snacks and beautiful flowers. And while we didn’t take advantage of the extensive list of restaurants because of being in town for the holidays, it was really nice how much information he provided. It was a great location especially to our family in Squirrel Hill.
Guest favourite
Home in Squirrel Hill North
4.92 out of 5 average rating, 173 reviews

hot tub fire pit Art & Wellness Retreat

AlanRating, 5 stars2 weeks ago
We enjoyed staying at Andi‘s place very much. Andi was very responsive and very proactive. If we had a question an issue whatever she took care of it right away. I would stay at Andy‘s place again if need be. Andi was great and went above and beyond
Top Guest favourite
Bungalow in Oakmont
4.99 out of 5 average rating, 74 reviews

Oakmont Home with Hot Tub

KevinRating, 5 stars2 months ago
Always a joy to stay here (which we try to do every time we come to town). The house is comfortable, well-furnished, and always spotlessly clean. And it’s a real home, not a soulless, cookie-cutter Airbnb rental. Plus, Laura is a delightful host, super friendly and very responsive. Don’t hesitate.
Superhost
Home in Squirrel Hill North
New place to stay

*infrared sauna *hot tub* US OPEN NFL draft

Family- and pet-friendly home rentals

Superhost
Home in South Side Flats
4.86 out of 5 average rating, 43 reviews

House 3bed Free Parking Walk to Bars & Shops

KatherineRating, 5 stars1 month ago
Ryan was very responsive. Instructions were clear. We had a nice stay in Pittsburgh. Thanks Ryan.
Top Guest favourite
Apartment in Pittsburgh
4.95 out of 5 average rating, 277 reviews

The Pittsburgh Suite *Free Parking, 10mins-DWNTWN

FengdiRating, 5 stars3 months ago
We stayed at Tyler's place for a month. The place is spacious, very clean and comfortable. Tyler was very responsive to any questions we had. We appreciate the privacy and quietness as well. We did a lot of research before choosing Tyler's place, and the stay was beyond our expectation.
Guest favourite
Home in Squirrel Hill South
4.76 out of 5 average rating, 49 reviews

Squirrel Hill Elegant Bright House

RobynRating, 5 stars1 month ago
Second time we stayed here. Great home, great host, great communication. Highly recommend!
Guest favourite
Home in Pittsburgh
4.93 out of 5 average rating, 43 reviews

5-BR Home (Sleeps 10) Close to Oakmont/Downtown

MichaelRating, 5 stars7 months ago
Having stayed in a number of Air BnBs over the years, Heidi’s home moves to the top of the list of favorites! We really appreciated the opportunity to stay in Heidi’s beautiful home, where we were treated with kind hospitality. The house is even better than in the photos, so lovingly maintained, with incredible original woodwork and stained glass. After a day of activities in the Pittsburgh area, it was fantastic to come back to this amazing house, which is super comfortable and homey. Not only was the house great, but Heidi provided us with food! It was so awesome to have fresh coffee and a nice breakfast in the morning. She also gave us helpful suggestions for area restaurants and brew pubs within walking distance. I especially loved the front porch for taking in the night air on the porch swing…We highly recommend this beautiful home!
Superhost
Apartment in Greenfield
4.78 out of 5 average rating, 143 reviews

Beechwood BNB

RedaRating, 5 stars3 months ago
Rebecca’s place was a very comfortable and spacious living area. We were in and out a lot due to being there for a funeral and had no issues with parking or entering home. Kitchen was well stocked and linens were clean and abundant. We were able to walk to a restaurant and grocery store which was very convenient. It had a wonderful large front porch. Very satisfied overall with our stay!
Superhost
Apartment in Mount Washington
4.87 out of 5 average rating, 461 reviews

View, Off Grandview Drivewy Parking! Mt Washington

DanielRating, 5 stars1 month ago
charming old place. Perfect for access to the statium and restaurants. Great host communication. The view is a nice bonus!
Superhost
Home in Bloomfield
4.65 out of 5 average rating, 246 reviews

👑King Bed⚡ Quiet ‧ West Penn🏥 Parking 🐶Pets

AndersonRating, 5 stars2 months ago
It was wonderful spot, a lot of restaurants and things to do in walking spots. Neighbors were really friendly and helpful! Michael was super understanding and communicative. We ran into a problem he helped.
Top Guest favourite
Cabin in Pittsburgh
4.93 out of 5 average rating, 158 reviews

Cabin in Pittsburgh. 20 minutes to Pittsburgh

WilliamRating, 5 stars3 days ago
We came into town for the US Open. Cabin was easy to find and a great location for us to get to the tournament. Diane was very responsive to any message. Loved the peacefulness of the cabin. We enjoyed sitting on the deck and watching nature. Thank you Diane.

