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Family-friendly vacation rentals in South Side Flats, Pittsburgh

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in South Side Flats, Pittsburgh

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Apartment in Pittsburgh

4.86 out of 5 average rating, 646 reviews

South Side Flats - Central to everything!

Artfully decorated, large, and open concept 1 bedroom apartment in the center of the South Side Flats entertainment district. Everything you need is within steps of your front door - restaurants, grocery, and entertainment. 5 min from downtown & within 15 min to anywhere in the city. IMPORTANT: This listing is exclusively for people visiting Pittsburgh. DO NOT book with us if you live in Allegheny County without 1st receiving permission from the host, or your reservation will be cancelled.

Feb 21 – 28

R1,696 ZAR per night

Apartment in Mount Washington

4.98 out of 5 average rating, 332 reviews

☆"Million Dollar View at a Terrific Price!" ☆

"Wow wow WOW! The view from the back deck actually moved me to tears, when day turned to night, it is a million dollar view for a terrific price." --Vanessa, guest review. Veteran owned, tri-level home top floor, newly furnished and professionally cleaned. This location is great for couples, business travelers, and families. Located on Mt. Washington, it is steps from the Monongahela Incline, Grandview lookout, bars, restaurants, and Shops of Shiloh Street. Best quality and value in area!

Jun 10 – 17

R2,960 ZAR per night

Home in Squirrel Hill South

4.92 out of 5 average rating, 264 reviews

Upscale Modern 2 BR Apartment

This spacious, newly renovated, fully equipped and private access apartment was built for your enjoyment! The granite counter tops and porcelain tiled shower are a hint of the luxuries throughout. You can park on the property or on the street. Located in the heart of Squirrel Hill, right near Schenley park, the Squirrel Hill business district and bus lines. Easy Access to Bakery Square, Shadyside, Waterfront, Downtown, Museums & Galleries, Universities, hospitals, and all Sports venues.

Oct 20 – 27

R2,451 ZAR per night

Apartment in Pittsburgh

4.95 out of 5 average rating, 241 reviews

The Pittsburgh Suite *Free Parking, 10mins-DWNTWN

*PLENTY OF FREE STREET PARKING* 1 BDRM apt in the up and coming town of Bellevue, just a 10 min drive to downtown and the stadiums. This is a 2nd floor unit in my 100+ year old four-square home. It has a private entrance with a keypad for Airbnb guests, there are 2 other units in the building. Its in walking distance to public transit, shops, restaurants, places of worship, banks, and a grocery store. Pet friendly ($50 fee) just add your pet under pets in the guest section when booking.

Sep 25 – Oct 2

R2,174 ZAR per night

Townhouse in Pittsburgh

4.93 out of 5 average rating, 320 reviews

Charming Home • Vibrant Neighborhood

Enjoy a quiet night's rest just steps away from the city’s best shops, restaurants, and nightlife in the historic South Side neighborhood. Walk to Pittsburgh’s major attractions or take advantage of our public transport options and Great Allegheny Passage (GAP) trail to explore the city. Our professionally managed home accommodates groups, has free parking, and is spacious and clean. Weekday special rates available for smaller groups. You will love your comfortable home away from home!

Oct 30 – Nov 6

R4,491 ZAR per night

Apartment in Pittsburgh

4.95 out of 5 average rating, 391 reviews

Charming cozy apartment with deck.

This little jewel of an apartment is charming and cozy, with private entrance, 1 bedroom, small sitting area, fully-equipped kitchen, bath, laundry access, wifi and private deck. We are on a quiet shady street near 644-acre park. 2.5 miles to universities, 1 mile to Bakery Square. NO CLEANING FEE, so a better value than other listings! Comfortable queen-sized bed with memory foam mattress topper. Many nice amenities and original artwork. Small but homey with lots of little luxuries!

Mar 18 – 25

R1,560 ZAR per night

Home in Pittsburgh

5.0 out of 5 average rating, 209 reviews

High-End South Side 4 Bedroom House, sleeps 15!

