Key West Vacation Guide

Key West is a VERY dog-friendly town! Furry friends are even allowed in some bars and restaurants on our island. There are also several dog parks and even a dog beach! If you wish to travel with your dog(s), we do have dog-friendly vacation homes available.

La Casita en Cima- NEW Monthly Rental

Your Key West Vacation Starts Here

Dreaming of a sun-soaked getaway where you can experience the best of island life? Look no further than Key West, a picturesque island that offers everything from stunning sunsets to rich history and exciting activities. Nestled at the southernmost point of the United States, Key...Read more
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Key West Vacation Guide
key west events

Top Key West Festivals of Late Summer & Fall

Rich in natural beauty, colorful history, vibrant culture, unique architecture and bustling nightlife, there are many reasons visitors flock to Key West. Add this to the list: Key West knows how to throw a party, with countless events scheduled each year to celebrate just about...Read more
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Key West Vacation Guide
Three Arches

Discover Key West Architecture

A Rich Tapestry of Key West Architecture Styles Conch Houses: Iconic and Historic Key West’s Conch houses are a testament to the Florida keys rich architectural history. Dating back to the early 19th century, these homes blend Caribbean and American styles. Conch style houses are...Read more
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Key West Vacation Guide
Key West Walk

Key West Walking: Soak in the Sights

There are many ways to explore the paradise that is Key West, but our island’s compact, pedestrian-friendly layout makes the southernmost city in the continental U.S. an ideal destination for walking. A leisurely stroll reveals the island’s charming hidden streets, rich history and fascinating natural...Read more
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Key West Vacation Guide
Charter Fishing Key West

Experience the Ultimate Key West Fishing Vacation

Ready for the ultimate Key West fishing vacation? Look no further! Historic Key West Vacation Rentals offers the perfect launch pad for your fishing adventures in paradise. With convenient locations, ample storage for your gear, and relaxing amenities, our vacation rentals are the ideal choice...Read more
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Key West Vacation Guide
key west transportation options

The Best Ways to Get Around in Key West FL

While Key West lives large in the minds of those seeking a fun-filled, tropical adventure, the city itself is quite small, measuring just about 4 miles long and 1 mile wide. And that means there are varied transportation options that do not involve an automobile...Read more
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Key West Vacation Guide
key west golf cart

Your Go-To Guide for Key West Golf Cart Rentals

Ah, Key West. The sun on your face, the wind in your hair … in a golf cart! It’s a local thing — a breezy and unique way to explore this tropical paradise. You’ll find it’s an incredibly convenient way to get around, as well...Read more
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Key West Vacation Guide
key west music scene

Where to Find the Best Live Music in Key West

No musician better embodied the “island escapism” aura and laidback lifestyle of Key West than the late singer-songwriter Jimmy Buffett. When he moved to our island in 1971, Buffett summed up his passion for his new backyard by writing “I Have Found Me a Home,”...Read more
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Key West Vacation Guide
key west beach

Key West Adventures

When it comes to stunning destinations that create unforgettable moments that live in your mind long after an Instagram post fades into digital obscurity, Key West tops the list. There's no place quite like it. Surrounded by the serene beauty of the Florida Keys, Key...Read more
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Key West Vacation Guide
key west independence

Celebrate Independence Day in the Conch Republic

In many ways, those who call Florida Keys home have always felt quite distant from mainland America. More than Key West’s remote location (literally closer to Cuba than Miami), the people here have long felt that their concerns were never fully recognised by the federal...Read more
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Key West Vacation Guide

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