Vacation Sweepstakes and Giveaways 2026
Vacation Giveaways
Found 49 total
Enter to win the "Dole Your Way to Hawaii" Contest for a chance to take home an unforgettable prize. The grand prize, valued at $20,000 CAD, includes a 6-day, 5-night vacation for two to Hawaii, featuring round-trip economy airfare and accommodations at a hotel specified by the Sponsor. The prize must be accepted as awarded and is non-transferable. Contest closes on May 19, 2026, at 11:59:59 pm ET, so submit your free entry now for a chance to win this incredible getaway to Hawaii with Dole.
Win $20,000 in value – The Dole Your Way to Hawaii Contest - Enter Now
Enter the Renting The Coast 5 Night Giveaway for a chance to win an unforgettable 5-night stay at "Sea into your Soul" in beautiful Cape San Blas, Florida. This incredible prize is up for grabs, and the winner will be chosen on May 30th, 2026. Don't miss your opportunity to win this amazing getaway - enter to win now and make your dream vacation a reality with Renting The Coast.
Win $2,500 in value – Renting The Coast 5 Night Giveaway - Enter Now
Enter the 717 Supply 2026 Chevrolet Tahoe Z71 #45 Sweepstakes for a chance to win an incredible grand prize. The Grand Prize Winner will be awarded one of two exciting options: Option 1, featuring a 2026 Chevrolet Tahoe Z71 valued at $90,000, a $10,000 check, and a dream vacation for the winner and their guests up to $10,000, or Option 2, a $75,000 check. Don't miss this opportunity to win a life-changing prize - enter to win today with a free entry in the 717 Supply 2026 Chevrolet Tahoe Z71 #45 Sweepstakes.
Win $110,000 in value – 717 Supply 2026 Chevrolet Tahoe Z71 #45 Sweepstakes - Enter Now
Enter to win The Edge’s Alt-imate Escape To Jamaica Contest for a chance to escape to paradise. This incredible sweepstakes giveaway offers a seven-day/six-night All-Inclusive vacation for two at one of the luxurious Sandals Resorts in Jamaica, including Sandals Ochi, Sandals Dunn’s River, Sandals Negril, Sandals Royal Plantation, Sandals Montego Bay, Sandals South Coast, or Sandals Royal Caribbean. The prize package also includes $2,800 USD towards return airfare for two. Don't miss your chance to win this amazing prize, valued at a total of over $2,800. Enter now for your free chance to win before the deadline of May 8, 2026.
Win $9,172 in value – The Edge’s Alt-imate Escape To Jamaica Contest - Enter Now
Enter the Paradise Adventures 7 Night Stay Giveaway for a chance to win an unforgettable 7-night getaway to a destination of your choice, courtesy of Endless Vacation Rentals. This exciting sweepstakes offers a free entry to win a prize that could be your dream vacation. Don't miss out on this opportunity to make your travel dreams a reality and enter to win now.
Win $1,200 in value – Paradise Adventures 7 Night Stay Giveaway - Enter Now
Enter the Vendors of Dodge County Tourism, The "Spring into Dodge County Sweepstakes" for a chance to win one of two exciting Dodge County vacation packages valued at over $500 each. These incredible prize packages are packed with perks like lodging, event tickets, dining gift certificates, and spending money. Prize Package #1 includes a one-night stay at Mayville Inn, tickets to the Taste of Wisconsin Beer, Cheese & Wine Fest, and more. Prize Package #2 features a two-night camping stay at a Dodge County Park, golfing at Horicon Hills Golf Club, and other fantastic experiences. Enter to win by 12:00:00p.m. on June 3, 2026, for your free chance to take home one of these amazing prizes.
Enter The Grandview Condos 5-Night Stay in Paradise on Grand Cayman Giveaway for a chance to win a dream vacation. One lucky winner will receive a 5-night stay in a 2-bedroom condo, accommodating up to 4 guests, on stunning Seven Mile Beach. Don't miss this free entry opportunity to win a paradise getaway - enter to win before the deadline of January 15, 2027.
Win $4,250 in value – Grandview Condos 5-Night Stay in Paradise on Grand Cayman Giveaway - Enter Now
Enter the Ricky Smiley Morning Show Disney Dreams Vacation Giveaway for a chance to win an unforgettable 4-day getaway to Walt Disney World® Resort. One lucky Grand Prize winner will receive a prize package, courtesy of the Rickey Smiley Morning Show, including round-trip airfare for four, ground transportation, a standard room for three nights, and up to four 4-Day Theme Park Tickets with Park Hopper® Option. Valued at a fantastic price, this prize package is up for grabs until 11:59 pm ET on Friday, May 22, 2026. Take a free entry to win with the Ricky Smiley Morning Show Disney Dreams Vacation Giveaway, a sweepstakes promotion from the Rickey Smiley Morning Show.
Win $7,617 in value – Ricky Smiley Morning Show Disney Dreams Vacation Giveaway - Enter Now
Enter the Apple Vacations PowerReviews Giveaway Sweepstakes for a chance to win a grand prize. The sweepstakes, sponsored by Apple Vacations, begins on May 1, 2026, and ends on July 1, 2026. To enter, leave a review about your booking experience on PowerReviews and fill out the information on the giveaway entry landing page. The grand prize includes a standard resort room for two adults for three nights at any participating RIU property, with an approximate retail value of $2,000. Winner will be selected via random drawing and notified via email. Apple Vacations reserves the right to modify or terminate the sweepstakes at any time. By entering, you agree to the official rules and grant Apple Vacations the right to use your name and likeness for promotional purposes. Enter now for a free chance to win this amazing prize, courtesy of Apple Vacations.
Win $2,000 in value – Apple Vacations PowerReviews Giveaway Sweepstakes - Enter Now
Enter the Dad's Guide Coolest Summer Ever Sweepstakes, courtesy of WDW Magazine, for a chance to win an unforgettable Walt Disney World vacation package. This amazing prize, provided by Disney Destinations, LLC, includes round-trip airfare, ground transportation, accommodations, 4-Day Theme Park Tickets with Park Hopper Option, and a $300 Disney Gift Card, with an approximate retail value of $7,917.76. To enter, visit www.wdw-magazine.com/coolestsummerever and complete the online entry form between April 28, 2026, and May 17, 2026. Open to legal residents of the 50 United States and DC, aged 18 or older. Limit one entry per person, with additional entries available through bonus actions. Travel must be completed by May 31, 2027. WDW Magazine brings you this incredible sweepstakes, so enter now for your chance to win a magical Disney getaway.
Win $7,900 in value – Dad's Guide Coolest Summer Ever Sweepstakes - Enter Now