Newly Remodeled, Gorgeous High-End 4 Bedroom, 3 Full Bathroom entire house in the heart of Pittsburgh's historic South Side neighborhood; SLEEPS UP TO 15 PEOPLE; Pets welcome; Private/Enclosed Patio Hardwood floors, raised tin ceilings on first floor; open floor plan living room/kitchen with stainless-steel appliances, marble-counter-tops, Keurig, 70 inch TV, WiFi, Convenient 2nd floor laundry facilities,HD Televisions in every bedroom w/ Cable, Luxurious Memory Foam Beds

Aug 28 – Sep 4

R11,374 ZAR per night

Apartment in Pittsburgh

4.97 out of 5 average rating, 310 reviews

Apartment: Home Sweet Home

Enjoy yourself in a bright, one floor living space, with a separate bedroom, (Queen Size bed), bathroom (shower) and living room. Sleeps 4 comfortably. Queen size sofa bed in living room sleeps 2. Private entrance with lock box and private off street parking. 6 miles from Downtown Pittsburgh sports and activities. Close to shopping, pizza and restaurants. Uber available. Enjoy sweet bread or muffins with coffee or tea to begin your stay! We are happy to meet your needs!

Aug 6 – 13

R2,585 ZAR per night

Home in Pittsburgh

4.97 out of 5 average rating, 154 reviews

Luxe Home★ Amazing Yard★ Firepit★ 2 Rooftop Decks

Pittsburgh's premier, top of the line Airbnb! No expense was spared outfitting our 4 bedroom, 2.5 bath home! Amenities galore both indoors & out with 3 large outdoor spaces, fire pit, and garage parking. Every high end detail has been meticulously selected and designed. Take advantage of all the city of Pittsburgh has to offer in the lap of luxury with your own centrally located private residence on the North Side, complete with a Peloton for the healthy-minded!

Mar 20 – 27

R9,993 ZAR per night

Apartment in Pittsburgh

4.87 out of 5 average rating, 281 reviews

Cozy + Modern apartment near the city!

*PLEASE BE HONEST ABOUT THE NUMBER OF GUESTS* *Pets are welcome! 🐶🐱$40 one time fee. I have a pet bed, bowls, & leash available. This bright & modern two level apartment is ideal for a stay near the city! Located in Uptown, it's on a quiet & mostly residential street near UPMC Mercy Hospital & Duquesne University - short walk to PPG Paints Arena. Clean & comfortable, you'll feel right at home in a place that makes navigating around Pittsburgh a breeze.

May 28 – Jun 4

R1,989 ZAR per night

Apartment in Pittsburgh

4.97 out of 5 average rating, 378 reviews

Modern Love Apartment - Heart of Lawrenceville!

This private apartment (with it's own entrance) is on the lowest level of our house. It is walking distance to the best of lively Lawrenceville. It is centrally located in Pittsburgh and close to downtown, the universities and the stadiums. We are right off of Butler Street which is where the shops and restaurants are located. There is free street parking directly in front of the house. Dozens of restaurants and shops are just a short walk away.

Aug 24 – 31

R2,456 ZAR per night

Home in Bloomfield

4.88 out of 5 average rating, 422 reviews

PRIVATE MINI STUDIO (D2)

This Mini Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, sleeper sofa, a kitchenette and a full bathroom with a private entrance on the 3rd floor of a beautiful 1890s Pittsburgh mansion. It's the size of a large room and works very well with guests that are planning to work, or go out enjoying the city and come back to a safe, clean and comfy place to recharge for the night (not suitable for kids under 10).

Aug 23 – 30

R1,846 ZAR per night

Vacation rentals for every style

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

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest suite in Highland Park

4.84 out of 5 average rating, 206 reviews

Entire private floor (giant Jacuzzi with shower!)

