Updated as of July 15, 2019. Enter Hawaii sweepstakes for a chance to win a free trip to Hawaii. Two contests include Disney Aulani and there is a total of $70,000 in cash. In total, there are fourteen contests available, five of which are brand new. Enter now to be one of the lucky 70 people who will be vacationing in Hawaii for free, before it’s too late. 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.
July 15, 2019 Win A Free Trip to Hawaii Sweepstakes
Hertz Hawaiian Sweepstakes (New)
Grand prize: Seven day trip for four to Maui. Includes first class airfare, accommodations, $20,000 cash, and more.
Enter by: August 31, 2019.
Open to: Legal residents of the contiguous US age 21 and over.
DeltaSkyMag Dream It, Win It! Hawaii Now Sweepstakes (New)
Grand prize: Six day trip for two to Maui and a four day trip for two to Oahu. Includes airfare, accommodations and more.
Enter by: July 31, 2019.
Open to: Legal residents of the US age 21 and over.
Wheel of Fortune Disney Aulani Hawaii Vacation Giveaway (New)
Grand prize: 5 six day trips for four to Oahu. Includes airfare, Aulani accommodations and more.
Enter by: July 20, 2019. Trips are awarded daily.
Open to: Legal residents of the US age 18 and over.
Dole #NoWorries Tradition Disney Aulani Hawaii Vacation Giveaway (New)
Grand prize: Six day trip for four to Oahu. Includes airfare, Aulani accommodations and more.
Enter by: August 4, 2019. Entry is on Facebook with rules found here.
Open to: Legal residents of the US age 18 and over.
Botox #SummerFeels Like A Getaway to Hawaii (New)
Grand prize: Six day trip for two to Oahu. Includes airfare, Aulani accommodations and more.
Enter by: August 39 2019.
Open to: Legal residents of the US age 21 and over.
Polaris Road to Hana Sweepstakes
Grand prize: Three day trip for two to Maui. Includes airfare, accommodations and more.
Enter by: September 22, 2019.
Open to: Legal residents of the US or Canada except Quebec) age 18 and over.
Win a Trip to Kauai (Hawaii.com)
Grand prize: Four day trip for two to Kauai. Includes airfare, accommodations and more.
Enter by: August 12, 2019.
Open to: Those age 21 and over.
Extend Your Summer Sweepstakes
Grand prize: Eight day trip for two to Oahu. Includes airfare and accommodations.
Enter by: August 19, 2019.
Open to: Legal residents of the contiguous US age 18 and over.
Note: Link is to official rules, which contains enter by text instructions.
Monster Hydro Hawaii Sweepstakes
Grand prize: Five day trip for two to Oahu. Includes airfare and accommodations.
Enter by: August 15, 2019.
Open to: Legal residents of the US age 21 and over.
Kona Brewing OneLifeRight Sweepstakes
Grand prize: One winner will receive a trip to Hawaii. (Details not provided).
Enter by: September 4, 2019.
Open to: Legal residents of the US age 21 and over.
Blue Lizard Hawaii Sweepstakes
Grand prize: Seven day trip for four (two adults and up to two children) to Oahu. Includes airfare and accommodations.
Enter by: September 30, 2019.
Open to: Legal residents of the US age 18 and over.
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 (Just extended)
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 July 15, 2019.
Lauren S says
Thank you for compiling this list of giveaways! I’m going to start dreaming of Hawaii now.
Tammy J. says
Hawaii is my happy place!!! Went in 1986 to visit my boyfriend who was stationed there and got engaged at the Hale Koa. Then returned 6 months later to spend the first 2 years of our married life together. Just retuned in 2018 with our two grown daughters and her boyfriend proposed to her on Sunset Beach. So many special memories there. Would love to go back!!! Feel so blessed to have lived and vacationed there!!
TH says
Would love to be picked for any Hawaii trip. My nephew lives there and is getting married May 2020. I’m among the few that cant afford it seeing as though my husband passed away from a heart attack this past Easter. We have a 2yr old little girl and I would love to get away, surprise my nephew and show my little girl that anything is possible.
madeleine m says
I am really sorry to hear about your husband. I hope you are doing well and have all the support you need! Life is preparing something wonderful for you!! Good luck in the contests!! 🙂
Kristin says
My family of eight could really use a vacation. Or even just my husband’s and I. Please.