Family-friendly home rentals with Wi-Fi

Guest favourite
Home in North Side
4.95 out of 5 average rating, 306 reviews

Michael's Place

GregRating, 5 stars1 week ago
Michaels place was just as listed. It was perfect for our overnight stay. Perfect location for what we needed! Michaels instructions were perfect and very helpful. Will definitely stay here again if in the area in the future.
Top Guest favourite
Home in Bellevue
4.99 out of 5 average rating, 86 reviews

Grand on Grant

ThomRating, 5 stars2 weeks ago
Our family of four (two parents, two 20-something’s) stayed for a long weekend for a wedding. It was convenient to drive into the city in 10 minutes and so peaceful to be away from the city, too. We all agreed we’d be happy to live in this spacious, well-decorated and lovely home. The front porch swing was my spot for breakfast, while others liked the screened-in back porch. The nights were chilly outside but we were warm in the house. Kitchen is adequate size for our needs and there were a lot of good quality knives, pots and pans, and dishes. We would definitely stay again!
Top Guest favourite
Apartment in Squirrel Hill South
5 out of 5 average rating, 61 reviews

Thoughtful, Furnished, Convenient in Squirrel Hill

FrankieRating, 5 stars1 month ago
This house was very comfortable. We were delighted with the box of fresh bakery items. On a previous trip we had tried to visit this bakery, but the line to get in was too long. There was a fresh blooming plant on the dining table. We enjoyed the front porch, and the proximity to the residence of our mother. The location, just off Murray Ave., is ideal. We found many interesting shops and restaurants. We well return to this rental on our many visits to Mother.
Top Guest favourite
Guest suite in Friendship
4.98 out of 5 average rating, 253 reviews

Large victorian 3rd flr apt in walkable eastend

CaramiaRating, 5 stars1 month ago
Beautiful place with lots of interesting details. Great location, super clean, comfortable beds and well supplied. I would absolutely stay again and recommend it.
Top Guest favourite
Home in Bloomfield
4.98 out of 5 average rating, 197 reviews

PBR - Pittsburgh Bloomfield Rowhouse

JeffreyRating, 5 stars5 months ago
Absolutely one of the best Airbnb experiences we’ve had. Jeff and Melissa were very accommodating and have a beautiful home. It was very clean and extremely spacious. The cupcakes they provided- seemingly a small gesture- was a nice touch. We will definitely consider staying there the next time we visit Pittsburgh.
Guest favourite
Home in North Side
4.84 out of 5 average rating, 172 reviews

Walk to downtown, stadiums

JackieRating, 5 stars3 weeks ago
This was our third time staying at Keili’s place. We love the charm of the old row house, and it’s so convenient to things we want to do downtown. Keili is always a great host, and very responsive if ever we need help.
Superhost
Home in North Side
4.83 out of 5 average rating, 409 reviews

Adorable North Side Carriage House

BritRating, 5 stars1 week ago
Amazing bang for your buck. Older style home great for two couples (4ppl max). We didn’t have to take a single uber to see everything we wanted to see (strip district, PNC park, Acrisure and casino too!! Cute park and coffee shops near by. Smaller quarters but worked for us !! Would definitely be back! Thank you !
Superhost
Home in Bloomfield
4.89 out of 5 average rating, 252 reviews

Cozy home in "Little Italy"

TraciRating, 5 stars1 week ago
Rita's place was just like she described it - clean, great location, amenities and more. She had recommendations for restaurants, shopping in the area, but we are very familiar with her locale. Her home was convenient for us as our son lives nearby - was nice to be so close. Bloomfield neighborhood is friendly, quiet and safe. Easy walk to main street that has many shops and restaurants. Rita was very quick to respond to my inquiries and very helpful with questions we had. Would definitely stay again at Rita's.

Quick stats about holiday rentals that are family-friendly in South Side Flats, Pittsburgh

  • Total rentals

    170 properties

  • Nightly prices starting at

    $15 AUD before taxes and fees

  • Total number of reviews

    12K reviews

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    170 properties include access to Wi-Fi

Destinations to explore