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2914+ Big Sky Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Big Sky

Discover more than 2914 holiday rentals in Big Sky. PickleTrip™ holiday homes has everything you need to find a place to stay near Big Sky, MT.

Whether you are looking for luxury villas in Big Sky, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place with private pickleball courts or nearby facilities. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Big Sky with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Big Sky for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Big Sky with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Big Sky Holiday Rentals

There are a lot of options in Big Sky. If you plan on staying in the Big Sky area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in Big Sky:

There are many holiday rentals available in Big Sky; however, here are a few of the most popular holiday homes listed in Big Sky on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Big Sky to find one that works for you.
Yes, there are 2914 self-catering family homes and holiday rentals in Big Sky.
There are more than 2914 luxury holiday homes in or near Big Sky, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 2914 pet friendly rentals that are available in Big Sky.