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.

key west aerial

Key West Vacation: Savor Summer in Tropical Paradise

Key West is the southernmost point of the continental United States — and worlds away from anywhere else a traveler can discover. A quintessential summer vacation destination offering a unique blend of natural beauty, vibrant culture and endless adventure, historic Key West offers something for...Read more
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Key West Vacation Guide
queen conch

Live life like a ‘conch’ through an extended stay at a Historic Key West Vacation Rentals home

Behold the queen conch — a species of large predatory sea snails that can be found along our shallow waters. This marine gastropod has become a symbol of the Florida Keys, particularly in Key West, with those born on the island referring to themselves as...Read more
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Key West Vacation Guide
key west blues

Find the ultimate ‘Blue Space’ in Key West

Sun-drenched, warm and carefree, Key West is renowned the world over as a languid vacation destination. Visitors here always seem to report a boost in mood and an enhanced outlook on life — and now science explains why. It all comes down to vitamin D...Read more
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Key West Vacation Guide
American restaurants Key West

Our 8 Favorite American Restaurants | Key West

Key West is the southernmost point of the continental United States with a foodie culture that's influenced by Caribbean, Southern and Latin American flavors. With ready access to fresh vegetables and seafood, especially our signature pink shrimp, traditional and fusion cuisine can be found all...Read more
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Key West Vacation Guide
Copa Cabana

Your Ultimate Guide to Key West In The Summer

Summer in Key West showcases a tropical paradise at its peak. The island city, famed for its laid-back atmosphere and rich history, transforms into a bustling hub of outdoor activities, cultural festivals and water sports. This guide will take you through everything you need to...Read more
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Key West Vacation Guide
Truman Annex

5 Best Things about Truman Annex Key West FL

Nestled in the charming city of Key West, the quaint and historically rich neighborhood of Truman Annex beckons visitors with its unique blend of tranquility, beauty and fascinating history. Whether you're a history buff, a sun-seeker or simply in need of a picturesque escape, Truman...Read more
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Key West Vacation Guide
conch indepence

42ND ANNUAL CONCH REPUBLIC DAYS

Fans and friends of the Florida Keys’ Conch Republic can celebrate the irreverent "nation's" 42nd birthday with activities including a tall ship pirate adventure, traditional shrimp boil, sunset boat parade, tour of the USCGC Ingham floating maritime museum, reenactment of the Great Sea Battle of...Read more
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Key West Vacation Guide
key west seaplane

Key West Day Trips

What's not to love about day trips during your vacation stays in beautiful and historic Key West? You're on vacation, so no one wants to lug around luggage, overstuffed bags, and all the other paraphernalia our overworked minds tell us we must have any time...Read more
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Key West Vacation Guide
remote work from key west

The Best Work from Vacation Home Rentals in Key West

The best Work From Vacation Home Rentals in Key West can be found within the luxury collections of Historic Key West Vacation Rentals. We feature home offices and amenities that will help your nightly, weekly, and month-long stays feel like home. Even though workplaces are...Read more
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Key West Vacation Guide
key west autumn

Key West's Tranquil Autumn Vibes

It may stil feel like summer in Key West, but just know fall is here. Our Conch Republic has all things delightful and frightful for munchkins, monsters, pumpkin eaters and masqueraders alike. You can unlock the fall magic by being as adventurous as you like...Read more
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Key West Vacation Guide

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