Holiday rentals in Herrs Island

Flat in Downtown Pittsburgh

Cultural District new King Suite whirlpool tub

Experience Pittsburgh's Cultural District from this new king suite! You are surrounded by Pittsburgh's best restaurants, shops, steps away from the Convention Center, theaters, and more. Designed for comfort and convenience in an unbeatable location. - King bed - Whirlpool tub / shower - Equipped Kitchen & Laundry - Walk to everything - Mult garages within 5 min - 24/7 guest support Perfect for business trips, events, or weekend getaways. We're here for you before, during and after your stay!

4.91 out of 5 average rating, 390 reviews

4.85 out of 5 average rating, 41 reviews

Flat in North Side

Pittsburgh Modern & Cozy 1 Bdrm With Free Parking

Family oriented One Bedroom apartment with a central location in Pittsburgh. 5 mins from Downtown, NHL and NFL games, Lawrenceville Strip District. Enjoy the proximity to shopping, bars & restaurants. This apartment features 1 bedroom, 1 living room with sofa bed, 1 bathroom on the on the lower floor of a family house. Our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families only and this is NOT a party place.

4.83 out of 5 average rating, 99 reviews

A spacious living room is presented with a modern sectional sofa arranged around a wooden coffee table. Artwork in soft tones decorates the walls. Natural light enters through window coverings, highlighting the clean lines of the space. The open layout leads to a dining area in the background.

Flat in North Side

Pittsburgh Spacious & Modern 3BD APT Free Parking

Peaceful and family oriented Three Bedroom apartment with a central location in Pittsburgh. 7 mins from Downtown, NHL and NFL games, Lawrenceville Strip District. Enjoy the proximity to shopping, bars & restaurants. This apartment features 3 Bedroom, 1 Bathroom on the first floor of a family house. Stylishly setup, our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families only and this is NOT a party place.

A spacious living area features a comfortable sofa and armchair, with a large wall-mounted TV positioned nearby. Floor-to-ceiling glass doors open to a private deck, revealing lush greenery and inviting outdoor seating, creating a serene connection to nature.

4.98 out of 5 average rating, 130 reviews

Stunning PH Double King Suite w/ Rooftop Terrace

Enjoy our stunning 2 BR Penthouse suite on Butler Street, right in the heart of Lawrenceville. This is a brand new construction building in 2025. Just steps away from several local shops, cafes, and dining options in one of Pittsburgh’s most vibrant neighborhoods. ⭐2 King Beds (memory foam mattresses) ⭐1 Queen Sleeper sofa + 1 Queen Murphy Bed + Pack N Play ⭐3 private decks (+ Rooftop Deck) ⭐Free in-unit washer/dryer ⭐Free off-street parking ⭐Desk with speedy wifi ⭐24/7 guest support

The living area features a blue three-seater couch with a round rug underneath, paired with a coffee table. A kitchen island with bar stools is visible in the background, while a dining table and wooden stairs leading to an upper level are seen on the right. Natural light enters through nearby windows.

4.94 out of 5 average rating, 299 reviews

Brand New! Lawrenceville KING Suite - Huge Balcony

1 bedroom 1 bath apartment w/ a HUGE private balcony steps from Butler St in Lawrenceville neighborhood! Sleeper Sofa and extra linens for bigger groups. BRAND NEW construction! Enjoy this stylish space in the coolest neighborhood in town, steps to dozens of restaurants, shops, coffee shops. A few blocks to UPMC Children's hospital and the Strip District, short drive to Downtown, North Shore, Shadyside, Oakland, very close to Pitt, CMU, & several hospitals! Book your stay today!

