Holiday rentals with a hot tub in Pittsburgh

Secluded Hilltop Hideaway~Hot Tub~Two Living Rooms

A peaceful escape close to the city. Nestled in a private wooded setting, this 4BR home is just 15 minutes from downtown Pittsburgh. Relax on a wrap-around balcony, unwind in the hot tub, or gather for conversation around the fire pit under the trees. With space for families, pets, and friends, plus trails just steps away, it’s a perfect blend of natural privacy and city convenience. The inside offers a refined treehouse vibe - with warm, modern interiors surrounded by serene woodland views.

Gorgeous Southside slopes house w/outdoor hot tub

This family owned and managed, immaculate one of kind custom home overlooks the entire city from Mt Washington, downtown to Oakland and beyond. Enjoy a coffee/cocktail on the master bedroom balcony! Our outdoor areas are perfect for entertaining and BBQ's. Year round outdoor hottub Private driveway with security camera to park your cars, no more driving around looking for parking on city streets! 4.8 miles to Arenas 2.8 miles to Oakland Check out our other high end house "Pittsburgh’s Tropicana"

Urban Oasis Home - Hot Tub, Pet-friendly, Koi Pond

This charming historical home is close to everything! You can be downtown within 5 minutes. You'll be minutes from the stadiums, museums, and the casino! Pamper yourself. Relax in the hot tub while listening to the sounds of the waterfall over the pond. Watch the colorful Koi splash and play. The meticulously landscaped grounds have countless surprises and beauty in every season. You will enjoy every comfort in this luxurious three-bedroom and 2.5 baths. There's even a shower for your furbaby!

Hot tub | BBQ | Fire pit | Garage | Near Downtown

Minutes from Pittsburgh’s best: -3 min to Strip District -6 min to CMU & Pitt -7 min to Lawrenceville -9 min to Downtown (PPG Arena) -12 min to Northside (PNC Park) Unwind with these amenities: ✓ BBQ grill + hibachi setup ✓ Backyard fire pit for marshmallow roasting ✓ Bug-free outdoor dining tent ✓ Indoor jetted whirlpool hot tub for 2 ✓ Private bathroom — no sharing unless it’s your partner ✓ One-car parking garage, plenty other street parking Perfect if you want city access and privacy.

Steep Retreat Hazelwood Greenway

Take it easy at this unique retreat where the city and greenway meet. This 2 BD/ 1.5 BA home, built during the depression and renovated during the pandemic, boasts of these eras. It is located in the mid heights of Hazelwood just below the cemetery on a dead end street. It requires a 42 step ascent to the entrance. It has more decks than bedrooms and a hot tub that shares the lower deck with a propane grill. Nearby: Waterfront, Southside, Squirrel Hill, the City Parks and the GAP trail.

HotTub | FirePit | Outdoor Theater | Games| 5 Star

Feel like you’re on top of the world in our freshly renovated 3-level home situated on a hill overlooking the Pittsburgh skyline, Allegheny River and Sixteenth Street Bridge. The two decks offer breathtaking city views while you sip your morning coffee or evening cocktail. Located in the historic and emerging neighborhood of Troy Hill, you're just a 5-minute drive from downtown, major attractions, and the Strip District. Our house is the ideal starting point for your next adventure.

Mountain Retreat in the Heart of the City

Brand new home in one of the city's most desirable neighborhoods overlooking Pittsburgh's iconic skyline. This host proudly boasts a number of unique amenities such as 3 deluxe full bathrooms with custom showers, professional cook series kitchen with wine bar, stamped concrete patio with hot tub for 6, outdoor natural gas fire pit and indoor electric fireplace, Wi Fi, bluetooth technology, over 4000 channels including pay per view, all sports and new release movies and tv series.

Hot tub & renovated house 9 minutes from downtown!

Experience the calm and convenience of this house situated a few minutes away from Pittsburgh's most spectacular views. Park with ease in the private driveway and parking pad. Step inside to find a spacious living room, dining room and kitchen. Take the stairs or to explore the upper level bathroom, 2 bedrooms with King & Full beds. The additional King bedroom is in the basement. Enjoy a stress-free stay with no cleaning required and no smoking. NO chores for checkout!!

Hot Tub, King Bed, Cabin Vibes in Lawrenceville!

With cozy cabin vibes, exposed brick, and designer touches, this romantic getaway is perfect for couples or a relaxing stay. Escape to a rustic-modern retreat in the heart of Lawrenceville, just one block from Butler Street! Unwind in the private hot tub, snuggle up on the couch by the fireplace, or explore the city's best dining and nightlife just steps away. Completely remodeled in January 2025 with luxe amenities—book now for an unforgettable stay!

"The Spa Room" Renovated Flashlight Factory

Beautiful 1700 sq ft loft apartment. Located in historic north side. Minutes from both the stadiums, night life, casino, and museums! Best suited for 2 but can accommodate 4. Hard wood floors. Exposed brick. Huge state of the art kitchen. Beautifully executed bathroom with a walk in shower and massive soaking tub. If the bathtub isn't enough for you there is a hot tub located in the light well 1 floor down from the loft. Our other AirB&B is a Plus.

HotTub/Firepit/Parking! Less than 1mi PNC Park

This hip, urban, north-side property is all about location and fun. Private Parking and so close to everything! Check out the outdoor Space! Sports, Museums, Casinos. From hipster to upscale, there's plenty to explore. Colleges? Premier medical facilities? Tech jobs? Yeah, we got those, too. Book this hip haven & immerse yourself in city life. Live like a local from a home that's as cool as the city itself. Private Parking!

Boxwood House | Sewickley Retreat + Hot Tub

Welcome to Boxwood House, your stylish retreat in Sewickley Village, one of Pittsburgh’s most charming neighborhoods. This fully private 3BR home features an inviting hot tub, cozy fire pit, and designer details throughout. Walk to cafés, shops, and restaurants, or unwind in the backyard after a day in the city - located two blocks from Sewickley Village and just 20 minutes to downtown and 15 minutes to PIT Airport.