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“Stay a Week ~ Stay a Month ~ Stay a Lifetime”
Boutique Luxury Vacation Rentals

Historic Key West Vacation Rentals offers luxury, historic vacation rental homes in Key West, Florida. Our vacation specialists will guide you through the selection of the property that's perfect for your stay. Our staff is committed to offering a uniquely personal touch in helping plan ideal independent travel vacations. We are proud of our commitment to first-rate personal service and believe it sets us apart from the rest.

We appreciate that our guests are thrilled by the prospect of "living like the locals" in a luxury private home surrounded by delightful tropical settings. Staying in a private home is truly the only way to experience Key West. 

Working directly with our owners, we seek to create an atmosphere of hospitality that will make you feel instantly at home. Our owners take pride in offering historic, charming and comfortable homes that offer the relaxing Key West experience. 

Historic Key West Vacation Rentals makes it our business to find vacation rentals of the highest standards that go above and beyond our guest's expectations. By providing the finest experience in vacation rentals we ensure your vacation is one you will dream about for years after. Our team is dedicated to creating your ideal Key West vacation through friendly, efficient attention to every detail of the process.



Spend a month or more in Paradise and invite friends and family to visit during your stay!
Guest bedrooms, spacious interiors, refreshing pools, and great locations make our monthly rentals the perfect choice for your next adventure.

Work remote?  Why not live in paradise with the locals.  High Speed Internet available at all properties.   


Tropical Dream

Tropical Dream

Historic Old Town Meadows
Luxury Vacation rental house.
Sleeps 8
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Inn Cogneato

Inn Cogneato

Historic Old Town
Vacation rental house
Sleeps 5
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Historic Key West Vacation Rentals 425 Eaton Street Key West, FL 33040 (305) 296-1010

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