5.0 out of 5 average rating, 8 reviews

Flat in North Side

Sports-Themed Retreat | Near Stadiums | Sleeps 5

Steelers, Pirates, Penguins, or Pitt game? Stay minutes from ALL stadiums—easy access, no downtown parking stress. Enjoy unique 2BR sports-themed retreat in historic Troy Hill! Acrisure • PNC Park • PPG Paints Arena nearby Cool sports vibe, clean, and comfortable! Shared backyard w/ river view (outdoor only). Walkable area across from Hill Topper’s Pub + food spots. Essentials: ✔ Free street parking ✔ Self check-in (smart lock) ✔ Fast WiFi + workspace ✔ Coffee & tea ✔ Air fryer

Superhost

A living area is highlighted, featuring a light-colored sofa and a stylish glass coffee table. A large television is positioned against a dark media console. Two windows provide natural light, complemented by soft drapes. A decorative wall adds texture to the inviting space.

Home in North Side

3BR Home King Bed + Fenced Yard Near Sports & City

Cozy and Central! Minutes to the Strip, Downtown & Stadiums. PET FRIENDLY 3-bd, 1-ba home is the perfect blend of modern amenities, welcoming vibes, and pet-friendly accommodations. Inside, you’ll find three bedrooms, a sophisticated bathroom, and an open-concept living area that’s ideal for lounging. The fully-equipped eat in kitchen features sleek appliances. Step outside to discover the real highlight—a fully fenced in double (city) lot that offers a space for your pets to roam.

4.75 out of 5 average rating, 52 reviews

4.89 out of 5 average rating, 37 reviews

Home in North Side

One Wild Place - Fun 4BR 2Bath/Firepit

Welcome to our stylish and unique Airbnb, inspired by the vibrant spirit of the Pittsburgh Zoo! Located in the heart of Troy Hill, this roomy vintage space combines playful animal décor with traditional row-house design, creating an unforgettable stay. Whether you're here to explore the city or just enjoy a comfortable, one-of-a-kind retreat, our zoo-inspired theme offers a fun and welcoming atmosphere for all. Experience the wild side of Pittsburgh, right from your doorstep!

5.0 out of 5 average rating, 84 reviews

Artsy studio in Lawrenceville: easy & free parking

Once a bustling Lawrenceville storefront, this 100+ year-old building is now a one-of-a-kind studio retreat in the heart of the city. Soaring 14-foot ceilings, exposed brick, a hand-painted mural, and tons of natural light give the space serious wow factor. When it’s time to recharge, tuck away in the cozy sleeping nook and shut out the city. Step outside and you’re minutes from Pittsburgh’s best dining, coffee, shops, and breweries—with free street parking right outside.

Superhost

An open living area is highlighted by a cozy couch with patterned pillows, facing a flat-screen TV. Exposed brick walls add texture, while wooden floors provide warmth. A glass railing leads to the staircase, creating a modern feel that complements the natural light from the windows.

Townhouse in Strip District

Charming Getaway: Off-Street Parking, Walkable

You can experience Pittsburgh like a local in this beautifully updated row house, ideally located just a 10-minute walk from two of the city's most vibrant neighborhoods: Lawrenceville and the Strip District. The house includes free off-street parking for your convenience, a rarity for this part of town. Stay connected with lightning-fast Wi-Fi and take advantage of the dedicated workspace, perfect for remote work or planning your Pittsburgh adventures.

4.88 out of 5 average rating, 405 reviews

4.93 out of 5 average rating, 434 reviews

An inviting private hot tub is situated in a fenced backyard area, surrounded by soft lighting and decorative plants. The brick wall of the house provides a rustic backdrop, creating a cozy ambiance at dusk.

Townhouse in Pittsburgh

Hot Tub, King Bed, Cabin Vibes in Lawrenceville!

With cozy cabin vibes, exposed brick, and designer touches, this romantic getaway is perfect for couples or a relaxing stay. Escape to a rustic-modern retreat in the heart of Lawrenceville, just one block from Butler Street! Unwind in the private hot tub, snuggle up on the couch by the fireplace, or explore the city's best dining and nightlife just steps away. Completely remodeled in January 2025 with luxe amenities—book now for an unforgettable stay!

A cozy living area features a soft gray couch adorned with patterned throw pillows. A round black coffee table sits on a striped rug. A desk with a chair is positioned near a window with white blinds, and decorative wall art adds character to the space.