Holiday rentals with a pool in Downtown 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!

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!

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.

*Posh Pittsburgh* 2-story suite w/ pool & hot tub

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

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.

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.

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.

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.