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Vacation rentals in South Side Flats

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Top-rated vacation rentals in South Side Flats

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Top guest favorite

A modern three-story home is shown, featuring large glass windows that allow ample natural light. The exterior showcases a combination of sleek metal siding and neutral tones, with a driveway leading up to the garage. Two neighboring buildings are visible on the right.

Home in Pittsburgh

5 out of 5 average rating, 47 reviews

3 King Beds! Garage! Theater! Great Location!

Perfect for families & traveling groups of friends, our new construction home is ready for its first guests! All three bedrooms have king beds along with a private attached bathroom, perfect for travelers wanting privacy. No need to search for parking, with garage + driveway parking for 2 vehicles. Create a memorable meal in our well stocked kitchen, relax on the couch and watch the 120" screen, or take a short stroll to the numerous bars & restaurants in the area. You can't beat this location!

An expansive outdoor deck features a sectional seating area with soft cushions, a coffee table, and a dining set. A fire pit with adjacent seating is visible, along with a patio heater. Potted plants add greenery to the space, enhancing the tranquil atmosphere.

Apartment in Pittsburgh

5 out of 5 average rating, 9 reviews

Wow! Skyline Sunset Escape On Hackstown

Ahoj and welcome to your elegant 2-bed, 1.5-bath home with breathtaking downtown views! Newly renovated with a thoughtfully designed interior, this home offers a distinctive experience. Enjoy parking in a 2-car garage plus an outdoor space, and easy access to downtown and Oakland. Featured on the South Side Historic Homes Tour, it’s a true Pittsburgh gem. Pets are allowed! Relax on the deck with a fire pit, or unwind by the custom mosaic fireplace with a 55” TV or in the luxurious soaking tub.

Home in Pittsburgh

4.91 out of 5 average rating, 64 reviews

Modern Spacious Cozy Home

We do our very best to provide you with a comfortable, and clean home during your stay! Free street parking usually with plenty of space available for multiple cars. House is located on a nice and quiet street. 5 minutes from southside. 15 minutes from downtown. WiFi and smart T.V In living room. Washer & dryer with pods and dryer sheets. Closets in bedrooms. Kitchen has everything you will need, plus coffee maker with coffee pods and creamer. kid friendly dishes too. Lots of outdoor sitting

Home in Pittsburgh

4.94 out of 5 average rating, 164 reviews

Huge 6 BDRM min to Downtown & Stadiums w/ parking

Gather with friends and family in our renovated Pittsburgh home, designed for comfort and fun! ✅ 6 Large Bedrooms & 3 Full Baths – Includes a soaking tub ✅ Easy Parking – Two-car driveway + plenty of free street parking ✅ Stocked Kitchen – Fully equipped with essentials ✅ Spacious Living Areas – Two living rooms for lounging ✅ Entertainment – Projector & sound system for movie nights ✅ Family & Pet-Friendly – Room for everyone ✅ Cozy Fireplace – Available Nov.–Feb. Everyone will enjoy it!

An exterior view of the home is presented amidst vibrant autumn foliage. The multi-story structure is surrounded by trees showcasing various warm colors, complementing the peaceful nature setting. Large balconies offer views of the surrounding landscape, enhancing the serene atmosphere.

Apartment in Pittsburgh

4.98 out of 5 average rating, 120 reviews

Amazing views! Free Parking!

After a year-long restoration project, we are thrilled to present our home in Pittsburgh's historic north side. What awaits you is a quiet, downtown gem surrounded by nature with amazing city views. What You'll Love: -Total and complete renovation between 2020-2021 -Gourmet, fully-equipped kitchen including coffee/tea station -Remarkable city views -Close to stadiums, downtown, museums -Relaxing patio -Gigabit internet connection -Peaceful nature surroundings -Comfortable memory foam beds

Top guest favorite

A comfortable living area features a dark leather sofa and an accent chair with a geometric pattern. Light spills in from a doorway leading to the dining area, where a wooden table is set for four. Decorative elements include a coffee table and wall art.

Home in Pittsburgh

4.97 out of 5 average rating, 398 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.

The dining area features a wooden table set for six, surrounded by matching chairs. A decorative area rug lies beneath the table. In the adjacent living space, a sofa and a chair invite relaxation, with large windows providing natural light.

Home in Pittsburgh

4.95 out of 5 average rating, 91 reviews

Cozy, Pet-Friendly Home in Pittsburgh South Side

Welcome to Steel City! Our updated two-bedroom house in the lively South Side is a perfect home for your group to relax and unwind including your four-footed friends! After exploring the city, enjoy the mood lighting on our cozy patio or check out the local restaurants and bars within walking distance. Work from home with a desk space in each bedroom. Our home has everything you will need and a perfect location if you're looking to have a truly authentic Pittsburgh experience!

Apartment in Pittsburgh

4.96 out of 5 average rating, 174 reviews

Free Parking★ Walk Everywhere ★North Side Gem!

You'll walk in and say wow! Our place has exposed brick throughout, a generous open floor plan, soaring ceilings, a spacious bathroom and two cozy bedrooms - king & queen 12" thick mattresses. Work from home at your desk, whip up a cocktail or meal in the full kitchen, or lounge on the couches and watch a movie or browse the web (1 Gbps). It's a short walk to Allegheny General and a few minutes to the bars & restaurants and stadiums on the North Shore - it's a great location!

