Florida Keys

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Florida Keys

The iconic Overseas Highway off the southern tip of Florida stretching outside of Miami across the Florida Keys connects travelers to a world filled with turquoise waters, tropical savannas, and a relaxed pace of life. The breathtaking drive linking this sun-drenched chain of islands from Key Largo to Key West, crosses 42 bridges before reaching the southernmost point in the continental U.S.

This is the Florida Keys, an island getaway that attracts diverse but highly intentional travelers seeking sun, sandbars, inspiration, and festivities. The Florida Keys welcome over 5 million people yearly, offering an idyllic vacation spot where the Gulf meets the Atlantic.

People are attracted to the Florida Keys for boating, world-class fishing, spectacular snorkeling and diving along North America's only living coral barrier reef. Don’t forget the simple pleasure of watching the sun set over the ocean - frequently to the echo of applause and celebration in Key West.

In the early 20th century, Henry Flagler’s Over-Sea Railroad connected the Keys through a feat of engineering that linked the isolated islands. While the railroad was later damaged, this paved the way for today’s sunkissed island hopper highway weaving its way south. With each mile traveled along this highway there’s a sense of leaving behind the hustle and bustle of everyday life, freeing one up for the ultimate Florida beach vacation.

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Florida Keys

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The Florida Keys offer unique communities across a more than 100 mile string of tropical islands off the southern tip of Florida. Our Casago Florida Keys team understands what makes this destination special and celebrates the distinct charm to be found across the Keys.

This unique island escape has an elevated laid-back, tropical, and vibrant atmosphere, offering a peaceful getaway to the ‘American Caribbean.’ From snorkeling and world-class diving in Key Largo to the lively energy of Key West and the family-friendly boating community in Marathon, the Florida Keys provide a range of experiences for visitors of all ages.

Our Casago Florida Keys team is dedicated to providing our homeowners and guests with the utmost care, while providing for a seamless and memorable island getaway.

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Frequently Asked Questions

When is the best time of the year to visit the Florida Keys?

There really isn’t an off season for the Florida Keys. With that said, many consider peak season to be from mid-December thru April, offering terrific weather, low humidity, and great fishing. This is a particularly popular time for “snowbirds” from the north, with November through February touted as the best months. March thru May start to see fewer crowds as the winter flocks start to head home. Summer on the Florida Keys continues to draw visitors, providing a perfect fit if you prefer a less crowded, warm ocean, and are not shy for humidity and very warm temps.

Do I need a car in the Florida Keys?

Yes, for most areas. Exception: Key West is walkable/bike-friendly. The area is electric car friendly but keep in mind Key West is limited with parking spaces. Check if your property has a parking spot.

What’s the best way to fly to the Florida Keys?

Key West International Airport (EYW) provides several commercial flights directly to the Keys, though Miami International (MIA) is the nearest major airline hub. Renting a car in Miami and driving across the Overseas Highway offers a stunning scenic drive to kick-off your stay.

For travelers flying into Miami International, approximate drive times along the Keys:

Key Largo – 1 hour
Islamorada – 1.5 hours
Marathon – 2 hours
Key West – 3.5–4 hours

What are the biggest events in the Florida Keys?

The Florida Keys is home to many big festivals throughout the year. Some of the most iconic of these take place in Key West and include:

Fantasy Fest (Late October) - This unique weeklong event is a showstopping affair among annual festivals on the Keys, offering extraordinary opportunities to pull out your best costumes for the Zombie Bike Ride and Deep Eddy Vodka Fantasy Fest Parade
Hemingway Days (July) Three day festival celebrating the life of Ernest Hemingway
Just a Few Friends (September) Celebrating Jimmy Buffet’s legacy of island music, food, and fun
Florida Keys Lobsterfest - (August ) Kickoff to lobster season
Key Lime Festival (July) - Well of course there’s a festival to celebrate the Keys’ most popular dessert, while highlighting the area’s unique culture.

Florida Keys

Locally Owned & Operated

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Book with Confidence

Book with Confidence

Verified Guests and Owners

Casago Support & Security

Franchise with Casago

Franchise with Casago

Verified Guests and Owners

Team Training

Our Guarantee

Frequently Asked Questions

When is the best time of the year to visit the Florida Keys?

Do I need a car in the Florida Keys?

What’s the best way to fly to the Florida Keys?

What are the biggest events in the Florida Keys?

More questions?