Updated as of October 1, 2019. Enter Hawaii sweepstakes for a chance to win a free trip to Hawaii. New contests include a Hawaii cruise, plus $50,000 in cash. Enter these Hawaii sweepstakes now for a chance to be one of the many lucky people who will be vacationing in the islands for free.
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.
October Win A Free Trip to Hawaii Sweepstakes
Grand and other prizes: 1) Trip to Hawaii in the form of 250,000 HawaiianMiles from Hawaiian Airlines plus a $3,000 cruise vacation voucher. The miles are enough for 4-6 round trips from the west coast to any Hawaiian Island. 2) Trip to Hawaii in the form of 100,000 HawaiianMiles. 3) Trip to Hawaii in the form of 50,000 HawaiianMiles.
Enter by: November 30, 2019.
Open to: Legal residents of the US age 21 and over.
Grand prize: Trip to Hawaii (or Bali or Belize). Includes $3,750 in the form of gift cards plus trip expedition trip.
Enter by: October 10, 2019.
Open to: Legal residents of the US (except Rhode Island) age 18 and over.
Grand prize: Trip for two to Hawaii in the form of 120,000 HawaiianMiles from Hawaiian Airlines. That’s enough for 2-3 round trips from the west coast to any Hawaiian island.
Enter by: October 31, 2019.
Open to: Legal residents of Alameda, Contra Costa, Lake, Marin, Mendocino, Napa, San Francisco, San Mateo, Santa Clara, Solano and Sonoma counties.
Grand prize: Trip for two to Maui. Includes airfare and accommodations.
Enter by: November 15, 2019.
Open to: Age 16 and over.
Grand prize: Nine day trip for two to Hawaii. Includes airfare to Honolulu, 7-night Hawaiian Islands cruise.
Enter by: October 31, 2019.
Open to: Legal residents of the US age 55 and over.
Grand prize: $50,000. This is a Hawaii themed contest paying cash.
Enter by: October 22, 2019.
Open to: Legal residents of the US and Canada (except Quebec) age 18 and over.
Grand prize: Six day trip for two to Maui. Includes airfare, condo, car.
Enter by: January 31, 2020
Open to: Residents of the US and Canada (except Quebec) age 21 and over.
Updated October 1, 2019.