Holiday rentals with a pool in Pittsburgh

Charming Pittsburgh Getaway - Private Home- 2 Beds

This charming Tudor style house is your next oasis. Private entrance to the entire 2nd floor unit with a brand new kitchen, dining room, and two bedrooms one of which has a dedicated workspace. Private courtyard with a fire pit. 2 blocks from the T Dormont Junction train station. Take the T into the city to catch a Pirates, Steelers, or Penguins game. Walking distance to the restaurants and shops on Beverly Road and Washington Rd. Free street parking. Dormont pool passes sold at pool Jun-Aug.

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!

Mayberry Escape

Discover the charm of this inviting 3-bed, 3.5-bath Monroeville home! Immerse yourself in luxury with a heated pool (seasonal), rejuvenating infrared sauna, expansive decks, a private backyard, a fully equipped kitchen, a finished basement, and a delightful fire pit overlooking the pool. Experience comfort and style with off-street parking included. Enquire now to make this your own sanctuary! ***If you enjoy this space, the owners are amenable to selling. Please contact for more information***

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.

Urban Pittsburgh Home w/ Pool

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 Home in Pgh area Pool OPEN, Sleeps up to 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.

Stay & Relax in our Cozy 4bd 3ba w/Pool in Plum PA

We are glad to share our beautiful 3 bedroom plus den w/trundle bed, 3 baths & finished basement home that has been tastefully renovated & furnished. We have a beautiful pool and outside deck along with a fire table to sit and relax with a glass of wine after a nice meal on the BBQ grill. Our home is the only AirB&B in Holiday Park and we chose it for its location peacefulness and tranquility. Go ahead and stay with us, you will return home fresh and energized.

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.

Heated Pool Oasis • Free Parking • 5 min to PGH

Family- & pet-friendly 4BR/2BA designer home featuring original artwork, a private pool, crib, high chair, baby play station & fenced yard. Senior-friendly split level with very few stairs. Just minutes to downtown, stadiums, and museums, 5 mins to Mt. Washington, 10 mins to Oakland & the Strip District, 15 mins to Lawrenceville & SouthSide Works. Enjoy open living and a stylish, senior-friendly space. Perfect for families, sports fans, and city explorers.

Rooftop Deck | Perfect for Entertaining | Upscale!

Soak up jaw-dropping skyline views from four private outdoor spaces—including a full rooftop deck with grill, fire pit, bar seating & games. Perfect for families and groups, this 5-floor South Side Slopes retreat features a game-packed basement (ping pong, pool, darts), luxe primary suite (with city views!), spacious living areas, garage parking, and even a massage-chair “man cave.” The ultimate Pittsburgh stay for gathering, relaxing & making memories.

CMU Graduation Oasis

Architect-designed eco-luxe studio retreat perfect for your NFL Draft stay. This modern net-zero space features soaring windows, and a flexible open layout. Unwind in your private backyard oasis with a heated pool, waterfall, fire pit, jacuzzi tub and outdoor lounge. Walk to CMU, Pitt, museums, and parks, with quick access to downtown Draft events. A serene, design-forward escape just minutes from the action. This unique place has a style all its own.