Jun 5 – 12

R2,309 ZAR per night

Home in Squirrel Hill North

4.91 out of 5 average rating, 143 reviews

My Favorite Sunny Bunny Eco Luxe Stay (Blue)

Jun 30 – Jul 7

R9,808 ZAR per night

Bungalow in Oakmont

4.96 out of 5 average rating, 53 reviews

Oakmont home with private hot tub

Oct 21 – 28

R5,107 ZAR per night

Home in Pittsburgh

5.0 out of 5 average rating, 10 reviews

Luxe Shadyside Spa + Parking + 5 Beds + Zen Garden

Jan 19 – 26

R7,405 ZAR per night

Chalet in Champion

4.55 out of 5 average rating, 62 reviews

Tall Cedar Chalet is a rustic, private 1 acre home

Jul 21 – 28

R4,281 ZAR per night

Cabin in Champion

4.67 out of 5 average rating, 149 reviews

4BR Seven Springs Cabin + BIG Hot Tub

Jan 15 – 22

R9,319 ZAR per night

Bungalow in Oakmont

4.98 out of 5 average rating, 64 reviews

Oakmont Home with Hot Tub

Oct 21 – 28

R3,811 ZAR per night

Home in Pittsburgh

5.0 out of 5 average rating, 18 reviews

Luxe Shadyside Victorian★Central★ Park free★8 beds

Nov 5 – 12

R13,355 ZAR per night

Family- and pet-friendly home rentals

Cabin in Pittsburgh

4.92 out of 5 average rating, 127 reviews

Cabin in Pittsburgh. 20 minutes to Pittsburgh

Mar 8 – 15

R2,924 ZAR per night

Home in Monroeville

4.84 out of 5 average rating, 141 reviews

Mayberry Escape

Nov 2 – 9

R6,364 ZAR per night

Home in Pittsburgh

4.91 out of 5 average rating, 11 reviews

House 3bed Free Parking Walk to Bars & Shops

Jul 9 – 16

R4,976 ZAR per night

Townhouse in Pittsburgh

4.88 out of 5 average rating, 99 reviews

Modern/Industrial Townhouse in Lawrenceville

Aug 31 – Sep 7

R1,771 ZAR per night

Townhouse in Pittsburgh

4.75 out of 5 average rating, 305 reviews

Rooftop Tranquility! 2-Car Garage! Sleeps 2-12!

Dec 16 – 23

R6,907 ZAR per night

Home in Pittsburgh

4.65 out of 5 average rating, 225 reviews

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

Aug 25 – Sep 1

R4,106 ZAR per night

Home in PITTSBURGH

4.94 out of 5 average rating, 35 reviews

Large Home Close to Everything in Pittsburgh

Jul 10 – 17

R5,208 ZAR per night

Home in Pittsburgh

4.89 out of 5 average rating, 152 reviews

Shadyside 5th Avenue Bedroom, Pvt. Bath, Pkg.

Jul 16 – 23

R2,031 ZAR per night

Family-friendly home rentals with Wifi

Apartment in Pittsburgh

4.92 out of 5 average rating, 410 reviews

Historic Charmer | Spacious | Off Street Parking

Aug 21 – 28

R2,103 ZAR per night

Apartment in Pittsburgh

4.78 out of 5 average rating, 383 reviews

Studio w/ view and street parking pass

Aug 5 – 12

R2,433 ZAR per night

Apartment in Bloomfield

4.93 out of 5 average rating, 331 reviews

Delightful Artsy & Private Apartment, East End PGH

Jun 9 – 16

R2,198 ZAR per night

Condo in Pittsburgh

4.93 out of 5 average rating, 460 reviews

Luxury Pittsburgh Grandview Ave Apt

Nov 15 – 22

R4,223 ZAR per night

Guest suite in Bloomfield

4.98 out of 5 average rating, 233 reviews

Large victorian 3rd flr apt in walkable eastend

Apr 13 – 20

R2,828 ZAR per night

Apartment in Pittsburgh

4.83 out of 5 average rating, 485 reviews

Renovated top floor unit! Close to downtown!

Nov 6 – 13

R1,512 ZAR per night

Home in Pittsburgh

4.98 out of 5 average rating, 180 reviews

PBR - Pittsburgh Bloomfield Rowhouse

Oct 26 – Nov 2

R3,230 ZAR per night

Home in Pittsburgh

4.92 out of 5 average rating, 228 reviews

Cozy home in "Little Italy"

Jun 11 – 18

R3,012 ZAR per night

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

Total rentals
190 properties
Wifi availability
180 properties include access to wifi
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Pet-friendly rentals
90 properties allow pets
Total number of reviews
11K reviews
Nightly prices starting at
R185 ZAR before taxes and fees

Destinations to explore