Karen H. says
If my Mom recovers from cancer…we are going to Hawaii even if I have to take out a personal loan! To win would be heaven sent!
Renate says
Please advice if there is any chance to participate for residents of Europe? Seems there’s no opportunity at all. 🙁 Hawaii has been a dream of mine for like forever. Now it’s me, my husband and 3 kids that dream of a trip like this! Aloha! 🙂
Beat of Hawaii says
Hi Renate.
There are very rarely contests that don’t have a geographical limitation. Not sure why, but that’s just how it is.
Aloha.
Crystal C. says
I really want to go to Hawaii because it been my dream sence i was a kid and till this day it is i love the beaches and wildlife i would love to live up to my dreams one day
Colleen says
I do hope you get to go one day.It is a beautiful and magical place. It was our dream too and it came true! It took us a long, long time, but it happened. Create a plan – start a Hawaii savings fund – even small amounts add up if you give it enough time. Put money somewhere that is not easily accessible. An account with NO debit card attached :0)
Chelsea S. says
🌺 🌺 One day I will take my two daughters 🌺 🌺
Tisha S. says
Please pick us!!! We have never been on vacation. It’s me my husband and our three kids. These kids deserve a vacation without having parents on edge or worrying. They deserve everything good in this world. I’d be forever grateful.
Rohit says
Thank you so much for these amazing getaways! You do a great job! Me and my girlfriend have been living long distance for a while now so we look forward to a dream trip to Hawaii. Cheers!
Beat of Hawaii says
Thanks Rohit.
Good luck.
Aloha.
Jaclyn F says
I would love to go to Hawaii with my Husband. With a little baby and an even bigger stress load at work, he deserves a break. Sometimes all you need is peace and quiet, time with your loving family and a perfect environment to escape and reset!
Colleen says
AMEN! If only everyone could get their dream trip to Hawaii.
Do hope you can go one day. Our best day in Hawaii is just sitting on the beach. Doesn’t cost a thing :0)
Carly R says
The end of this month, my best friend and I are going to HAWAIIIII~ for a week trip and we have been planning this since 2 years ago now. Been on and off about it because its totally out of our(my) comfort zone. Seeing your Hawaii videos, especially this one, made me feel a lot better about going and my excitement is through the roof now.
Looking forward to making memories now. Thanks!
Jennifer G says
Would love to take my son to Hawaii. We’ve never been on vacation really. Could never afford it and he’s now 17. This would be a chance of a lifetime and working 2 jobs just to pay rent and bills no money left for luxuries like a vacation.
Kimberly says
Thanks for having such a great contest!!!! Please congratulate the winner!!!!
Erin O says
Thank you so much for posting these! Is there any way to call out the new additions since last posting? I keep forgetting which ones I’ve already entered and I don’t want to mess up my chances entering again.
Beat of Hawaii says
Hi Erin.
Thank you. That’s a good idea and we will implement it soon.
Aloha.
Bretaina says
I really want to go to Hawaii because me and my family don’t have money like that and I’m really hoping I win and hope you see this
Jeanne H. says
Thank you for the great information you continually offer! I have posted here a few times and can’t seem to find where your response to me can be found. I need to book eight people from Sacramento to Maui June 29 and returning July 6th. My question is should I wait for Southwest or book now while flights are available? Roundtrip seems to be hovering at about $1,100. per person (gasp!). Would greatly appreciate your advice. Thank you in advance, Jeanne
Beat of Hawaii says
Hi Jeanne.
We did receive this comment and the one from yesterday, but there were none before that.
Assuming that Southwest does announce, it is highly unlikely that fares at end of June will be discounted. Discounts will probably be from mid-August on.
You’re dates are among the most expensive of the year. We find nonstop on Alaska at $817 for your dates. Not horrible, and do keep in mind that non-stop flights could easily become sold out on those Saturdays.
Aloha.
Bonnie says
Please.