Holiday rentals with a pool in Downtown Pittsburgh

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Top-rated rentals with a pool in Downtown Pittsburgh

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Flat in South Side Flats

4.57 out of 5 average rating, 192 reviews

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.

Home in Carnegie

5 out of 5 average rating, 8 reviews

The Burgh Beach House

Escape to The Burgh Beach House, where you can enjoy relaxing beach vibes, minutes from the heart of the Steel City! This poolside retreat offers the perfect balance of urban connivence and vacation style tranquility. 15 minutes from Downtown Pittsburgh, you'll have easy access to world class dinning, vibrant nightlife, and iconic attractions like PNC Park, Acrisure Stadium, Heinz History center and the Cultural District all while returning to a private poolside oasis! The Burgh Beach House!

Superhost

Flat in Pittsburgh

4.89 out of 5 average rating, 18 reviews

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

Home in Highland Park

4.74 out of 5 average rating, 96 reviews

Eastside Urban Rental

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.

Home in Brookline

4.89 out of 5 average rating, 9 reviews

Family Oasis w/ Heated Pool 7 Min to PGH

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.

Home in Pittsburgh

4.75 out of 5 average rating, 12 reviews

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

Flat in Strip District

New place to stay

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.

Superhost

Home in Coraopolis

5 out of 5 average rating, 37 reviews

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.

Home in Pittsburgh

New place to stay

Posh Pittsburgh

Where elegance meets enchantment—this luxury retreat features a dazzling glass staircase, emerald forest views, a serene pool & spa, high-end appliances, and stylish interior design. Enjoy a marvelous walk-in closet with granite island, luxurious skylit bathrooms, ample parking, and a two-story balcony for elevated living. Crafted with exquisite finishes, this is more than a stay—it’s a rare experience in beauty, comfort, and privacy.

Flat in Strip District

New place to stay

Chic Strip District Retreat

Stylish Strip District Gem Enjoy a stylish experience at this centrally-located place. Spacious 2 bed, 2 bath apartment with open layout and fully equipped kitchen, located in the heart of the Strip District—just minutes from Downtown, Shadyside, and local universities. Enjoy access to a rooftop with stunning river and bridge views, pool, clubhouse, fire pits, and outdoor lounge areas. Modern, chic, and impeccably clean.

Home in West Mifflin

4.86 out of 5 average rating, 7 reviews

3BR retreat w/ Pool(May 30-Sept1) ,Gameroom

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.

Flat in Pittsburgh

4.76 out of 5 average rating, 122 reviews

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.