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“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” — Mark Twain

Recognition and Awards


Wherever Your Dreams May Take You

What Our Customers Are Saying

  • I would love to return someday and thank you again Private Trade Winds for the recommendation and all the little touches that make working with you such a pleasure.
    David K.
  • Happy Family With Two Children Playing In A Swimming PoolWe are already trying to figure out how and when to go back. Thanks for everything!
  • Worked perfectly for our three couples. We would all rent from Private Trade Winds again. The attention to detail was perfect, down to the basket of “Items that may have been left behind.”
    Kathy P.
  • Ziplining_HualalaiI would not only highly recommend but I can see coming back and renting again directly through Private Trade Winds.
    Ms. Pesuric
  • I was very satisfied with the villa and felt it was accurately depicted in the listing. Views were tremendous; location superb. Looking forward to our next visit at a similar property.
    Brandon S.

Here’s What the Kid’s Say

  • girl1We were certainly in the lap of luxury and enjoyed every minute we were there. I asked my eight-year-old how she liked her first villa vacation while we were on our flight home, and she said, “I feel like it was a great blessing to stay in such a beautiful place. It made me feel closer to my family.” You can’t ask for more than that from a vacation. We created memories that will last a lifetime. With most vacations, we are usually ready to head home as we near the end of our stay, but this one was different – nobody wanted to leave!
    Greg C
  • Hugo and Friends Group BoatCabo was such a fun trip for surfing and fishing.  I’m glad we stayed in a condo so all my family and friends could be together!  I can’t wait to do it again.
    Robert C.
    Age 15
  • Hugo and Friends GolfI like to golf, surf and play volleyball which I can do even on vacation.  I’ve enjoyed travelling to Pebble Beach, Hawaii, and Cabo with my favorite friends plus we can play video games in the living room till late at night while our parents enjoy cooking dinner.
    David L.
    Age 14
  • Italy was the most amazing trip I have ever been on!  From touring the cities to sunbathing in the vineyards and on Lake Como, only the food and shopping were an equal match.  My favorite memory of Tuscany was having an outdoor dinner on our patio (all 17 of us!)  overlooking the rolling hills and listening to Andre Bochelli.  Well, at least all the moms and daughters were in heaven!
    Ariana K.
    Age 18
  • DSC00086

    I am blessed to have traveled with my best friend since I was 4 months old!  Our families always share a house or get two condos so we can all stay close and enjoy each moment of our trips.  We have been to beaches around the world and enjoyed the snow on several mountains.  Each with its distinct memories.  Italy was one of the best because 4 families traveled together through Tuscany and Lake Como was an adventure but staying in a Tuscany villa was the best!

    Katarina C.
    Age 17