A staircase with a wooden banister ascends from the main floor, flanked by exposed brick walls. The space transitions into an open dining area, featuring a dark wooden table with multiple chairs. Warm lighting highlights the hardwood flooring and modern kitchen in the background.

Home in Pittsburgh

4.99 out of 5 average rating, 147 reviews

The Larrybird Inn - Steps from Butler Street!

The Larrybird Inn is situated in the heart of Lawrenceville, in a beautifully restored home over 100 years old. Park your car for the weekend and enjoy the neighborhood and other surrounding areas by foot or bike. Walk to nearby bars, restaurants, see a movie all within hundreds of feet away! There is also Arsenal bowling lanes across the street! We invite you to stay in our home, one of the most charming Airbnbs in Lawrenceville.

A stunning view of Pittsburgh's skyline is captured at dusk, showcasing buildings illuminated by city lights. The sky transitions through shades of orange and blue, while the rivers reflect the colorful light. A quiet street is visible in the foreground.

Apartment in Pittsburgh

4.66 out of 5 average rating, 85 reviews

City Escape/Mt Washington/4 Beds · Free Parking

Upscale Apartment in the heart of Pittsburgh's Mount Washington, located half a block off the city's most desirable viewpoint - Grandview Avenue! · 3 BR/ 1.5 BA - 5 beds - Sleeps 9 · Long-term & Family-Friendly - inquire for discounts! · Street Parking · Convenient & Safe Location · Self Check-in w Keypad in rear of building * Minutes drive time to football/baseball/hockey stadiums, museums and universities.

Home in Pittsburgh

4.94 out of 5 average rating, 78 reviews

Sweet Mt. Lebo Cape Cod Retreat

Kick back and relax in this calm, stylish 1940s Cape Cod home. We spent the last two years upgrading the residence which features a brand new kitchen, dining room, main floor bathroom, and mid-century modern furniture throughout. This house sits on a very quiet cobblestone street with little to no traffic. Deer can be seen on your walk to Starbucks a mere 7-10 minutes away.

The front porch features direct access to the apartment, showcasing wooden flooring and inviting blue doors. A welcome mat lies at the entrance, and a swing can be seen in the background, enhancing the outdoor seating space.

Apartment in Pittsburgh

4.9 out of 5 average rating, 49 reviews

Historical charm - 1bedroom spacious apartment

This one bedroom apartment is for anyone looking for a quick getaway in town or for a longer stay. The space is clean & spacious. We offer a queen bed & a sleeper sofa , a full kitchen and a full bathroom. The space 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.

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Popular amenities for South Side Flats vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in South Side Flats

The image captures a panoramic view of the city skyline at sunset, with colors transitioning in the sky. A wooden deck, adorned with string lights, extends over the scene, while lush greenery frames the foreground, providing a contrasting natural element to the urban landscape.

Home in Pittsburgh

5 out of 5 average rating, 7 reviews

Spacious home with great views

A spacious living area features high ceilings adorned with original pendant lights. A comfortable sectional sofa is placed around a circular coffee table on a soft rug. Two plush armchairs are positioned nearby. The stylish spiral staircase leads to the upper level, and large windows allow natural light to fill the room.

Home in Heidelberg

5 out of 5 average rating, 36 reviews

Glendale Chapel

A modern bathroom showcases elegant marble walls with a striking vein pattern. A sleek vanity with a square sink is complemented by a tall mirror and minimalist fixtures. A separate shower area features a rainfall showerhead and a black handheld fixture, with a small plant adding a touch of greenery.

Home in Pittsburgh

4.91 out of 5 average rating, 53 reviews

Private Parking • Charming Getaway

A spacious living room is highlighted by a comfortable sofa with decorative pillows and a wooden coffee table. Elegant windows allow natural light to brighten the space, complemented by a flat-screen TV and a decorative fireplace. A cozy armchair enhances the inviting atmosphere.

Apartment in Pittsburgh

4.93 out of 5 average rating, 30 reviews

Spacious 1 bd in Shadyside - Walk to CMU and Pitt

A modern wall sconce is mounted on a textured gray wall, featuring a cylindrical light fixture that directs illumination downward. The design is minimalistic, with a sleek shape and a subtle switch panel below the light source. Light is softly cast onto the wall, enhancing the area.

Home in Pittsburgh

4.76 out of 5 average rating, 17 reviews

*NEW*Near Butler St- 2 King Beds

A sectional sleeper sofa featuring colorful throw pillows is positioned against a bright orange accent wall. A white coffee table sits in front, complemented by a small potted plant. Natural light reflects off a large mirror above the sofa, enhancing the space's openness.

Apartment in Pittsburgh

5 out of 5 average rating, 3 reviews

2 Full Apartments, 4 Bedrooms w/ 11 beds + Parking

An expansive common area is shown featuring a billiards table at its center. Surrounding spaces include stylish seating arrangements, built-in shelves displaying decor, and a range of windows allowing natural light to brighten the wooden floors.

Apartment in Pittsburgh

4.89 out of 5 average rating, 140 reviews

Luxury Apartment with Balcony Near Stadium

Home in Pittsburgh

4.91 out of 5 average rating, 45 reviews

Family Home | Ping-Pong | Parking | Sleeps 13

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