1. Hawaii
  2. Kihei
  3. Wailea
  4. Ski Chalets

Wailea Ski Chalets Rentals & Holiday Homes

Find the best ski chalets in Wailea - We found 1850 exact matches

About Wailea Ski Chalets on Hawaii.Villas

Ski-chalets are a popular choice in Wailea. At HawaiiVillas, we offer more than 1850 ski chalets near Wailea to suit your budget and preferences. These chalets are a great option for those looking for a place to stay while enjoying their skiing and snowboarding adventures in the winter, or hiking in the summer. HawaiiVillas vacation homes are perfect for families, groups, friends, or wedding retreats, and they come with great amenities.

HawaiiVillas offers several luxury chalets to those who love outdoor travel experiences. The site provides dog-friendly & self-catering ski chalet rentals near Wailea, so you can take on all of your adventures with ease, then come back to your rental for more pleasure and comfort.

If you love chalet skiing with patio options or private chalets, there are more than 1850 of them available near Wailea. Some examples of these chalets include romantic chalets, mountain chalets, catered ski chalets, and self-catering ski chalets. Your vacation gets better as you book your holiday chalet with HawaiiVillas for your next trip.

HawaiiVillas has a large list of Airbnb, VRBO, HawaiiVillas-style ski chalets, holiday rentals, and vacation homes that could be the perfect option for your next trip. Get ready for your next getaway by booking a top-rated chalet in Wailea with views of the beautiful scenery & the best activities to engage with. So whether you are looking for a romantic place for the weekend, a spacious chalet for your family or friends, or something for yourself alone, you are one click away from getting all these on HawaiiVillas.

Show more
Show less

Ski Chalets: Explore Top Destinations

Explore More

Frequently Asked Questions About Wailea Rental Ski Chalets

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

There are many ski chalets available in Wailea; however, here are the most popular ski chalets listed in Wailea:
Hawaii.Villas offers availability throughout the year, but you can book pre-Christmas, mid-January, or before and after the school break at Easter are the best times for renting in Wailea.
At Hawaii.Villas most of our ski chalets are perfect for families. Check out the complete list of ski chalets in Wailea to find what works for you.
Yes, there are 1850 self-catering family ski chalet in Wailea that have hot tubs & other amenities.
There are more than 1850 luxury ski chalets for families or group in or near Wailea, with other amenities available according to data 2026 from Hawaii.Villas.
Yes, there are more than 1850 pet friendly ski chalets that are available in Wailea.
We have a list of top-rated ski chalets for families to stay at Christmas or New Year's holiday near Wailea.