Holiday rentals with a pool in Pittsburgh

Top Guest favourite

Guest favourite

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.

Location · Family · Decor

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***

Family · Location · Bathroom

Posh Pittsburgh: art deco wellness sanctuary

Where elegance meets enchantment—this luxury abode features a dazzling glass staircase, emerald forest views, a serene pool & spa, high-end appliances, and feng shui design. Feel like a celebrity here where A-listers filmed scenes from the movie, Adventureland. Hello, Superstar! *Customizable retreat planning available: we partner with The Root Camp Experience to provide on-site and/or off-site wellness amenities.* This is more than a stay—it is a rare experience in comfort and exclusivity.

Family · Location · Hospitality

Top Guest favourite

Guest favourite

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.

Family · Location · Indoor spaces

Charming Urban Pittsburgh Retreat!

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.

Value · Family · Backyard

FIDO PLUS TWO 1.5 miles to Acrisure Stadium

Our cozy first-floor apartment is a unique space designed with you and your dog in mind. Sometimes Fido needs a vacation too and our home has every essential for all of your comfort. Come experience the vibe of Pittsburgh’s North Side! We are less than ten minutes from Downtown and 2 miles from Acrisure Stadium. You will be centrally located near all that Pittsburgh has to offer. The Cultural District, the Business District, and iconic Andy Warhol are all within a 5-mile radius.

Value · Comfort · Getting around

Top Guest favourite

Guest favourite

Cozy Home in Pgh area, 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.

Location · Family · Comfort

Top Guest favourite

Guest favourite

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.

Value · Family · Laundry

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.

Location · Family · Accuracy

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.

Heated Pool Oasis • Free Parking • 5 min to PGH

Family- & pet-friendly 4BR/2BA designer home with original artwork, private pool, crib, high chair, baby play station & fenced yard. Senior-friendly split level with few stairs. Minutes to downtown, stadiums & museums, 5 mins to Mt. Washington, 10 mins to Oakland & the Strip District, 15 mins to Lawrenceville & SouthSide Works. Two living rooms let kids and parents enjoy separate spaces. Perfect for families, sports fans & city explorers.

Family · Location · Nearby

Resort Style Living in the heart of Pittsburgh!

The perfect combination of luxury, location, and entertainment in the heart of Pittsburgh’s vibrant Strip District. Step outside the back door and find restaurants, nightlife, clubs, shopping, and entertainment just moments away. You’ll also be incredibly close to Pittsburgh’s biggest attractions! Enjoy the energy of the city right outside your door and the comfort of an upscale retreat when you return.

Location · Bathroom · Kitchen