Why Choose Two Pines?

We're Local

Our neighbors to the right own the local coffee shop and our neighbors to the left own one of the largest local retail shops. When we make recommendations we aren't just sending you to the best, we are sending you to friends.

Family Values

Two Pines Properties takes great pride in the Big Sky community and we love sharing it with others on their vacation. That’s why guests continue to book with Two Pines Properties and consider our rentals their “home-away-from-home." At Two Pines Properties, it’s our goal to make your time in Big Sky an incredible experience. We have a little saying in our company, 'Guests into friends, friends into family.'

Put Down Roots

You finally have your dream home in the mountains. And oh, how sweet it is. But who takes care of your prized possession when you’re away? Who helps you rent it out? And most importantly, who’s offering you the peace of mind you need when sharing your home with others? At Two Pines Properties we are happy to learn about your property care preferences, and would love to partner with you as you share your home in Big Sky with guests!

"Between every two pines is a doorway to a new world."  - John Muir

Here at Two Pines Vacation Rentals we understand what makes a luxury vacation home right for you. We make it our business to find a vacation rental that meets all of your needs and goes above and beyond your expectations. By providing the finest in vacation rentals we can ensure that your vacation is a success no matter where you decide to stay.


When you are staying in Two Pines Vacation Homes it is impossible to be bored. You will find activities and attractions for you and your significant other to your entire family. There will also be many restaurants that will tempt your taste buds. So what are you waiting for, book online today and get out and enjoy a Two Pines Properties Vacation!

Property Management

We know what it takes to run a successful vacation rental management company. Providing quality homes, cleaned by quality employees, and providing quality customer and concierge service is what sets us apart from the rest. Whether you are renting with us or putting your rental in our hands as an owner you can be sure that you working with the best.