Vacation Sweepstakes and Giveaways 2026
Vacation Giveaways
Found 66 total
Enter the MSC Cruises 7-Night Caribbean Cruise Sail Into Paradise Cruise Giveaway Sweepstakes, sponsored by OLA Vacations, Inc., for a chance to win a fantastic cruise prize. This exciting giveaway offers a balcony cabin for two on an MSC Cruises 7-Night Caribbean cruise, with an approximate retail value of $3,200. To enter, simply visit the sweepstakes site and complete the entry form, or use the free alternate method of entry by mailing in a 3x5 card with your contact information. The promotion period runs from May 13, 2026, to June 12, 2026, and is open to legal residents of the United States and the District of Columbia who are at least 21 years old. One entry per person is allowed, and the winner will be selected in a random drawing on or about June 22, 2026. Don't miss this opportunity to sail into paradise with OLA Vacations, Inc. and MSC Cruises.
Enter the Ultimate Florida Vacation Sweepstakes, courtesy of VISIT FLORIDA, for a chance to win an unforgettable 6-day, 5-night trip to Stuart, Florida. This incredible prize package, valued at $6,610, includes round-trip airfare, accommodations at the Marriott Hutchinson Island Beach Resort, Golf & Marina, and exciting activities like an eco-tour adventure and a sunset cruise. To enter, simply visit the Website and provide your contact information between May 20, 2026, and June 14, 2026. You can enter once per day, with a limit of 26 entries per person. The grand prize winner will be selected in a random drawing on June 16, 2026. Don't miss this opportunity to win a dream vacation - enter the Ultimate Florida Vacation Sweepstakes today, courtesy of VISIT FLORIDA.
Win $6,610 in value – Ultimate Florida Vacation Sweepstakes - Enter Now
Ready for a hair care transformation? Enter the Sally Beauty Hair Care Giveaway for a chance to win a collection of top-notch hair care products, including Eva NYC's H2-Whoa Hydrating Shampoo and Conditioner, Stay Hydrated Leave-In Conditioner, and Balance It All Hydrating Scalp Serum, as well as ion 24k's Charcoal Detox Shampoo, Metal & Mineral Neutralizing Spray, and ion's Sun Care Heat Protective Spray. Get a free entry to win these amazing hair care prizes from sallybeauty and achieve the ultimate post-vacation hair glow-up.
Win $139 in value – Sally Beauty Hair Care Giveaway - Enter Now
Get ready to kick off summer with the Advocare Summer Giveaway. Enter to win the ultimate summer starter pack, valued at $395, featuring an Igloo Legacy Cooler, Bink Bottle, Vacation SPF 50, a red and white checkered beach towel, and exclusive AdvoCare products, including a Tiger's Blood Snow Cone pool float, canister, and bag. Don't miss your chance to win this amazing prize and make your summer unforgettable with AdvoCare.
Win $395 in value – Advocare Summer Giveaway - Enter Now
Enter the NEA Member Benefits FY26 Annual Giveaway Sweepstakes for a chance to win a fantastic prize. Between April 6, 2026, and June 29, 2026, NEA members can enter by registering at www.neamb.com or calling 1-800-637-4636, providing their complete name, mailing address, and email address. Limited to one entry per eligible NEA member per day, with a total of two potential winners to be selected in a random drawing. The prize includes a cruise certificate for a four-night cruise to Mexico or the Caribbean, plus $250 in Vacation Cash, with an approximate retail value of $950. Open to NEA members who are 18 years or older and legal residents of the U.S. or the District of Columbia. Enter to win this amazing giveaway, courtesy of NEA Member Benefits.
Win $950 in value – NEA Member Benefits FY26 Annual Giveaway Sweepstakes - Enter Now
Enter the Alaska Air This Is The Way Sweepstakes for a chance to win an epic prize package. Join forces with Alaska Airlines, @Disneyland Resort, and @themandalorian to celebrate #TheMandalorianAndGrogu in theaters now. You could win a vacation package to the Disneyland Resort in Anaheim, California, including round-trip air travel for two on Alaska Airlines, a 2-night stay at a Disneyland Resort Hotel, 4 one-day park hopper tickets, and Fandango gift cards to see Star Wars: The Mandalorian and Grogu. The approximate retail value of the prize is $4400. To enter, follow @alaskaair on Instagram, use the hashtag #AlaskaAirThisIsTheWaySweepstakes, and follow the instructions on the sweepstakes post during the sweepstakes period from May 26, 2026, to June 2, 2026. Open to legal US residents, 18 years or older. No purchase necessary. See official rules for details. Alaska Airlines is the sponsor of this sweepstakes.
Win $4,400 in value – Alaska Air This Is The Way Sweepstakes - Enter Now
Enter the Grand Circle Corporation 2026 Summer Vacation Ambassador Referral Sweepstakes for a chance to win a grand prize of $6,500 in cash or travel credits. Sponsored by Grand Circle LLC, this sweepstakes is open to legal US residents, excluding CO, FL, NY, and RI, who are 18+ years old. No purchase necessary, and odds of winning depend on the total number of eligible entries. To enter, refer a new customer to book a trip with Grand Circle between April 26 and July 15, 2026, or mail a postcard with required information to Grand Circle LLC by July 15, 2026. Ten winners will be selected in a random drawing on July 27-31, 2026. Winners will receive their choice of cash or travel credits, with a total prize value of $6,500 or $3,500. Grand Circle is responsible for shipping the prize, but winners are responsible for taxes and fees. Enter now for a chance to win a dream vacation, courtesy of Grand Circle Corporation 2026 Summer Vacation Ambassador Referral Sweepstakes.
Get ready to win an unforgettable experience with the Ocean City New Jersey Free Family Vacation Contest. Enter to win a fantastic 7-night getaway to Ocean City, New Jersey, courtesy of the Ocean City Tourism Commission. One lucky winner will be selected on or about Monday, July 6, 2026, to enjoy a free vacation in a stunning 3-bedroom, 2-bathroom OCNJ Condo, perfect for a family of up to 8 people. The prize includes 7 nights of accommodations, from Saturday to Saturday, in a great location within walking distance of the beach. Enter now for a chance to create lifelong memories with your loved ones in Ocean City, New Jersey, with the Ocean City Tourism Commission.
Win $4,000 in value – Ocean City New Jersey Free Family Vacation Contest - Enter Now
Enter the cksquared_boutique May Giveaway for a chance to win an incredible 4-night, 5-day all-inclusive getaway to Sandals Barbados resort or a cash alternative of $4,000 plus a $1,000 CK shopping spree. This amazing sweepstakes offers a free entry to win a prize valued at over $5,000. Don't miss out on this opportunity to win big and indulge in a luxurious vacation or a cash prize and shopping spree with cksquared_boutique.
Win $6,000 in value – CKsquared Boutique May Giveaway - Enter Now
Enter the VisitFortMyers You Deserve a Shell-cation Giveaway for a chance to win a fantastic Grand Prize. One lucky winner will receive a three-night stay for up to four people at the Sundial Beach Resort & Spa in Sanibel, FL, complete with a two-bedroom Garden View unit and access to resort recreation like bikes, kayaks, and paddleboards. The prize also includes a $2,000 pre-paid Visa Gift Card for travel and expenses. With an approximate retail value of $4,830, this giveaway is an opportunity you won't want to miss. Enter to win this incredible prize and make your dream vacation a reality with VisitFortMyers.
Win $4,830 in value – VisitFortMyers You Deserve a Shell-cation Giveaway Sweepstakes - Enter Now
