March Contests | Win a Free Trip to Hawaii Sweepstakes

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

Diamond Resorts 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.

Rise to Maui Sweepstakes 

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.

Miraclesuit Maui Sweepstakes 

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.