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.

life like a local

Live Like A Key West Local For A Month

Live like a Key West local for a month or longer so you can immerse yourself in our warm and tropical paradise and experience all that local living in Key West can offer. Discounts are often available for Key West monthly vacation rentals, especially in...Read more
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Key West Vacation Guide
Key West Life

Spend A Month In Key West

Our monthly luxury vacation rental homes in Key West are the perfect option for an extended stay in our tropical paradise. Immerse yourself in the warm and tropical paradise all month long and experience all that local living in Key West can offer. How to...Read more
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Key West Vacation Guide
chick a pea front porch

Luxury Key West Rentals Near Duval St

When you've been dreaming of your Key West getaway, you'll be glad you chose one of these four luxury Key West vacation rentals just steps from Duval Street. Location is key when you want to experience our Floribbean flavors of fresh seafood and fine cuisine,...Read more
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Key West Vacation Guide
cloud 9 pool

5 Best Key West Spring Retreats

While most are still dealing with colder weather, Key West is more than delighted to invite you to shovel sunshine. Spring in Key West is truly paradise. It's our delightful warmth and wonderful sunshine that create this twist that defies colder temperatures everywhere else. These...Read more
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Key West Vacation Guide
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

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