Vacation Sweepstakes and Giveaways 2026
Vacation Giveaways
Found 65 total
Travel With The Ewings is excited to send one lucky winner on a Disney vacation valued at $3,000. This giveaway is open to U.S. residents ages 18+ and ends on May 22, 2026, at 8pm EST. The winner will be randomly selected and announced on May 23, 2026, at 8pm EST. To enter, follow Travel With The Ewings and tag friends in the comments who would love a Disney vacation. This is a free entry giveaway with one winner. Enter to win a dream Disney vacation and make your dreams come true.
Win $3,000 in value – Travel With The Ewings Disney Vacation Giveaway - Enter Now
Enter to win the Ventura County Coast Ultimate Trip to Ventura County Coast Contest Sweepstakes, a fantastic giveaway courtesy of Ventura County Coast. Anyone over 18 is eligible to win this incredible prize package, valued at a stunning getaway. The prize includes a 3-night stay at one of 60+ hotels in Ventura County Coast, a Channel Islands National Park trip for two, and a Ventura County Coast Swag Bag. To enter, simply sign up for the newsletter or follow on Instagram between April 1st, 2026, and June 30th, 2026. If you've already subscribed within this date range, you're automatically entered to win. The winner will be chosen at random after the contest deadline ends on June 30th, 2026, at 11:59am PST, and notified via email. With 12 months to book your trip, you can plan your dream vacation to Ventura County Coast, courtesy of Ventura County Coast.
Enter the Jamaica Flyaway Instagram Contest, courtesy of iHeartMedia + Entertainment, Inc., for a chance to win an incredible 4-day, 3-night all-inclusive vacation for two to a Sandals Resort in Jamaica, valued at up to $5,062. To participate, follow @hot995 on Instagram, like a contest post, and comment by tagging a friend. The contest starts on May 18, 2026, and ends on May 29, 2026. One winner will be randomly selected and notified via direct message. No purchase necessary, and the contest is open to US residents 18+ who reside in specific counties. iHeartMedia + Entertainment, Inc. brings you this exciting sweepstakes, so enter now for your chance to win a dream getaway to Jamaica.
Win $5,062 in value – Jamaica Flyaway Instagram Contest - Enter Now
Enter the Margaritaville Beach Resort Hollywood Beach Resort Story Contest, a skill-based contest where chance plays no part in determining winners. Margaritaville Hollywood Beach Resort invites you to share your story for a chance to win exciting prizes. The grand prize includes a two-night family vacation stay at Margaritaville Beach Resort Hollywood Beach, a one-day poolside cabana, a 30-minute FlowRider experience, and a $250 dining resort credit. Two runners-up will receive a Margaritaville Swag Bag with a $50 gift card. To enter, submit a photo of your stay at the resort, taken by you, with a digital file that complies with the submission requirements. Limit one entry per person. No purchase necessary to enter or win. Open to individuals who have reached the age of majority in their jurisdiction of residence. Employees of Margaritaville and their immediate family members are not eligible. Contest is void where prohibited. Enter now for your chance to win with Margaritaville.
Win $1,500 in value – Margaritaville Beach Resort Hollywood Beach Resort Story Contest - Enter Now
LOFT is giving away a summer getaway package to one lucky winner, including a LOFT July suitcase and tote in the color of their choice, plus a $200 LOFT gift card for vacation-ready looks. The sweepstakes runs from 5/14-5/21 and is open to U.S. residents, 18+. Enter to win this amazing prize package by following LOFT on Instagram. Void where prohibited by law.
Win $200 in value – LOFT Summer Getaway Giveaway - Enter Now
Lauren Ashley Hansen's 30A Vacation Giveaway: Win a magical 5-night stay in Florida with family and friends, valued over $4,500. The prize includes a beach home with bed, bath, golf cart, bikes, and pool, pastries and coffee from a local coffee shop, and a shopping trip to Cabana Seaside and The Seaside Style. One winner will be randomly selected on June 1st. Enter by following the post, commenting, and tagging friends for extra entries. Reshare and share your story for a bonus entry. This giveaway is not affiliated with Instagram.
Win $4,500 in value – Lauren Ashley Hansen 30A Vacation Giveaway - Enter Now
Get ready to win big with the Ava Resort Cancun Giveaway Sweepstakes, courtesy of Fun Jet Vacations. Enter to win an unforgettable 3-night trip for two adults at the stunning Ava Resort Cancun, complete with a standard hotel room. Imagine sharing this incredible experience with a friend or loved one in beautiful Cancun. Take a moment to enter for a chance to claim this amazing prize, courtesy of funjetvacations.
Win $2,000 in value – Ava Resort Cancun Giveaway Sweepstakes - Enter Now
As Revival's Summer Launch Giveaway is here, celebrating with a sweepstakes where TWO lucky winners will receive a $200 Revival gift card each to refresh their summer wardrobe. Enter to win by following, liking, saving, and sharing this post, and commenting your dream summer vacation below. Bonus entries are available by showing love to As Revival's posts this week. Winners will be announced on May 20, 2026. This giveaway is open to residents 18+ and is not sponsored or endorsed by Instagram. Enter for a free chance to win one of two $200 gift cards and make your summer dreams come true.
Win $400 in value – As Revival Summer Launch Giveaway - Enter Now
Enter the Give Kids The World 2026 Dreams Unlimited Travel Disney Cruise LINE Sweepstakes for a chance to win a 4-Night Disney Cruise Line vacation for 2. To enter, make a donation to Give Kids The World at https://www.gktw.org/DreamCruise or mail a 3" x 5" card with your contact info to PO Box 595, Social Circle, GA 30025-0595. Sweepstakes runs from May 13, 2026 to June 10, 2026. Open to US residents 18+, void where prohibited. Prize valued at $3,000. Give Kids The World, Inc. is the beneficiary of this sweepstakes, with Dreams Unlimited Travel donating the prize package.
Enter the Just Blessed Giveaway for a chance to win a magical trip to Walt Disney World Resort in Orlando, Florida. Just Blessed is excited to offer this incredible prize, valued at a fantastic package including round-trip economy airfare, 2-night hotel accommodations, and a 1-day Disney Park admission ticket. To enter, simply purchase the Just Blessed Bundle on Walmart.com or submit a free mail-in entry to Just Blessed, 1031 Exchange Place Suite 107 St Cloud, Florida 34769, or email [email protected] with your contact information. The giveaway is open to legal US residents, 18 years or older, with a maximum of one entry per person. The promotion ends once 200 qualifying entries are received, and a winner will be selected by random drawing. Just Blessed will cover reasonable travel expenses for out-of-state winners. Don't miss this opportunity to win a dream vacation, courtesy of Just Blessed.
Win $3,000 in value – Just Blessed Giveaway - Enter Now
