House holiday rentals in Oakmont

4.96 out of 5 average rating, 111 reviews

Home in Sewickley

Hydrangea Cottage in Sewickley Village 4bd/1.5 b

Dates not available? Check out our listing across the street, Boxwood House in Sewickley | Hot Tub | 3bd/1.5ba. Welcome to Hydrangea Cottage, a charming 4 bedroom carriage house on a quiet, residential lane in the heart of Sewickley Village. This cozy, private home sleeps 5 to 7 comfortably, is stocked with everything you need to relax, is a 5 min walk to local shops and restaurants, & a 20 min drive to Steelers & Pens stadiums. Downtown Pittsburgh: 20 min drive PIT Intl Airport: 15 min drive

4.97 out of 5 average rating, 186 reviews

Home in South Side Flats

Pittsburgh's Tropicana w/ outdoor hot tub

Family owned and managed, immaculate high end, tropical inspired home located on the historic Southside. Only 3 blocks from Carson Street Close to downtown (2.8 miles) universities, sport/concert venues(3.9 miles) Keep your cars safely parked in our huge driveway with security camera! No need to drive around looking for spaces! Fantastic outdoor area with grill and jacuzzi! It's like you are in your own private little resort *Check out our other 5 star house Gorgeous Southside Slopes House*

4.94 out of 5 average rating, 167 reviews

Huge 6 BDRM min to Downtown & Stadiums w/ parking

Gather with friends and family in our renovated Pittsburgh home, designed for comfort and fun! ✅ 6 Large Bedrooms & 3 Full Baths – Includes a soaking tub ✅ Easy Parking – Two-car driveway + plenty of free street parking ✅ Stocked Kitchen – Fully equipped with essentials ✅ Spacious Living Areas – Two living rooms for lounging ✅ Entertainment – Projector & sound system for movie nights ✅ Family & Pet-Friendly – Room for everyone ✅ Cozy Fireplace – Available Nov.–Feb. Everyone will enjoy it!

Superhost

Home in Murrysville

4.89 out of 5 average rating, 125 reviews

Gorgeous Modernized Cabin + Hot Tub + Pool Table

Welcome to this incredible, fully renovated true log home with a massive entertainment room consisting of a pool table, ping pong table and more 🔥 3 full sized bedrooms along with an additional room with a pull out couch. There are 3 private bedrooms or use it as 4 with a wall separation. Fully equipped kitchen with quartz countertops and stainless appliances. Large front porch with plenty of furnishings and a rear deck with a view of a farm. Huge 2 car garage for parking and a driveway! 🚘

4.99 out of 5 average rating, 105 reviews

Home in Sarver

Country Retreat: Indoor Pool/Pickle Ball/Sleeps 12

Our home is over 3500 square feet located on a 21 acre parcel. If you are looking for a quiet, private location, this is it! The home is nestled in the back of a pasture flanked by wooded areas on both sides and a barn located near the front entrance. The property includes plenty of outdoor parking. Hard to justify with any one photo however it is very spacious and includes an attached indoor heated pool and a new Pickle Ball/Sport court. A charming, picturesque place for all to enjoy.

4.97 out of 5 average rating, 403 reviews

Head to Pittsburgh From Mt. Lebanon Cottage

Mt. Lebanon Cottage is a craftsman-style home that fuses contemporary styles with traditional elements. Enjoy our well-equipped kitchen, enjoy a coffee for two on the deck nestled in the trees or unwind on the front porch and enjoy the friendly neighborhood vibe. The home is in a walkable neighborhood of tree-lined streets and friendly locals. Blocks from unique shopping boutique options and dine at tasty local restaurants. Hike in the nearby nature and visit Pittsburgh just minutes away.

5 out of 5 average rating, 223 reviews

Home in South Side Flats

High-End South Side 4 Bedroom House, sleeps 15!

Newly Remodeled, Gorgeous High-End 4 Bedroom, 3 Full Bathroom entire house in the heart of Pittsburgh's historic South Side neighborhood; SLEEPS UP TO 15 PEOPLE; Pets welcome; Private/Enclosed Patio Hardwood floors, raised tin ceilings on first floor; open floor plan living room/kitchen with stainless-steel appliances, marble-counter-tops, Keurig, 70 inch TV, WiFi, Convenient 2nd floor laundry facilities,HD Televisions in every bedroom w/ Cable, Luxurious Memory Foam Beds

4.86 out of 5 average rating, 130 reviews

100% renovated House 8 minutes to downtown

This is a renovated and conveniently located just a 10 minute drive from downtown! Enjoy hassle-free check-in as you make your way down the stairway to the porch and enter into the welcoming kitchen. With all new appliances, enjoy cooking up meals in the modern kitchen or rest in the living room, every space has been fully updated for the utmost comfortability. The bathroom is one of the highlights with its beautiful updates and amenities. Street parking. Must do steps!!

4.96 out of 5 average rating, 102 reviews

Home in Conway

Charming Renovated Home

This centrally located house is close to the communities of Cranberry Township, Pittsburgh, and Sewickley. Our home has been completely renovated from top to bottom and is pristine condition. An open concept design is offered on the main level connecting the dining room, living room, and fully equipped kitchen. Also on the main level is a half bath for your convenience. Upstairs you will discover a full bath and 2 cozy bedrooms with beautiful vaulted beamed ceilings.

4.97 out of 5 average rating, 193 reviews

Home in Sewickley

The Sewickley House: Historic Charm-Modern Comfort

The Sewickley House is a charming, completely remodeled house located in the heart of Sewickley's historic district - a short walk to the Village of Sewickley with unique shops and restaurants. Located on a quiet and quaint street, you can relax on the front porch swing or enjoy the private back patio during your visit. With modern amenities and a focus on comfort, this house is a destination or enjoy the city attractions with a 20 minute drive to downtown Pittsburgh.

4.99 out of 5 average rating, 149 reviews

The Larrybird Inn - Steps from Butler Street!

The Larrybird Inn is situated in the heart of Lawrenceville, in a beautifully restored home over 100 years old. Park your car for the weekend and enjoy the neighborhood and other surrounding areas by foot or bike. Walk to nearby bars, restaurants, see a movie all within hundreds of feet away! There is also Arsenal bowling lanes across the street! We invite you to stay in our home, one of the most charming Airbnbs in Lawrenceville.