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.

azur palm pool

Luxury Key West Monthly Snowbird Rentals

Four of our most luxurious Key West Snowbird Vacation Rentals for 2023/2024 are fully furnished premier homes that are perfect for long-term month stays in Key West , winter vacations and remote working assignments. In fact, our luxury vacation planners are dedicated to matching ideal...Read more
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Key West Vacation Guide
key west christmas tree

Key West Winter Rental Savings

Happy Holidays to you! Historic Key West Vacation Rentals is proud to announce seven opportunities for seasonal savings in December 2022. We've lowered the rates of all of our remaining Key West monthly rentals through the end of the year. Key West's mild weather means...Read more
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Key West Vacation Guide
potters cottage pool dining

3 Best Places For A Key West Thanksgiving

Come and dine. It's turkey time! The holidays are all about spending quality time with family and friends and Historic Key West Vacation Rentals wants to help take some of the stress out of entertaining. Why worry about whose home should host your holiday gatherings...Read more
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Key West Vacation Guide
Bahari House Work Remote Office

Luxury Vacation Rentals To Work Remotely In Key West

Work remotely in Key West and live like a local while doing your best at your dream job. No commute. No lunch rush. No travel costs. Save time for a better life filled with adventures that will make you a better employee. You'll have better...Read more
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Key West Vacation Guide
fantasy fest

Fall Savings For Fantasy Fest

Enjoy our new fall savings for Fantasy Fest October 21-30, 2022. We've lowered the nightly rates for our remaining luxury vacation rentals and we invite you to be our guests this festival season. Cult Classics and Cartoon Chaos is the theme for this year's 10-day...Read more
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Key West Vacation Guide
magical margaret

Introducing Magical Margaret

Introducing Magical Margaret, the newest Key West monthly rental to join our luxury vacation rentals collection. It's available for your fall and winter vacations beginning November 2022. As you enter the main home you will be captivated by the high-end kitchen, natural light, and hardwood...Read more
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Key West Vacation Guide
miss sunshine parking

A Virtual Tour of Miss Sunshine

A virtual tour of Miss Sunshine is just the glimpse of one of the best places to stay on your Key West Vaction . Historic Key West Vacation Rentals' Key West Monthly Rentals are the perfect option for an extended stay in our tropical paradise...Read more
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Key West Vacation Guide
Dog on Beach - Pet Friendly Rentals

Guide to Traveling To Key West With A Dog

Traveling to Key West with a dog is one of the best ways to experience our laid-back lifestyle. This is a very dog-friendly town — some of our bars, restaurants, and parks even allow dogs!Read more
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Key West Vacation Guide
Miss Sunshine Monthly Rental

The 7 Best Snowbird Luxury Vacation Rentals

The seven best Snowbird luxury rentals in Key West are available through Historic Key West Vacations Rentals. They're the best because they're located in this tropical paradise surrounded by crystal blue waters separated from the high octane speed of life on the mainland. All laid...Read more
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Key West Vacation Guide
dreaming on duval

Fantastic Vacation Rentals For Fantasy Fest

Fantastic vacation rentals for Fantasy Fest are staged and ready to deliver your best Key West stays ever. This outrageous 10-day costuming and masking celebration features dozens of masquerade competitions, themed parties and other exuberant events. The 2022 theme is ‘Cult Classics and Cartoon Chaos!'...Read more
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Key West Vacation Guide

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