New Contests | Win a Free Trip to Hawaii Sweepstakes

Updated as of October 17, 2019 with new contests. Enter Hawaii sweepstakes for a chance to win a free trip to Hawaii. 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.

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.

October Win A Free Trip to Hawaii Sweepstakes

Mineragua Holidays in Hawaii Sweepstakes (New)

Grand prize: Trip for two to Oahu in the form of $2000 resort gift card for accommodations at the Turtle Bay Resort, $1800 airline gift card, $600 Visa gift card.
Enter by: November 17, 2019.
Open to: Legal residents of of the US age 18 and over.

Outrigger What’s Your Waikiki Sweepstakes (New)

Grand prize: Trip for two to Oahu. Includes 120,000 HawaiianMiles from Hawaiian Airlines plus five nights accommodations at a choice of Outrigger hotels. The miles are enough for 2-3 round trips from the west coast to any Hawaiian Island
Enter by: November 25, 2019.
Open to: Legal residents of the US age 18 and over.

Win a Trip to Billabong Pipemasters (New)

Grand prize: Trip for two to Oahu. Includes airfare plus three nights accommodation. Must be used to attend the 2019 Billabong Pipe Masters event in Oahu, which starts December 8, 2019.
Enter by: October 31, 2019.
Open to: Legal residents of the US (except Rhode Island) age 18 and over.

HawaiianMiles & Dream Cruise Giveaway

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.

Aloha Fridays Sweepstakes (Northern California residents)

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.

Omaze Win a Trip to Maui 

Grand prize: Trip for two to Maui. Includes airfare and accommodations.
Enter by: November 15, 2019.
Open to: Age 16 and over.

Miracle Ear Hawaii Cruise Giveaway 

Grand prize: Nine day trip for two to Hawaii. Includes airfare to Honolulu, 7-night NCL Hawaiian Islands cruise.
Enter by: October 31, 2019.
Open to: Legal residents of the US age 55 and over.

PCH Hawaii $50,000 Sweepstakes 

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.

Perfect Days Hawaii Sweepstakes

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 17, 2019.