
Holiday rentals in Homestead
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Top-rated holiday rentals in Homestead
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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!

Steep Retreat Hazelwood Greenway
Take it easy at this unique retreat where the city and greenway meet. This 2 BD/ 1.5 BA home, built during the depression and renovated during the pandemic, boasts of these eras. It is located in the mid heights of Hazelwood just below the cemetery on a dead end street. It requires a 42 step ascent to the entrance. It has more decks than bedrooms and a hot tub that shares the lower deck with a propane grill. Nearby: Waterfront, Southside, Squirrel Hill, the City Parks and the GAP trail.

Allegheny River Aqua Villa
Experience a unique getaway on the Allegheny River with our exceptional tiny home built on a barge! This floating haven offers a distinctive reverse floor plan with luxury & breath-taking views! Lower Level- Two inviting bedrooms, each with twin beds that can convert into a king for your comfort - Full bathroom with Dual Rainfall Shower Heads. Upper Level - Open Concept Living with TV & Internet, Fully Equipped Kitchen & Peninsula. See-through gas fireplace! Patio Doors & Wrap around Decks!

Hilltop Suite, Quiet Street
You will have your own entrance & onsite parking in the driveway. Your PRIVATE area does not join with my living area in any way; we likely will never meet. The suite includes your own bathroom with a deluxe shower, an in-suite mini kitchen with stove & fridge, a small dining table, a couch, & a comfy queen bed. You control the temperature with your own HVAC system with both heating & cooling. It’s approximately 15 mins to all main universities, the city center & all of the sports arenas.

Cozy King Suite Just off Walnut
In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 1BR/1 bath apartment in a prime location, with all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted & entirely remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances & in-unit laundry is brand new!

Entire home near Kennywood without extra fees.
Bring everyone along for the trip, including Fido! Our home is a cozy, yet spacious Cape Cod southeast of downtown Pittsburgh. The backyard faces a beautiful and peaceful meadow. The yard is fenced in and has a small garden filled with herbs and tomatoes during the summer. Our home has all of the amenities to make your stay enjoyable and easy. We keep our home clean, organized and stocked with essentials. The beds, pillows and sheets are new and comfortable. Parking is plentiful and easy!

Family & Pet-Friendly Home w/ Fenced Yard & Office
Welcome to your ideal Pittsburgh retreat! This fully renovated, pet- and family-friendly home offers comfort and convenience with three bedrooms (including a nursery), a dedicated office with high-speed internet, and a fully equipped kitchen. Family features include baby gates, child-proofed outlets, and a fenced backyard. Located near Kennywood, Sandcastle, and the Waterfront, with easy access to downtown attractions and universities, this house is the perfect base for a relaxing stay.

The Pop Art Studio - Cool, Convenient & Commutable
Conveniently located off of highway 376, tucked away in a Swissvale neighborhood, this newly renovated studio has everything you need for a visit to Pittsburgh. The unique interior design and lovely private patio make our apartment stand out from the rest. Ground floor- no steps required! Parking is free on our street. Enjoy proximity to all Pittsburgh has to offer! Please note, we are in a transitioning neighborhood that's a melting pot of young professionals and longtime residents.

Cheerful 3-bedroom home with on-street parking
Enjoy your stay in this beautifully renovated 3 story 1920s centrally-located home in the Greenfield neighborhood of Pittsburgh (right next to Squirrel Hill). Less than 10 minutes to Downtown, PPG Arena, Bakery Square, CMU, Pitt, Chatham, and Duquesne University. Minutes away from excellent restaurants and bars in Pittsburgh. Fully equipped entire home for an extended or few nights stay. Enjoy outdoor seating on the front porch and back deck with a fenced in backyard.

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.

Pittsburgh Area 2 Bedroom Apt.
Comfortable, Convenient & Clean 2 bedroom apartment (1 queen bed & 1 twin size day bed). Located on a "Pittsburgh Hill" you'll remember in Forest Hills a quiet residential eastern suburb of city. Free off street parking. Downtown & Stadiums 10 mi. Universities, Medical Center, PPG Paints Arena & Carnegie Museums 8 mi. Kennywood Amusement Park, Monroeville Convention Center & Sri Venkateswara Temple 5 mi. I-76 PA Turnpike 8mi. International A/P 27 mi.

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!
Popular amenities for Homestead holiday rentals
Other great holiday rentals in Homestead

Beautiful, Pleasant and Comfortable House

A cozy furnished 1 bedroom lower level Apartment.

Wetroom suite

Penthouse King Suite | Private Balcony | Workspace

Luxury Stay for 12 • Ideal For Families!

The Lee Reynolds House

Cozy apartment in Edgewood

Cozy City Hideaway•Near It All Quiet+ Free Parking
Destinations to explore
- Philadelphia Holiday rentals
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- PNC Park
- Acrisure Stadium
- Fallingwater
- Carnegie Mellon University
- Seven Springs Mountain Resort
- University Of Pittsburgh
- David Lawrence Convention Center
- Ohiopyle State Park
- Pittsburgh Zoo & PPG Aquarium
- Sri Venkateswara Temple
- Idlewild & SoakZone
- Raccoon Creek State Park
- Moraine State Park
- Point State Park
- Phipps Conservatory and Botanical Gardens
- Petersen Events Center
- Schenley Park
- Carnegie Science Center
- National Aviary
- PPG Paints Arena
- Children's Museum of Pittsburgh
- Laurel Hill State Park
- McConnells Mill State Park
- Randyland





