Holiday rentals with a fireplace in Squirrel Hill

Skyline Haven:5BR/3.5BA +2 parking spots + Rooftop

Experience unparalleled luxury in this spacious 5-bedroom, 3.5-bathroom haven, perfectly situated in the heart of Pittsburgh. Boasting not one, but two roof decks, you'll have the finest city vistas right at your fingertips. Relax by the indoor-outdoor gas fireplace this is a serene escape amidst the urban hustle. With the addition of garage parking for 1 vehicle + Parking pad directly in front of the garage door, your downtown retreat combines modern elegance with supreme comfort, promising a m

Peaceful 2BR King Bed Suite | Walk to Walnut St!

Peaceful 2 BR/ 1 bath apartment in the heart of Shadyside! Prime location, steps from UPMC Shadyside & 10 minute walk to Walnut Street! Fully equipped for either a long or short stay! 🌟King/ Queen Bed (Memory foam mattress) ⚡️24/7 Guest support 🌟Pet friendly! ⚡️Central AC/ Heat 🌟Fully stocked & equipped kitchen 🌟Free Street parking ⚡️Laundry (Free & Shared) 🌟Pull out bed ⚡️Minutes away from Pitt & CMU campus! My team and I are here for you before, during and after your stay with us 24/7!

UPSCALE HOME CENTRALLY LOCATED IN SOUTH SIDE FLATS

Centrally located in South Side Flats, many of the most popular S. Side restaurants & bars are a few minutes walk away. The stadiums/arenas are also only a short drive. The home has 1.5 bathrooms & 2 bedrooms (queen bed in each room plus a futon in 2nd BR). Features include air conditioning, 1st floor washer/dryer, private back patio, front porch, & kitchen basics for cooking. I can only register 1 car for parking & it's on-street parking only. There are no assigned spots; 1st come, 1st serve.

"The Cottage on Summit"

The "Cottage on Summit" is charming & updated Historical 1932 Cape Cod, located in the beautiful Bethel Park community. Relax with the whole family in our peaceful, cozy yet spacious home, boasting privacy, comfort and safety, nestled within the Summit neighborhood . NOTE: A "request to book" will need additional information prior to "confirming by the host". Verified ID and at least ONE Positive review & No Negative reviews from previous stays are needed. House rules strictly enforced.

River Ridge Retreat

Discover the charm of our Braddock, PA Airbnb! Just minutes from all Pittsburgh attractions, reach any city hotspot within 20 minutes. Close to Regent Square, Bakery Square, and Point Breeze. Explore Kennywood Park across the river and enjoy quick access to Sandcastle Waterpark. Whether it’s UPMC, downtown, CMU, or The Strip, we’re minutes away from it all! Your perfect Pittsburgh getaway awaits! *If you enjoy this space, the owners are amenable to selling. Please contact for more information

Amazing views! Free Parking!

After a year-long restoration project, we are thrilled to present our home in Pittsburgh's historic north side. What awaits you is a quiet, downtown gem surrounded by nature with amazing city views. What You'll Love: -Total and complete renovation between 2020-2021 -Gourmet, fully-equipped kitchen including coffee/tea station -Remarkable city views -Close to stadiums, downtown, museums -Relaxing patio -Gigabit internet connection -Peaceful nature surroundings -Comfortable memory foam beds

PBR - Pittsburgh Bloomfield Rowhouse

A fully renovated, charming, and comfortable home in the heart of Pittsburgh's Little Italy. Location is just steps away from great dining, shopping, and entertainment. Historic Bloomfield is centrally located in the city and only minutes from local universities, hospitals, and stadiums. This pet friendly 3 bedroom house is perfect for families, friends, and business travelers. Whether you are visiting for work or leisure, this house will make your stay even more delightful. We welcome all!

Sunny, Creative Duplex in Friendship

You and your travel companions will be in an ideal Pgh spot when you stay at this Friendship neighborhood home. With 3 floors, you'll have lots of room to spread out or gather together. This beautifully updated 100-year-old home is a creative space, filled with art from Pgh artists, cheery textiles from around the world, and vintage decor scattered throughout. It’s a charming retreat for artists & writers, a cozy spot for families, or the perfect place for larger groups to share a getaway.

Seneca Place: A historic home in Mount Lebanon.

Seneca Place is a historic home. Our guests have the best of both worlds: a private full residence with attentive and available hosts (right next door). Please note that we charge by guest for requests over two, so please enter the correct number of guests to fully understand your costs. This neighborhood is very quiet with little to no traffic and the hosts are ten feet away. There is a covered side patio with an outdoor sofa as well as a connecting back patio with a fire pit.

Urban converted gas station in heart of South Side

My place is close to art and culture, restaurants and dining, and family-friendly activities. The southside is loaded with bars and restaurants, grocery and clothing stores, galleries, public library and pool. It is very near downtown Pgh and has great bike/running trails along the river. You’ll love my place because of the outdoors space, the neighborhood, the light, the comfy bed, and the kitchen. My place is good for couples, business travelers, and furry friends (pets).

Cozy Entire APT B Friendship Park & Free Parking

Ground Floor Entire apartment with one bedroom, living room, bathroom is located in Bloomfield, a quiet yet vibrant neighborhood that’s central to all the best attractions. It features off Street parking , a rare find in the central city. This space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower. 🎈Smart lock w/ private entrance 🎈Luxurious waterfall shower head 🎈private parking lot 🎈Full equipped kitchen

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!