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.

blue haven pool

Complete Guide to Key West vacation rentals offering luxury poolside amenities

For those eyeing the island lifestyle at a relaxed pace, consider an extended-stay vacation home with a private pool and special amenities in tropical Key West! Historic Key West Vacation Rentals offers many deluxe homes with especially luxurious poolside amenities for the ultimate tropical retreat...Read more
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Key West Vacation Guide
the pink house pool

Embrace valuable family time in Key West with a poolside extended vacation rental

Dreaming of taking your family on an extended vacation in the beautiful, sun-soaked paradise of Key West? Consider a family-friendly rental that offers extra space and a private pool. At Historic Key West Vacation Rentals, we know that a comfortable, well-equipped space is top of...Read more
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Key West Vacation Guide
california dreaming pool

Luxury Vacation Rentals with Private Pools: Your Key West Getaway

Imagine stepping into your own tropical oasis — a private pool surrounded by lush palm trees, the sound of water gently rippling, and the warm Florida sun overhead. For travelers seeking more than just an escape, a luxury vacation rental with a private pool in...Read more
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Key West Vacation Guide
key west aerial shot

Florida Keys Overseas Highway: Cross 37 Iconic Bridges

The Florida Keys Overseas Highway is more than just a scenic drive—it's a journey steeped in history, engineering marvels, and unparalleled natural beauty. Stretching 113 miles from Key Largo to Key West, this highway is one of the most famous roadways in the world. Built...Read more
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Key West Vacation Guide
la casita

Your Guide to Old Town Key West

Imagine stepping into a tropical paradise filled with vibrant colors, rich history, and the rhythmic charm of island life. Welcome to Old Town Key West—a place where every street corner has a story to tell, and every home whispers of times past. Covering just 5...Read more
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Key West Vacation Guide
cloud 9 wood doors

Guide to Rentals in Key West, FL Near Duval Street

Planning a trip to Key West? Choosing the perfect place to stay is essential to maximizing your experience on this vibrant island. For those who want to be at the heart of all the action, there’s no better location than staying in rentals near Duval...Read more
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Key West Vacation Guide
azur palm beach

Beachfront Rental Homes in Key West

Dreaming of a toes-in-the-sand vacation in the tropics? How about sipping an umbrella-studded drink and gazing out to sea from the comfort of your own terrace? Or being lulled to sleep each night by the rhythm of the sea? Historic Key West Vacation Rentals has...Read more
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Key West Vacation Guide
fantasy fest 2024

Key West Fantasy Fest 2024: Ultimate Guide

Key West Fantasy Fest 2024 is right around the corner, and it’s shaping up to be one of the most vibrant and unforgettable events of the year! Held annually in October, Fantasy Fest is a 10-day celebration that transforms the island into a hub of...Read more
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Key West Vacation Guide
key west santa

Christmas Events in Key West

Your Guide to a Tropical Holiday Celebration If you're searching for a tropical twist to your holiday season, look no further than Key West. With its warm weather, festive lights, and unique island charm, Key West is the perfect escape from traditional snowy winters and...Read more
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Key West Vacation Guide
christmas key west

Christmas in Key West FL

A Festive Celebration with a Tropical Twist If you're seeking a holiday season like no other, look no further than Christmas in Key West FL . Imagine twinkling lights wrapped around palm trees, Santa trading his sleigh for a jet ski, and tropical breezes replacing...Read more
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Key West Vacation Guide

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