Vacation Sweepstakes and Giveaways 2026
Vacation Giveaways
Found 48 total
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
Enter the PHX Hydration Energy PHX Pineapple Contest, sponsored by One 11 Brands, for a chance to win a tropical getaway to Waikiki, Hawaii. This sweepstakes is open to legal residents of the United States and the District of Columbia, aged 18 or older. To enter, visit PHX Hydration Energy Drink's Instagram page, find the official Pineapple Contest Post, and respond with a minimum 200-word essay or 30-second video explaining why you deserve a tropical vacation. Alternatively, publish a post on your own public Instagram account, tagging @drink_phx and using the hashtag #PHXPineappleContest. The contest runs from April 27, 2026, to May 16, 2026. One winner will be selected by a panel of judges and will receive a trip for two to Waikiki, Hawaii, including round-trip airfare, hotel accommodations, and a $200 Visa Gift Card, with a total approximate retail value of $4,000. Enter now for your chance to win. One 11 Brands is not responsible for lost, late, or ineligible entries.
Win $3,999 in value – PHX Hydration Energy PHX Pineapple Contest - Enter Now
Enter the Club Med 7-night Stay Giveaway for a chance to win an unforgettable all-inclusive vacation. Win a 7-night stay for 2 adults and 2 children at either Club Med Cancun, Mexico, or Club Med Punta Cana, Dominican Republic. The prize includes a standard room with double occupancy, meals, snacks, and drinks, plus exciting activities. Enter to win this amazing giveaway by May 15, 2026, at 11:59 pm. Don't miss your free entry to win this incredible prize, courtesy of Club Med.
Win $1,000 in value – Club Med 7-Night Stay Giveaway - Enter Now
Enter the Sandals and Beaches Giveaway Q2, 2026 Sweepstakes for a chance to win an all-inclusive 4-day/3-night vacation package for two to a Sandals Resort or Beaches Resort of your choice. To enter, visit www.sandals.com/sweepstakes or www.beaches.com/sweepstakes, or click on online advertisements and provide the requested contact information. You can also refer friends to earn additional entries. The sweepstakes is open to legal residents of the USA and Canada, 18 years or older. The grand prize includes a deluxe suite, all-inclusive amenities, and local airport transfers, with an approximate retail value of $3,054 - $3,538USD. Unique Travel Corp, the worldwide representative of Sandals and Beaches Resorts, is the sponsor of this sweepstakes, administered by American Sweepstakes & Promotion Co, Inc. Enter by June 30, 2026, for your chance to win.
Win $3,054 in value – Sandals and Beaches Giveaway Q2 2026 Sweepstakes - Enter Now
