Vacation rentals with outdoor seating in Penn Hills

Gorgeous Southside slopes house w/outdoor hot tub

This family owned and managed, immaculate one of kind custom home overlooks the entire city from Mt Washington, downtown to Oakland and beyond. Enjoy a coffee/cocktail on the master bedroom balcony! Our outdoor areas are perfect for entertaining and BBQ's. Year round outdoor hottub Private driveway with security camera to park your cars, no more driving around looking for parking on city streets! 4.8 miles to Arenas 2.8 miles to Oakland Check out our other high end house "Pittsburgh’s Tropicana"

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!

Shadyside/Central @2 Bright &Stylish Studio w/Prkg

Bright and Stylish family oriented bright ground floor Studio apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment is a Studio with bathroom, kitchen 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.

The Sycamore BnB @ 10.7 Marina

Stay above 10.7 Marina on the Allegheny River, in Verona, PA, a little river town about 10.7 miles upriver from Downtown Pittsburgh. Enjoy a complementary kayak frompad board or canoe rental to enjoy a river adventure or dip in the Allegheny to cool off. Create your own river adventure to Sycamore Island, or Plum Creek to explore. You can also take it easy and hang out on the deck with panoramic views of this “lake like view” and enjoy the many sunsets. Eat, drink and shop many local spots.

Upscale King Bed Suite |ADA w/ Free parking!

Enjoy our spacious king-sized 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 ⭐ADA Accessible! ⭐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! ⭐$0 cleaning fee!

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.

Gorgeous Modernized Cabin + Hot Tub + Pool Table

Welcome to this incredible, fully renovated true log home with a massive entertainment room consisting of a pool table, ping pong table and more 🔥 3 full sized bedrooms along with an additional room with a pull out couch. There are 3 private bedrooms or use it as 4 with a wall separation. Fully equipped kitchen with quartz countertops and stainless appliances. Large front porch with plenty of furnishings and a rear deck with a view of a farm. Huge 2 car garage for parking and a driveway! 🚘

King Bed | Amazing Location | Stunning Design

✨Modern Nordic charm in the heart of Lawrenceville!✨ Just two blocks from Butler Street, you’ll be surrounded by Pittsburgh’s best bars, restaurants, coffee shops, & patios. This art-filled 2BR home combines thoughtful design with high-speed internet, two 55” 4K TVs, and a cozy loft office. Cook in the fully stocked kitchen, stream your favorites, or unwind in a space that’s as functional as it is stylish. Recently remodeled with comfort in mind—it’s the perfect home base for work or play!

East End Gem | Your Home Away from Home

This bright, stylish, and comfortable space, designed by an HGTV producer! With a fully remodeled kitchen and bathroom, cozy beds, and inviting rooms, this home offers the perfect home away from home. Conveniently located within 20 minutes of everything Pittsburgh has to offer, including sports fields, rivers, bridges, shopping, museums, historical sites, music venues, universities, and more! Whether you're here for business or pleasure, you'll find everything you need for a relaxing stay.

Cute Apt Minutes from Downtown and Stadiums!

🏡 Welcome to this charming home just minutes from downtown Pittsburgh & the stadiums! Perfect for couples, friends, or solo travelers. Enjoy a spacious fenced backyard, comfy living areas, and easy access to city highlights. No parties, but great vibes always. 🛋️ Inside, you’ll find a charming, thoughtfully decorated home that’s as functional as it is cute. 🌿 Out back, you’ll love the spacious fenced-in yard — perfect for sipping coffee, or unwinding after a day in the city.

New King Suite by Whole Foods!

Spacious 1 bedroom apartment in a brand new building just across the street 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! Enjoy dozens of restaurants, shops, coffee shops, and fitness studios just a walk away! Granite kitchen, Free laundry included inside the unit

The Lily Pad Cabin

Cozy cabin offers open floor plan with covered porch overlooking small pond on our property. Uniquely decorated. Views of woods & fields, but close to numerous restaurants, parks & walking trails, & TRAX Farms. The Trolley to Pittsburgh is two minutes away. Should you need single night accommodation, please message me for consideration. Also consider “Mojo’s Loft”, our pet-friendly rental or Jackson Hill Cabin, our full log home with three bedrooms & a pool table.