March Madness is back — and so is our Annual NCAA Bracket Challenge hosted by Dan’s Florida Condos.

The best part?

You don’t need to be a basketball expert to win. In fact, some of our past winners didn’t know the difference between a layup and a three-pointer! Whether you follow college basketball all season or just enjoy the madness of the tournament, this challenge is for you. Make your picks here, follow the games, and you could be packing your bags for Anna Maria Island.

🏆 Grand Prize

The winner of the Anna Maria Island NCAA Bracket Challenge will receive:

🌴 One FREE week at one of Dan’s Florida Condos vacation homes

Valid for stays between April 19, 2026 – December 20, 2026

Enjoy seven miles of beautiful beaches, award-winning waterfront restaurants, and sunsets over the Gulf of Mexico.

🚨 How to Enter (3 Quick Steps)

Step 1 – Fill Out Your Bracket

Click here to set up an account and submit your bracket through CBS Sports.

Join the pool titled: Anna Maria Island NCAA Bracket Challenge

⏰ Brackets must be submitted before the first game tips off Thursday, March 19 at 12:15 PM EST.

Step 2 – Follow Dan’s Florida Condos on Social Media

Participation requires engagement on our social channels. This is where standings will be broadcast, along with special offers throughout the tournament. You won't want to miss out!

Follow us here:

Facebook: https://www.facebook.com/dansfloridacondos

Instagram: https://www.instagram.com/dansfloridacondos

Step 3 – Like, Comment, and Share the Contest Post

To qualify for the prize:

✔ Like the contest announcement post (Like now...)

✔ Comment on the post (Comment now...)

✔ Share it with friends (Share Now...)

This helps spread the March Madness fun and confirms your entry.

🎯 No Strategy Required

Not sure how to pick a bracket? Perfect.

Many people choose based on:

• Favorite mascots

• School colors

• Random guesses

• Copying a friend’s picks

That’s part of the fun. Anything can happen in March Madness.

🌴 About Dan’s Florida Condos

Dan’s Florida Condos offers beautiful vacation homes right on Anna Maria Island, known for its white-sand beaches, turquoise waters, and laid-back island charm — just 50 minutes south of Tampa and 20 minutes from Sarasota.

Many of our condos are located in the popular Runaway Bay community, just across the street from private beach access and home to some of the island’s best amenities, including the largest heated saltwater pool on Anna Maria Island, a bayfront fishing pier, and easy walkability to restaurants and shops.

Our fully stocked one- and two-bedroom condos make it easy to settle in and enjoy everything the island has to offer.

🌊 The beaches are beautiful, the island is thriving, and your next getaway is waiting.

⚖ Contest Fine Print

• Prize includes one Saturday-to-Saturday stay (April 6, 2026 – December 19, 2026), subject to availability and blackout dates; unit assigned by Dan’s Florida Condos • Prize is non-transferable, has no cash value, and must be booked within 6 months of winning • Winner is responsible for taxes, fees, and any incidental charges; signed rental agreement, valid ID, and damage waiver or deposit may be required • Airfare and transportation are not included • Must be 18+ to enter; fraudulent or duplicate entries may be disqualified • Ties will be resolved by Dan’s Florida Condos; all decisions are final • Social media participation required; CBS Sports, Facebook, and Instagram are not sponsors or administrators • Dan’s Florida Condos reserves the right to modify or cancel this promotion • Promotion may not be copied or redistributed without written permission

🏀 Ready to Join the Madness?

Submit your bracket and you could be enjoying a free week on Anna Maria Island.

👉 Click here to enter the CBS Bracket Challenge

Good luck — and may your bracket survive the madness.