Holiday rentals in Shadyside, Pittsburgh

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.

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

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!

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.

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!

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!

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.

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.

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.