FLEXIBLE CANCELLATION POLICY on all bookings between June 1st - December 1st. Details here

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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!


*** The health and safety of our community and Two Pines guests is paramount. We are closely monitoring Coronavirus COVID-19 and related guidance from the CDC to ensure the highest health and safety standards are met for Two Pines Properties guests.***

Voted Best Property Management Company and Second-Best Overall Business in Big Sky!

Two Pines Properties is very excited to announce our awards for this year's 'Best of Big Sky!' We work tirelessly to deliver the best possible customer service and value to our guests. Our goal has always been to do business the right way while positively impacting the wonderful community that is Big Sky!

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

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 in Big Sky 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. 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 you can be sure that you working with the best.