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The Studio at the Sa...
Petunia Cottage - sl...
Smuggler`s Den - His...
Harbour Lights Stud...


Smuggler's Den | 10 percent summer special

Summer in Key West

Leave the sweltering city sidewalks behind. Come learn why summer in Key West is the locals' best-kept secret. Tropical breezes, crystal clear water, great fishing, no crowds or lines, and a laid-back lifestyle. That's summer in Key West.

Let us help you get here: 10 percent off your first seven days of a monthly stay at Smuggler's Den, Petunia or Poppy.

10% off a One Month Stay - August and September at the Historic Sailmaker's House

Take 10% off a one month stay at the Historic Sailmaker's House - choose from the Sailmaker's Studio, The Treetop Apartment, or Harbour Lights Studio.  This property is 1 block from the Historic Seaport in Old Town and walking distance to everything!


Guest Reviews

"We stayed in Island Days July 25 - 29, 2013 and enjoyed our stay very much. The property was beautiful and exceeded our expectations...."
---Bobby A
"We obviously loved Banana Dream since we're renting it again. The condo was well furnished, and we especially liked sitting out on the ..."
---The Stein Family
"Island Days was a great experience. The home was very nice and clean, just as shown on the website. We were very comfortable and had ..."
More guest reviews >>


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.  For travelers seeking full-service accommodations, including housekeeping and chef services, we are able to offer a number of special services upon request.

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 personally provides information about every aspect of the travel and rental experience, including the minute details of what to expect at our breathtaking botanical gardens, quirky tours, or historic walking tours through lush gardens and homes neatly tucked away in Old Town.

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.