Escape to the Florida Keys: Win a 4-Night Vacation, Including Air

Need an escape from your everyday life? We’ve partnered with the Florida Keys & Key West to give away the ultimate Florida Keys vacation. The lucky winner and a guest will be whisked away to an island paradise, with luxury hotel stays, airfare, and activities included.

This dream vacation will take you through the highlights of the Florida Keys, beginning at the luxurious Playa Largo Resort & Spa in Key Largo, the northernmost island in this string of around 1,700 coral cays off Florida’s southern coast. You’ll spend two nights at this luxurious resort, which is set on 14 acres of secluded beachfront and features a stunning waterfront pool. 

When you check out of Playa Lago, your idyllic island experience is just getting started. Enjoy one of the world’s most beautiful drives as you make your way down to Key West, where your trip continues at the boutique Lighthouse Hotel, mere steps from iconic attractions like the Key West Lighthouse and Hemingway Home. As Florida’s southernmost point, Key West marks the final stop on this one-of-a-kind Keys adventure.

This epic prize package includes the following:

• $1,250 credit for airfare and ground transportation
• Two nights at Playa Largo Resort & Spa
• Two nights at the Lighthouse Hotel
• Sandbar swim tour package for up to four people with Islander Girl Tours
• Kiteboarding experience for two at the Lagoon at Grassy Key 
• Dinner for two at The Docks Restaurant & Raw Bar
• Two-hour kayak/paddleboard tour for two with Lazy Dog Adventures

How to Enter

Visit our sweepstakes page here to enter before the giveaway ends on May 20, 2024.

Entering is easy—all you have to do is sign up for SmarterTravel and Oyster’s newsletters. If you’re already a subscriber, simply enter your email address to verify your account (you won’t be signed up twice.)

You can gain bonus entries by completing one or more of the following tasks via the Gleam entry page to increase your chance of winning. You’ll receive one additional entry per task.

1. Follow us on Twitter (X).
2. Retweet a Tweet from SmarterTravel.
3. View our Facebook post.
4. View SmarterTravel’s Instagram post.
5. Share the sweepstakes with a friend.
6. Follow us on TikTok.
7. Follow The Florida Keys on Twitter (X).
8. Visit The Florida Keys on Facebook
9. View the Florida Keys’ profile on Instagram

To see the full terms and conditions for the giveaway, visit the sweepstakes page here.