Holiday rentals with outdoor seating in Pittsburgh

Luxury Mountainside with Spectacular Views

Furnished by West Elm and RH (Restoration Hardware) to deliver a one of a kind luxury experience. Amazing views, two huge patios, one with a concrete propane fire-pit, modern design and furnishings are just the beginning of your amazing stay at our cliffside paradise. This architecturally stunning smart home offers a fully equipped chef's kitchen, and the highest end furnishings to make this the perfect getaway. Have a Tesla? Bring your charger to plug into our 220V outlet at the driveway!

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.

Cozy King Bed Suite ~ Free Parking & Ground Floor!

Enjoy our cozy king bed suite located in the safe, central Friendship neighborhood. This newly renovated retreat is just a short distance from all that Pittsburgh has to offer! Steps away from Whole Foods and short walk to Yinz Coffee shop! ⭐King bed (Memory foam mattress) ⭐Queen pull out bed ⭐Pack n play ⭐First floor w/ no steps ⭐In-unit washer/ dryer ⭐Large desk w/ speedy wifi & extra monitor ⭐Pet friendly ⭐24/7 Guest support ⭐Free off-street parking ⭐Close to CMU/ Pitt!

Shadyside/Pittsburgh, Modern & Cozy 1BD w/Prkng

Modern and family oriented 1 Bedroom apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment features 1 Bedroom & Dining area and FREE Parking. 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, executives, expats and this is NOT a party place.

Walk to CMU, Pitt, Shadyside! King Suite! Parking!

This remodeled apartment is in an ideal location in Shadyside close to CMU, Pitt, Walnut Street and much more! My apartment features a deck, open-concept layout, bedroom with a walk-in closet, central air, and free laundry. One parking spot is available for free if you reserve it in advance. The apartment sleeps 4 people. The bedroom has a king bed. The living room has a sofa couch that very conveniently folds down to transform into a queen-sized bed.

"The Spa Room" Renovated Flashlight Factory

Beautiful 1700 sq ft loft apartment. Located in historic north side. Minutes from both the stadiums, night life, casino, and museums! Best suited for 2 but can accommodate 4. Hard wood floors. Exposed brick. Huge state of the art kitchen. Beautifully executed bathroom with a walk in shower and massive soaking tub. If the bathtub isn't enough for you there is a hot tub located in the light well 1 floor down from the loft. Our other AirB&B is a Plus.

Cool, Vintage Design | Walk to AGH | Park Free

You’ll walk in and say wow! This bright 3-story row home combines soaring ceilings, an open floor plan, and a stunning spiral staircase for that Insta-worthy moment. Unwind in two comfy bedrooms, refresh in a large, uniquely styled bathroom, and enjoy a nicely stocked kitchen. Tucked on a quiet street near Allegheny General, it’s an easy walk to the North Shore’s bars, restaurants, and stadiums—perfect for work or play in Pittsburgh!

Business Suite | Walkable Entertainment

Location, Spacious Workplace, and Walkability! Welcome to our first Business Suite. This beautiful apartment has prime-location, workspace luxury full bathroom with a double sink, and spacious living. We at GroupStay continue to provide an excellent experience for our guests providing all amenities and excellent customer service. We take pride in our communication and your comfort is our mission!

Master Suite central to PGH and Airport Top 5%B&B

Welcome to Birds&Bees — Your cozy escape just 7 minutes from Pittsburgh! Unwind in this modern, pet-friendly retreat featuring a dreamy bed, comfy sectional, and a fully stocked kitchen with free snacks and drinks. Perfect for couples, solo travelers, or small families—comfort, style, and convenience all in one place. 📍 Ideal location 🐝 Themed interior 🐶 Pet friendly ✨ Modern touches

2BR Near the NFL Draft – Great Location

Located in the heart of the lively Cultural District, our spacious and stylish loft offers both elegance and convenience. ✅ Stunning city-wide views from the rooftop (Public/Shared) ✅ Steps away from sports venues, restaurants, and nightlife Enjoy ultra-fast Wi-Fi, family-friendly amenities, and a secure, peaceful environment. Book now for an unforgettable Pittsburgh experience.

Spacious KingSuite by WholeFoods

Spacious 1 bedroom apartment in a brand new building just a 1 min walk to the new Whole Foods! Short Walk to UPMC, West Penn, & Children's hospitals, close to CMU & Pitt, and Shadyside The building was gutted and entirely remodeled in March 2024, everything down to the soundproofing and top of the line appliances are brand new! Granite kitchen, Free laundry included inside the unit

Green Street Guest House

Enjoy a stylish and comfortable experience at this renovated home located in the Sewickley central business district surrounded by shops, restaurants and entertainment. Full brick walls and radiant heat keep it warm in winter and cool in summer. Atmospheric accent lighting, original painted artwork and eclectic whimsical decor sets a festive tone for your stay.