Vacation Sweepstakes and Giveaways 2026
Win a Free Vacation for Your Family
Found 60 total
Wildwood 365 Fall Vacation Giveaway – prize is a 4‑night stay in a Family Suite featuring 3 bedrooms, 2 bathrooms, 2 private balconies, and 4 TVs. Entry ends on September 6, 2026.
Win $600 in value – Wildwood 365 Fall Vacation Giveaway - Enter Now
IOP Escapes Vacation Rentals 3-night Stay Giveaway A 3-night stay at The Beach Blessing. We'll announce the winner on September 18.
Win $900 in value – IOP Escapes Vacation Rentals 3-night Stay Giveaway - Enter Now
Enter the Visit Orlando Common Ground Orlando Sweepstakes for a chance to win an eight‑night Dream Vacation to Orlando, Florida valued at $15,000. The sweepstakes, presented by TripAdvisor, is open to legal residents of the United States, District of Columbia, Canada, Mexico and the United Kingdom who are 21 years or older. The draw will be held on January 7, 2027, so be sure to submit your entry before then. One winner will receive $8,000 in theme‑park funds plus round‑trip airfare, hotel accommodations and a travel planning session. No purchase necessary. This sweepstakes ends on January 7, 2027.
Win $15,000 in value – Visit Orlando Common Ground Orlando Sweepstakes - Enter Now
Toronto Culture Travel Credit Giveaway – one eligible winner will be randomly selected after the giveaway closes on September 12, 2026, at 11:59 PM. @toronto.culture and @shoptravelinc are teaming up to award a $500 shoptravel Travel Credit toward the winner’s next adventure. shoptravel is a Canadian platform helping travellers compare and book hotels and vacation packages with transparent pricing and support. - $500 shoptravel Travel Credit.
Win $500 in value – Toronto Culture $500 CAD Shop Travel Giveaway - Enter Now
Enter Zynga's The First-Class Getaway VIP Sweepstakes.
Prize - $10,000 USD cash plus one Belmond.com gift voucher worth £25,000 GBP (approximately $35,000 USD) for travel and vacation expenses.
Ending Date: September 30, 2026, at 11:59 PM PDT.
Sweepstakes Tip: You can also enter by logging into the Zynga games each day. See rules.
Win $45,000 in value – Zynga's The First-Class Getaway VIP Sweepstakes - Enter Now
Reyes Coca-Cola Bottling Fall Time Sweepstakes offers a Disneyland Resort vacation for the winner plus up to three guests, including up to two consecutive nights at a Disneyland Resort hotel, up to four 2‑day Park Hopper tickets, and one VIP Tour for up to seven consecutive hours. - Disneyland Resort vacation for winner + up to 3 guests, including up to 2 consecutive nights at a Disneyland Resort hotel, up to four 2‑day Park Hopper tickets, and one VIP Tour for up to 7 consecutive hours. Winners: 1. Estimated ARV: $8,040. Ending Date: 9/29/2026 at 11:59 PM PT.
Win $8,040 in value – Reyes Coca-Cola Bottling Fall Time Sweepstakes - Enter Now
Carlie Sack Ultimate Beauty & Wellness Pr Haul Giveaway. One massive Beauty & Wellness PR basket includes:
- Charlotte Tilbury Magic Body Cream
- Charlotte Tilbury Mascara
- Charlotte Tilbury Pillow Talk Blush Stick
- Two Tower 28 Tinted Lip Treatments
- Dae Styling Cream
- Saltair Body Mist
- Bali Body Gradual Tanning Butter
- Coco & Eve Tanning Body Oil
- Orebella Perfume
- Bubble Hydrating Mist & Hydrating Serum
- Snif Body Mist
- Tocca Pistachio Milk Latte Lip Treatment
- Ellis Brooklyn Vanilla Milk / Musk Perfume
- Lune + Aster Bronzing Stick
- Supergoop! (Re)setting 100% Mineral Powder
- Winky Lux Blush, Bronzer & Highlighter sticks
- Medicube Eye Patches
- Vacation "Grand Cuvée" Eau de Toilette
- Yensa Lip Oil
- Monday Haircare Shampoo & Conditioner minis
- Pixi Hydrating Milky Mist
- Pixi Liquid Glow
- Four Curie Pocket Deodorants
- Lemme Debloat Daily Digestive Gummies
- Orebella Assorted Fragrance Discovery Set
- Dr. Sam's Radiance Kit
- Bloom Supergreens Gummies
- Clevr Blends Instant Coffee SuperLatte
Ends on September 12, 2026.
Win $750 in value – Carlie Sack Ultimate Beauty & Wellness Pr Haul Giveaway - Enter Now
Ecommerce Advisors presents the Ecommerce Advisors Big Sur, California Summer Vacay sweepstakes – your chance to win an unforgettable coastal getaway. Enter to win a luxurious escape that combines comfort and adventure in one of California’s most iconic locations.
- 2‑night stay at Treebones Resort plus a $250 resort credit (estimated prize value $1,500)
Vacation sweepstakes entries close on September 10, 2026.
Sponsored by Ecommerce Advisors.
Win $1,500 in value – Big Sur California Summer Vacay Sweepstakes - Enter Now
Stellar Partnership Marketing presents the Luxury Rainforest & Beach Escape to Puerto Rico Sweepstakes – a sweepstakes you’ll want to enter to win a premium island retreat. This free entry giveaway includes an unforgettable prize package valued at over $2,000 for two lucky winners.
- 3‑night/4‑day stay at Wyndham Grand Rio Mar Rainforest, Golf & Beach Resort for two
- Daily breakfast for two
- $200 dining credit for Amaya
- $200 dining credit for Palio
- The Vault Speakeasy Cabaret admission for two
- Pool Cabana at Aura Adult Swim Lounge
- $350 itLuggage Digital Gift Card
- $300 KBH Jewels Gift Card
The vacation sweepstakes closes on September 30, 2026. Enter now for your chance to experience luxury rainforest and beach living in Puerto Rico.
Stellar Partnership Marketing.
Win $3,400 in value – Luxury Rainforest & Beach Escape to Puerto Rico Sweepstakes - Enter Now
The Vintage Compact Shop Vacation Themed Stratton Compact Mirror Giveaway is a sweepstakes you won’t want to miss. Enter to win the stylish Vacation Themed Stratton Compact Mirror, the perfect travel‑ready accessory for any adventure. This giveaway runs now and closes on September 27, 2026.
