Trip Planning

Things to Do in Historic Key West: A First‑Time Visitor’s Guide

Planning your first Key West vacation? You’re in for a trip full of sunshine, pastel-colored streets, waterfront views, and plenty of history mixed in with the fun! You never know just what you’ll find here! Old Town Key West is where many first-time visitors spend...Read more
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Trip Planning
overseas highway

Driving to Key West from Fort Myers vs. Miami

Key West is easily drivable from many locations in Florida. Today, we’ll focus on driving to Key West from Fort Myers vs. Miami.Read more
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Trip Planning
book direct with dwell key west

Celebrate Book Direct Day with a Vacation to Key West

Celebrate Book Direct Day on February 4th, 2026, by booking a vacation to Key West, directly with us at Dwell Key West! We can't wait to see you.Read more
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Trip Planning
beach chairs in key west budget-friendly vacation

Your Guide to a Budget-Friendly Key West Vacation

Planning a vacation to Key West, but worried about your budget? You’ve come to the right place. Here’s the ultimate guide to a budget-friendly vacation in Key West!Read more
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Trip Planning
breakfast in key west

Best Breakfast in Key West

Key West is a fantastic place for a getaway, whether you’re here with friends or family, out on a romantic retreat, or having a solo adventure all your own. There’s no shortage of things to do in Key West, from exploring historic sites like the...Read more
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Trip Planning
duval street key west

Our Elite Duval Street Shopping Guide

Explore all the very best shopping near Duval Street! Then, when searching for the perfect hotel near Duval Street, stay here with us at Dwell Key West.Read more
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Trip Planning
higgs beach key west 3-day itinerary

Our Thrilling 3-Day Key West Itinerary

Key West is an exciting destination no matter how much time you get to spend here! Planning a 3-day itinerary is perfect for a long weekend when you only have a few days to get away. Whether you plan on heading out on a President’s...Read more
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Trip Planning
halloween party

Best Things to Do in Key West During Fall

Key West, the southernmost point of the United States, is a tropical paradise that lures visitors year-round. While summer brings the sun worshippers and winter the snowbirds, the fall season offers a unique and enchanting charm of its own. As the island settles into a...Read more
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Trip Planning
key west mallory square

Start Planning Your 2026 Key West Spring Break Trip

You've never had better vibes than in Key West during Spring Break so now is the time to start planning your 2026 Key West Spring Break trip. Key West is full of adventure, culture, and laid-back luxury, making it the perfect destination for the ultimate...Read more
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Trip Planning
destination for a romantic honeymoon key west

Plan Your Ultimate Key West Honeymoon

With picturesque shorelines, entertaining nightlife, outdoor activities, and plenty of events and festivals, Key West is a great option for a honeymoon. Let’s plan your ultimate Key West honeymoon now!Read more
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Trip Planning

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