Holiday rentals in Pittsburgh

Pittsburgh, PA - North Side

Keep it simple at this peaceful and centrally-located place. This two bedroom single family home is in an optimal location for access to all Pittsburgh has to offer. Located 2 miles from Pittsburgh's downtown area and Strip District, 5 minutes from PNC Park and Heinz Field, 10 minutes from PPG Paints Arena and UPMC Hospitals, and 15 minutes from CMU, University of Pittsburgh, and Duquesne University. Minutes from Garden Cafe coffee shop, Threadbare Cider House and plenty of bars and restaurants.

Urban Oasis Home - Hot Tub, Pet-friendly, Koi Pond

This charming historical home is close to everything! You can be downtown within 5 minutes. You'll be minutes from the stadiums, museums, and the casino! Pamper yourself. Relax in the hot tub while listening to the sounds of the waterfall over the pond. Watch the colorful Koi splash and play. The meticulously landscaped grounds have countless surprises and beauty in every season. You will enjoy every comfort in this luxurious three-bedroom and 2.5 baths. There's even a shower for your furbaby!

Cliffside Luxury with Spectacular City Views

Amazing views, rooftop patio w/fire pit, contemporary design and furnishings are just the beginning for your amazing stay at our cliffside paradise. This architecturally stunning home offers a fully equipped kitchen, two decks to dine and relax on. Beyond its walls, you can visit the nearby Station Square shops and restaurants, 2 Inclines, Pittsburgh Zoo and PPG Aquarium, Warhol Museum, the Rivers Casino, or watch the Penguins at PPG Arena, Steelers at Heinz Field, and the Pirates at PNC Park!

Stunning King Suite |Unbeatable Downtown Location!

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!

Huge Open Concept 2BR by Walnut

HUGE apartment In the heart of Shadyside w/ room for the whole family! 1 Block to Walnut St & FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 2 floor apt in a prime location, w/ all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, & fitness studios close by. The building was gutted & remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances is brand new!

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

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.

Spectacular Skyline Views - Luxury 2 Bedroom

Watch the city skyline buzz from the comfort of your couch or bed. This high end luxury home is located on Mt. Washington and close to everything Pittsburgh. Minutes walk to Southside, Downtown, Strip District, Heinz Field, and PPG Convention Center just to name a few. Super clean, comfortable, and cool with all of the amenities of your own home. Just bring your bag and make this home base while you're in the Burgh. Great for couples, friends, solo adventurers, and business travelers.

Cozy 1BR Minutes from NFL Draft

Welcome to our newly remodeled 1 bedroom apartment, featuring modern furnishings, upscale appliances, and abundant natural light. Just steps from the David L. Lawrence Convention Center (DLCC), it's perfect for business travelers and event-goers. Enjoy nearby attractions like PNC Park, Market Square, and the Cultural District—all within walking distance. Whether you're visiting for business or leisure, our space provides a comfortable and convenient base for your Pittsburgh stay!

Cozy King suite! $0 cleaning fee

Brand new listing! 1 BR/ 1 bath apartment in a prime location steps away from Walnut street with plenty of restaurants, shops, coffee shops & UPMC Shadyside hospital! Fully equipped for both long and short stays. - King bed (memory foam mattress) - Sleeper sofa - 24/7 Guest communication - Pet friendly - Fully stocked kitchen - Smart Home Technologies - Central AC/ Heat - Free street parking - Speedy wifi & desk - Free washer/ dryer Message today to secure your reservation!

Friendship Retreat~B | 1BR w/ Gourmet Kitchen

Enjoy a stylish first-floor 1BR with a gourmet kitchen featuring high-end appliances and a spacious living area perfect for relaxing or entertaining. The queen-size bedroom offers a comfortable night’s sleep. High-speed WiFi and a dedicated workspace make it ideal for business travelers or remote work. Access to shared parking (6 spots, first-come, first-served). Located near West Penn Hospital and UPMC Shadyside, perfect for couples, visiting families, or medical stays.

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!