As of March 2, 2020, there are five contests offering chances to win a free trip to Hawaii. Enter these Hawaii sweepstakes now and perhaps you’ll be one of the lucky people vacationing in the islands for free. Enter today, before it’s too late!
Who doesn’t want a free trip to Hawaii? Cheap flights to Hawaii can’t even touch winning the ultimate Hawaii sweepstakes.
Beat of Hawaii has no affiliation with any of these sweepstakes including who wins. Have fun and let us know if you’re entering, and especially if you are the next lucky winner! It’s happened before where one of our Beat of Hawaii readers had the winning entry.
As a reminder, read all the rules, since each contest is quite different. While some of these include other prizes, we have only listed the free Hawaii vacations.
How to enter. Click on the title of each sweepstakes/contest below to visit contest sites and complete entry forms. No purchase needed. Also be sure to uncheck any applicable boxes if you don’t want to receive other emails from contest sponsors.
Tip. Some readers have said they use a separate email address for entering to win a free trip to Hawaii. That way they can avoid potential spam in their regular mailbox.
March Win A Free Trip to Hawaii Sweepstakes
Hawaii prize: Ten monthly trips for two to Hawaii (or other location of choice). Includes $1,000 airfare, accommodations, plus $100.
Enter by: October 5, 2020.
Open to: Legal residents of U.S. (except ID, NE, NJ, PR, WV) age 21 and over.
Note: Hawaii is not the grand prize in this sweepstakes but rather one of multiple secondary prizes.
Grand prize: Eight day trip for two to Maui. Includes airfare and accommodations.
Enter by: May 25, 2020.
Open to: US and Canada (except Quebec) residents, age of majority.
Disney on Ice/Hawaiian Airlines Sweepstakes
Grand prize: 240,000 HawaiianMiles from Hawaiian Airlines. Mainland round trip awards start at 35,000 Miles, so up to 6 round trips are possible.
Enter by: March 20, 2020.
Open to: Legal residents of contiguous U.S. age 18 and over.
Hardwood to Hawaii Sweepstakes
Grand prize: Four day trip for two to Oahu. Includes airfare and accommodations.
Enter by: June 30, 2020.
Open to: Legal residents of California whose primary residence is within a 150 mile radius of LA.
Grand prize: Eleven day trip for two to Maui. Includes airfare and accommodations.
Enter by: July 31, 2020.
Open to: Residents of the US and Canada (except Quebec) age 21 and over.
Updated March 2, 2020.
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Ken S. says
We have celebrated our 40th wedding anniversary. My wife has never been to Hawaii . But she has always dreamed of going. This would be a thrill for both of us. Aloha
Beat of Hawaii says
Hi Ken.
Good luck.
Aloha.
Jessica L. says
Flying from sf to Maui hopefully 🤗
Daniel F. says
I do deserve this 😍
Victor O. says
Please enter me in the free trip to Hawaii contest. Thank you.
Beat of Hawaii says
Hi Victor.
You need to enter these contests yourself if you are interested. Follow the links.
Aloha.
Mary E. says
Beware of Diamond Resorts Sweeps. Entered a while ago & immediately rec’d a phone call from them. Believe them to be a timeshare outfit.
Jade S. says
my partner and i have never taken a trip together yet. this would be the perfect opportunity.
deb h says
dream of a lifetime!
John G. says
This trip would be paradise beyond belief!
Dorrie C. says
Looking to live on island, preferably Kona. Retiring soon, and love the Aloha life !! Mahalo
Sydney S says
Traveling from Syracuse, Ny!! Really need to get away from life at home. This would be the best thing that’s ever happened for me.
Paulette H says
Would be a bountiful blessing to FLY
From Los. Angeles, CA to Hilo, HI for my 55th birthday in April, 2020
Peace, Love and Light and THANK YOU!!!
Tanya H. says
Flying from Ftlauderdale Florida! would love this package! we get married 2/13/2021
Krystal C says
Thanks for creating this! I’d love to go back and see my family!! 💙🤙🏼
Sylvia T. says
We are celebrating our 50th wedding anniversary in April. That would be the best present ever to go back to Hawaii. We love Maui,and all the islands. Mahalo and thank-you.
Beat of Hawaii says
Good luck Sylvia!
Aloha.