Vacation rentals with a pool in Downtown Pittsburgh

1st Fl. Huge Flat on 2 Acres - Pets/Garage Parking

Mediterranean Homestead with vineyard set on 1 acre overlooking Highland Park with Amazing grape arbored patio Sunset view FAST WiFi - PET FRIENDLY - TEMPURPEDIC BED - RAINFALL SHOWER - LAUNDRY - GARAGE PARKING Private Entrance to Huge Open Floor Plan Flat in finished basement of single family home with garage parking 4 min from Target in non-gentrified part of East Liberty/Penn Ave. Bakery Square/Whole Foods/Dinning/Bars/Tennis/Volleyball/Pool/Off Leash Dog Park/Playgrounds/Trails -6 min

20 mins to Downtown- pool table & fenced yard

Only a quick 20 mins to downtown Pittsburgh! Get to PNC Park, Acrisure Stadium, Primanti Bros, Top Golf, and great shopping/eating in minutes. Walk to local grocery, bistro, and the pool (seasonal- ask for info). Vaulted ceilings, granite countertops, lanai, two outdoor fire pits, and fully fenced yard. Two upstairs bedrooms and one basement bedroom all with their own full bathrooms! The basement also has a large dining table that converts to a pool/ping pong table, large TV, and fireplace.

Eastside Vibes ~ Roomy. Peaceful. Charming.

Nestled on a dead-end street in Lincoln, an up & rising URBAN neighborhood, this home is a hidden gem. 1500+ sq. ft of living space. Free on street parking. Ample side yard space. Outdoor above ground 4ft pool w/privacy deck & grill open May-Sep 1st. Not suitable for small children. Very short distance from the East Liberty hot spots! Nearby Pittsburgh's hospitals & universities. 8 miles from Acrisure Stadium & PNC Park. Potential for periodic noise due to trucks accessing a lot next door.

Cozy & Beautiful Pittsburgh Home

We designed this beautifully renovated 2-story home so you can feel at home while visiting Pittsburgh. Comfortable spaces, spacious rooms, lovely wood flooring throughout the home, and more. - 2-10 minutes drive from various UPMC hospitals. 7-20 minute scooter or bike ride. - 7-minute drive to CMU. 14 minute scooter or bike ride. - 5-minute drive to UPitt's Cathedral of Learning. 11 minute scooter or bike ride. - 5-minute drive from the historic South Side and Downtown Pittsburgh

Luxe Lawrenceville Apartment

Chic 800 sq ft luxury apartment in Pittsburgh’s vibrant Strip District & Lawrenceville. Modern open-concept design with hardwood floors and a sleek kitchen. Enjoy a plush queen bed, spa-like bathroom, & in-unit laundry. Dog-friendly building with a top-tier gym & 24/7 concierge. Steps from top restaurants, bars, & nightlife, plus markets & riverfront trails. Perfect for couples or solo travelers seeking a stylish, pet-friendly retreat in the heart of the city’s social scene.

PIT Staycation Retreat with Pool House!

This property was designed for guests to make unforgettable memories with loved ones. Unwind with a memorable Staycation at this newly renovated oasis that comfortably entertains up to 6 adults + children under 12. Prime location just off I-79 is a close to PIT airport, PIT stadiums, RMU, Riverhounds' facility, hospitals, downtown & tons of shopping/dining. To maintain a quiet neighborhood, we respect “no party” and “quiet hours” rules with zero tolerance.

Playing Hooky

Want to get lost on a country road that is still close to town, Come vist Playing Hooky, a country dirt road and a secluded acre lot teeming with perennial flora, this 3 bedroom 2 bathroom home will delight all who enter. Highlights include a hot tub, above ground swimming pool, a 3 bay garage with loft above. Close proximity to Pittsburgh Field Club, Oakmont Golf course and a twenty minute drive to downtown Pittsburgh.

3BR Home w/ Pool, Deck, Scenery, near Pittsburgh

Enjoy the perfect family getaway in this centrally located, fun-filled retreat! Just minutes from top attractions—amusement parks, restaurants, cafes, a movie theater, and family-friendly entertainment—you’ll never run out of things to do. When it’s time to unwind, relax at home with your own private above-ground pool or challenge each other to a game of pool in the lower level game room! No locals please.

CozySuites | Lavish SDO, Lawrenceville

CozySuites proudly brings you our newest Condos in Pittsburgh. Located in the heart of Lawrenceville and convenient to all the chic dining and drinking options in town, this condo is perfect for leisure and business travelers! Like all CozySuites, this condo feature seamless check-in, fast wifi, thoughtful touches, and a tech-first approach – so you can live like a local and feel at home on the road.