Fall in Islamorada

Fewer Crowds, Better Rates & the Same Beautiful Bay

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If you ask a local when the best time to visit Islamorada is, don’t be surprised if they say “fall.” While summer gets the spotlight and winter brings the crowds, fall is quietly one of the best seasons to experience the Florida Keys. And at Kon Tiki Resort, you’ll find lower rates, mild weather, and all the space you need to stretch out and relax.

Here’s what makes fall in Islamorada worth planning for:

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Slower Season = Better Deals

Fall is considered “shoulder season” or "slow season" in the Keys. That means fewer tourists, more open tables at your favorite waterfront restaurants, and better nightly rates on lodging. If you’ve had your eye on a last-minute escape or want to avoid the premium prices of high season, now’s your chance.

We even have select availability at our bayside cottages with dockage—ideal if you're bringing your boat or just want front-row seats to the sunset.

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Mild Weather, Minus the Crowds

By late September and into October, the humidity starts to ease up, and the weather settles into a warm-but-breezy rhythm. Technically we’re still in hurricane season, but it’s winding down. And while we always keep an eye on the forecast, most fall days are perfect for being on—or in—the water.

Plus, fewer people means more room to enjoy your favorite places without the lines or the traffic. Want to visit some of the best beaches near Islamorada? Fall is the time to do it without the usual weekend-warrior crowds.

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More Space, Same Views

There’s something special about Islamorada when it’s quiet. The sunsets still light up the sky. The fish are still biting. And you’ve got a little more room at the bar, on the boat, or by the beach. Whether you’re kayaking through mangroves, biking through town, or just watching the tide roll in, you’ll feel like you have a piece of the Keys all to yourself.

And if you're the type who likes to end the day with a cocktail and a view, check out our Islamorada Happy Hour Guide for the best spots to wind down.

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Local Favorite: Stone Crab Season Begins

Fall also kicks off one of the most delicious times of year in the Florida Keys—stone crab season. Starting October 15, local restaurants begin serving fresh Florida stone crab claws, often caught just offshore the same morning.

From the raw bar at Square Grouper to the chilled platters at Islamorada Fish Company, this is a favorite seasonal treat for both locals and visitors. Pro tip: pair it with a crisp glass of white wine or a cold beer during happy hour, and thank us later.

If you’ve never had fresh stone crab dipped in mustard sauce with a bayside view, fall is the time to change that.

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Make Kon Tiki Your Fall Home Base

Staying at Kon Tiki means you’re right in the heart of it all but with none of the noise. We’re one of the few local resorts with complimentary boat dockage, trailer parking, and a private ramp. No resort fees. No high-season chaos. Just laid-back, Old Florida hospitality with everything you need to make the most of fall in the Keys.

Find out why Islamorada makes the perfect home base for your Florida Keys adventures, and come see why fall might be our best-kept secret.