October 15 Contests: Win A Free Trip to Hawaii Sweepstakes

New contests as of October 15, 2018. Enter Hawaii sweepstakes for a chance to win a free trip to Hawaii. There are ten contests now in progress, including several that end soon. So enter today, before you forget.

You may join the dozens of other lucky people who will be on their way to Hawaii for free. Who doesn’t love a free trip to Hawaii? Cheap flights to Hawaii can’t even touch winning a free trip to Hawaii.

Hawaii sweepstakes spotlight.

In this round of Hawaii sweepstakes, we’re featuring trips to three islands, Kauai, Maui and Oahu, as well as a cash payout contest with a total of $50,000 towards a dream Hawaii vacation of your choice.

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 Contests: Win A Free Trip to Hawaii Sweepstakes

Diamond Resorts Hawaii Sweepstakes

Grand prize: Eleven seven day trips for two to Hawaii (island of your choice), or other destination. Prize includes up to $1,000 airfare, accommodations and $300 cash.
Enter by: September 2, 2019.
Open to: Legal residents of the US except those residing in ID, NE, NJ, PR, WV, and US territories.

Waiakea Volcanic Hawaiian Water Win a Trip to Oahu

Grand prize: Four day trip for two to Oahu. Prize includes airfare, accommodations, helicopter tour.
Enter by: November 5, 2018.
Open to: Residents of North America, South America, Europe, Australia and New Zealand except where prohibited, age 18 and over.

Wellness Creations Hawaiian Adventure Sweepstakes

Grand prize: Four day trip for two to Oahu. Prize includes airfare, accommodations, helicopter tour,
Enter by: October 24, 2018.
Open to: Residents of the US (except Alaska, Hawaii, Rhode Island, Puerto Rico, DC, and other U.S. Territories), age of majority and over.

King’s Hawaiian The Legend of “Hallowaiian” Sweepstakes

Grand prize: Five day trip for four to Oahu. Prize includes airfare, accommodations, plus $1,000.
Enter by: November 30, 2018.
Open to: Residents of the US age 13 and over.

Wanderlust Flow with Intention Sweepstakes

Grand prize: Two 4-day passes to the 2019 Wanderlust Oahu Festival in Oahu plus $1,500 travel stipend.
Enter by: December 1, 2018.
Open to: Legal residents of the United States or Canada, excluding residents of Delaware or Quebec.

Kapalua Maui Sweepstakes/Hawaii.com

Grand prize: Six day trip for two to Maui. Prize includes airfare and accommodations.
Enter by: October 31, 2018.
Open to: Residents of the US age 21 and over.

NYBG Kauai Sweepstakes

Grand prize: Five day trip for two to Kauai. Includes airfare (120,000 Hawaiian Miles (valid for up to 2+ round trips to Hawaii on Hawaiian Airlines, depending on award selected) and accommodations.
Enter by: October 31, 2018.
Open to: Residents of the US age 18 and over.

PCH Hawaii $50,000 Sweepstakes

Grand prize: $50,000. This is a Hawaii themed contest paying cash.
Enter by: October 23, 2018.
Open to: Residents of the US 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, 2019.
Open to: Residents of the US and Canada (except Quebec) age 21 and over.

Updated October 15, 2018.