New contests added March 18, 2019. Enter Hawaii sweepstakes for a chance to win a free trip to Hawaii. There are eleven contests available now and one that ends tonight. Enter today, before it’s too late. 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 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
Hawaiian Airlines New Mobile App Sweepstakes
Grand prize: 140,000 HawaiianMiles from Hawaiian Airlines. Depending on award selected, valid for up to 3 round trip tickets between North America and Hawaii.
Enter by: March 18, 2019.
Open to: Legal residents of the US states age 18 and over.
Wellness Wanderlust Sweepstakes
Grand prize: $400 airfare voucher and $3,000 Pravaasa gift certificate for a trip for two to Maui.
Enter by: March 30, 2019.
Open to: Legal residents of the US states (except, Alaska, Hawaii and Rhode Island) age 18 and over.
Ultimate Spring Break Sweepstakes
Grand prize: $10,000.
Enter by: April 1, 2019.
Open to: Legal residents of the US states age 21 and over.
Dollar Flight Club Hawaii Sweepstakes
Grand prize: Two round trip tickets to Hawaii (valued up to $1,000).
Enter by: March 31, 2019.
Open to: (Not stated).
Win a Surf Trip to Hawaii Sweepstakes
Grand prize: Four day trip for two to Oahu. Includes airfare, accommodations and private surf lessons. Or $4,000 gift card.
Enter by: May 31, 2019. Note that entry is via text message (see official rules).
Open to: Legal residents of the US states age 21 and over.
Temptation Island Tropical Getaway Sweepstakes
Grand prize: Six day trip for two to Hawaii (destination determined by sponsor). Includes airfare and accommodations.
Enter by: March 27,2019
Open to: Legal residents of the 48 contiguous US states age 18 and over.
Hawaii Magazine Win an Oahu Vacation
Grand prize: Five day trip for two to Oahu. Prize includes airfare and accommodations.
Enter by: April 30, 2019.
Open to: No limitations indicated.
Note: There is a $10 fee to enter this contest, together with a submitted travel video (up to 60 seconds).
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.
PCH Hawaii $50,000 Sweepstakes
Grand prize: $50,000. This is a Hawaii themed contest paying cash.
Enter by: June 25, 2019.
Open to: Legal rResidents 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, 2020
Open to: Residents of the US and Canada (except Quebec) age 21 and over.
Win a Trip to Hawaii from the Arizona Renaissance Festival
Grand prize: Trip for two t Hawaii. Includes first class airfare and $2,000 cash.
Enter by: March 31,2019
Open to: Residents of Arizona age 18 and over.
Updated March 18, 2019.
Photo at Hanauma Bay, Oahu.
Nicole S says
My husband had always wanted to take me to Hawaii for our 10 year anniversary and that so happens to be this year 🙂
Tammy says
Well, I’m an old school Hawaii lover. I’ve been going every year since I turned 17. Winning a trip, well, that’s WINNING.
MAHALO for posting these up for us. I don’t mind giving out my info, I got email unsubscribe and call blockers in place. Good luck ohana, seas yous at the swim up tiki bar. ALOHA!
Ronald S says
We are 72, grew up together then did see each other after High School for 40 years. Got married 2010 and try to go to Hawaii every chance we can. Our love of Hawaii has allowed us to personally influence over 20 couples to go to Hawaii for vacation. Mahalo!!!
Shawn F says
Thank you! I am like many of your fans who are trying to win a trip to Hawaii. I went as a child once and it felt like home. Tears streamed my face as I heard the Polynesian drumming and dancing. My husband knows that I have wanted to take my kids for a very long time. My older two kids had to grow up quickly because I am a double above knee amputee, as well as few other issues, like insomnia. My daughter has the same genetic condition. A combined number of surgeries that my family hS experienced is 53 surgeries. We never could save for an trip other than a long weekend at someplace close to home. I’m losing more function neurologically and I truly fear that if I can’t find a way to go on the next year, then I might never actually get there. I want to be able to walk some. So please, this is the perfect time …. please choose us!
Jan G says
Would love to join our family in Hawaii for a vacation!
Philip R says
Been w my gr8 14 yrs..not MARRIED yet. We r 42. 43..never had 1 vacation un our life..my ol lady want to go here bad.. I no we would come back married..we no family but loot it takes to go sumwgere great
Carl M says
Sorry. Love your site but not giving all this personal info to a third party for a sweepstakes
Keep up the beat!!
Charlene says
How exciting I would love to win a magnificent prize to see one of many beautiful places on earth❤️
Kathleen T says
We have never had the money to take our 3 kids on a vacation or go on our own. Our twins have some disabilities and this would be amazin to either take kids or take a quiet trip for two.
Catalina B. says
My husband of 50 years of marriage and I, would love to celebrate our 51st Wedding Anniversary in Hawaii. Last year, as well as all other years, we could not afford the trip. Please consider the importance of this trip to a senior couple that has not been able to make the trip on our own. It would be a Godsend. Thank you, C&L
Charles L says
I would like to go to Hawaii to see my grand daughter for the summer.
Rose M says
AFTER 25 YEARS OF MARRIAGE, THIS WOULD BE A GREAT TRIP TO SPEND QUALITY TIME WITH OUR COLLEGE AGE ‘ADULTS’
Linda S says
This would be so exciting. Thank you
Patti S says
Perfect place. Our son proposed on Waikiki.. would be great to have his wedding there too.
Amy says
I would love to take my three children on a vacation of their dreams!!