Historic 1 BR/1 BTH waterfront cottage in prestigious Duck Key in the Florida Keys. Plenty of outdoor amenities including a 15 X 34 foot saltwater swimming pool, hot tub (available in winter), and grill with prep and dining area. The backyard perimeter is 95 feet of waterfront on a deepwater canal with a 50-foot concrete dock. The two-level dock is equipped with fenders, cleats, ladder and fish cleaning station. The upper level is ideal for mooring a boat and the lower level could be used for fishing or launching kayaks.
From the dock you can see the historic Truman Bridge and experience the fast tidal flow of water that passes through it. This is because Duck Key Developer Bryan W. Newkirk Sr. "made his canals through waterways so they could flush with the tidal changes." President Harry S. Truman dedicated the bridge April 2, 1964 and walked by and perhaps visited this home. The bridge that was built in 1955 was designed by Key West Artist Gene Otto in the style of venetian bridges in Italy.
As you walk across the more than 1/4 property, enjoy the tropical flowers and trees: banana, coconut, plumeria, and hibiscus. If you encounter a shower, you can relax under the covered porch or retreat indoors where multiple picture windows allow the tropical paradise to be viewed from the comfort of a rattan sofa.
When you walk into the cottage, you will be struck by the spacious airy feeling. This is created by the 9 foot ceilings and the view of the outdoors that can be seen from the granite kitchen island that opens up to the living room.
A lot of care was taken to save the historic features and flavor of Newkirk's one-of-a-kind creation. This cottage is one of the few remaining homes that Newkirk built on Duck Key. Originally called the "Villa Jamaica Cottage" in the 1956, it was styled after a British West Indian Isles cottage.
Otto also decided the theme for the first private residences that Newkirk built, including the Villa Jamaica Cottage. As instructed by Otto, these homes were built on a Caribbean theme with "earth-colored tile roofs, with wide overhanging eaves like so many older houses encountered at Key West, Jamaica and other Caribbean islands." Villa Jamaica, along with the other private residences that Newkirk built had the West Indian architecture.
In keeping with the Otto's original theme for the cottage, the restored home has a clay tile roof from Ludowici as was the original roof and the soft green painted exterior is the same color that was first painted on it. The earthy colored quarry tile floor was restored and the bathroom has the original tile and Ming Green American Standard bathroom tub, toilet and sink. The porch and front door steps have their original clay brick floor.
Also in keeping with the British West Indian Isles theme and original furnishings, the upgraded version of the "Villa Jamaica" has bamboo furniture and soft tones accented by colorful botanical upholstery and area rugs.
The living room has a rattan sofa and daybed and the bedroom has a king-size platform bed flanked by bamboo nightstands.
There are homes on the same street on Greeenbriar Road for rent too. If you have a larger group, they could rent one of those homes and you could enjoy your privacy at our cottage.
The closest boat ramp is at Hawks Cay Marina at 61 Hawks Cay Blvd in Duck Key. It is 0.4 miles from our cottage or 1 minute away. It costs $60 in and $60 out.
Security cameras are present outdoors for enhancing security when the home is not occupied. Your privacy will be respected during your stay. The cameras in the pool, hot tub and grill area will be turned off during your stay.
Registration Number: 2500018
Unique Benefits
When we first saw the cottage from the Truman Bridge, and watched and heard the water in the canal flowing by it, we knew this was where we wanted to be. The water rushing by the cottage sounded and looked like a river flowing by it. The cottage was the perfect size and we loved the fact that it sat on more than 1/4 acre. The cottage was just waiting for someone to love it and bring it back to its original charm. Once we were able to see the inside, we really liked having everything on one level and how well the space inside was designed.
Why Kids Love It
Swim in the 16 X 30 foot pool or sit and play on the pool's sun shelf.
Fish from the dock.
Watch marine life from the dock. You might even see a manatee or turtle swim by.
Interact with dolphins at Dolphin Connection in Hawks Cay only 3 minutes away.
See turtles at the Turtle Hospital in nearby Marathon.
Duck Key is an upscale community where owners take pride in their homes.
Dolphin Connection at Hawks Cay is 3 minutes or 0.5 miles away.
Sea Turtle Hospital is 19 minutes or 13.3 miles away.
SS Wreck and Galley Grill
Grassy Key Land and Sea Market
Sleeps 3: two adults and one child. A daybed is provided for a child. A kingsize bed is provided for mom and dad.
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Oct 10 2025 - Apr 30 2027 | $160 | $160 | $1,100 | $4,400 | 2 nights |
Fees:
Notes:
The weekly rate of $1100 is discounted. Less than one week is $160 per day.
When the 15 X 34 foot pool is heated, we do our best to keep the temperature between 78 to 82 degrees.
The hot tub is only available in the winter. Our pool and hot tub cleaner advised us to not fill up the hot tub until the temperature drops during the winter. She said it is too difficult to keep the chemicals balanced at a sanitary level in the hot tub when it is so warm outside.
Last updated on November 28, 2025
EDDIE A.PERFECT GETAWAY
THE LOCATION ON DUCK KEY WAS PERFECT FOR OUR TRIP. EXCELENT PROPERTY, EXACTLY AS ADVERTISED. IT WAS EVERYTHING WE WERE LOOKING FOR. GREAT POOL
Stayed: October 2025 Submitted: November 24, 2025
Host response
"Eddie, Thank you so much for your review. So happy you enjoyed your stay at our cottage. You and your wife Chris were perfect guests. We would love to have you back again. Blessings to both of you. Melinda and Greg"
Security cameras are present outdoors for enhancing security when the home is not occupied. Your privacy will be respected during your stay. The cameras in the pool, hot tub and grill area will be turned off during your stay.
The closest boat ramp is at Hawks Cay Marina at 61 Hawks Cay Blvd in Duck Key. It is 0.4 miles from our cottage or 1 minute away. It costs $60 in and $60 out.
The 15 X 34 foot pool can be heated for $75 a week upon request. We do our best to keep the pool temperature heated to 78-82 degrees.
When the outdoor temperature is warm, our pool cleaner advised us to not fill up the hot tub until the temperature drops. She said it is too difficult to keep the chemicals balanced at a sanitary level in the hot tub when it is so warm outside.
Member since 2018