Vacation rentals with a pool in Downtown Pittsburgh

Kasa | Family 2BD with Gym & Sauna | SoSide Flats

Stay in the vibrant South Side Flats neighborhood, just 10 minutes from PNC Park and 15 minutes from Acrisure Stadium and the Carnegie Museum of Art. Enjoy amenities like an indoor pool, outdoor grill, hot tub, and sauna. Explore nearby nightlife, cozy pubs, and unique shops. Want to venture out? Take a stroll along the walking and biking trails by the Monongahela River. Kasa’s tech-enabled apartments offer self check-in at 4pm and 24/7 guest support via text or phone, plus a Virtual Front Desk.

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

A beautiful cozy home away from home!

Bring the whole family to this newly remodeled cozy home with lots of room for fun. Located in a quite neighborhood in Penn Hills. 6 miles to Monroeville, 16 mills to Downtown Pittsburgh and 15 miles to Acrisure and PNC Park! 1 King bedroom 1 Queen bedroom 1 Full bedroom 1 set of bunk beds in the play room (bottom bunk is a double bed) 1 Private driveway Beatiful equipped Kitchen washer/dryer WI-FI There is a full apartment downstairs of the home. It is fully occupied and not accessible!

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.

City-Edge Comfort • 4BR• Garage + Driveway

Welcome to Your Pittsburgh Getaway – Family & Pet-Friendly with Pool! Family- & pet-friendly 4BR/2BA luxury home with a private pool, crib, and fenced yard. Senior friendly split level with very few stairs. Just 7 mins to downtown, stadiums, and museums, 5 mins to Mt. Washington, 10 mins to Oakland & the Strip District, 15 mins to Lawrenceville & SouthSide Works. Enjoy curated artwork, open living, and a stylish, senior-friendly space. Perfect for families, sports fans, and city explorer.

Posh Pittsburgh ~ 2-story luxury suite & patio

Where elegance meets enchantment—this luxury retreat features a dazzling glass staircase, emerald forest views, a serene pool & spa, high-end appliances, and feng shui interior design. Enjoy a marvelous walk-in closet with granite island, luxurious skylit bathrooms, ample parking, and a two-story balcony for elevated living. Feel like a celebrity here where A-listers filmed scenes from the movie, Adventureland. This is more than a stay—it’s a rare experience in comfort and exclusivity.

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

4BR Victorian House in Shadyside Off of Walnut St

IF BOOKING FOR THE NFL DRAFT DATES, INQUIRE ABOUT PRIVATE POOL, 6 PERSON HOT TUB, SAUNA, INDOOR BASKETBALL HALF COURT and SECOND HOME NEXT DOOR. A large Victorian home is in the Shadyside area of Pittsburgh. The home is just steps away from some of the best shopping! There is an Apple Store, Gap, a mom and pop toy store, bars and so much more! The location is also very nice for a short trip to Oakland, Lawrenceville, Downtown Pittsburgh and stores like Target and Whole Foods.

3BR, 2 Bath Home -Pool, Deck, near Pgh, Sleeps 10

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. Air mattress available for 2 additional guests in Gameroom. No locals.

Cozy Steel City 1 Bedroom

Kick back and relax in this calm and stylish space. Equal parts comfy and charming, this apartment is located in the quaint Pittsburgh neighborhood of Brookline which is 8 minutes southwest of the center of downtown. A 5 minute walk will have you on Brooklines main street including restaurants and bars. This spot is perfect for a couples weekend getaway, the lone traveller on business or extended work trips. We look forward to hosting you in the Steel City!

Oasis on the edge

Escape the hustle and bustle of downtown Pittsburgh and step into your own secluded retreat. Nestled just fifteen minutes from the city center, Oasis on the Edge offers the perfect blend of urban convenience and peaceful seclusion. Set on four and a half acres of lush greenery, our property feels like a private park, complete with scenic trails and a vibrant garden that invites you to unwind. Relax in this spacious and serene space.

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.