A Touch of Bermuda at Truman Annex

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private town home (one of only seven available for rent) in the Shipyard section of the Truman Annex with its gated entrance and 24 hour security. Our Bermuda-style cottage is steps away from sunning yourself on the beach, at the pool or enjoying the excitement of Duval Street with its many award winning restaurants, unique shops, creative art galleries, lively bars and bawdy night clubs. The famed Mallory Square and the water activities are also a short walk away. And value? How about free reserved and secure parking? High speed internet connection and cable tv in both bedrooms? By Condo Association rules, there is a minimum stay of seven nights. Guests come and go on a Saturday.

We also offer themed getaways for your honeymoon; anniversary; birthday or a week of romance.

We know you will enjoy building memories in our home as well as Key West. On my living room walls are paintings I have purchased in Cuba from my humanitarian and education trips to the island. The colorful and yet relaxing paint hues on the wall are from my visits to Bermuda which is why I call my vacation home 'A Touch of Bermuda in Key West'.

The bedroom configuration is the best. The master bedroom suite is upstairs and separate from the downstairs bedroom and bathroom. Both parties have great privacy by not sharing a bathroom between two bedrooms.

You will want to be outside much of the time so relax on my front porch facing picturesque Southard St. and say hello to your neighbors. Or for privacy, the very large back deck with comfortable chairs for reading and a dining table for six for a private dinner under the stars is just the ticket.

Pets by special permission. No short weekend stays. It's not permitted by home owner association rules.

The Truman Annex is a former Naval base in the heart of Old Town in Key West. President Harry Truman used to vacation here so this residential complex is named after him. There is a wonderful tour available in the home he used as his summer residence. Duval Street is two blocks away. The pool is 100+ steps out my back garden gate down a pebble path. The best beach in Key West, Ft. Zachary Taylor State Park is within walking distance. The famed sunsets at Mallory Square are short walk away as are the many tourist attractions such as Hemingway House; the Aquarium and Mel Fisher's Treasure Museum. And if water sports are your thing, the snorkel, scuba and fishing trips all start at the local pier within walking distance of my cottage.

Golf: There is an 18 hole golf course in Key West which is open to the public. It's not Pebble Beach or Augusta National but you can keep your game up to snuff by playing a new course. The links are within a short drive from my cottage but alas, this is one attraction not in walking distance. Good luck in breaking par.

Other Activities: Some really fine dining at award winning restaurants. On the walls of my living room, I have a painting of the Blue Heaven restaurant, one of my very favorites. It is quintessential Key West. MINIMUM OF ONE WEEK OR MORE STAY USUALLY SATURDAY TO SATURDAY due to Home Owner Association rules. ALAS, STARTING IN JANUARY OF 2026, THE CITY OF KEY WEST INTENDS TO DENY THE SHIPYARD SECTION OF THE TRUMAN ANNEX, THE RIGHT TO RENT BY THE WEEK. OUT OF RESPECT TO YOU THE VISITOR, I CANNOT ACCEPT ANY LESS THAN A MONTH LONG STAY (28 NIGHTS) STARTING IN JANUARY OF 2026. I HOPE THIS WILL CHANGE BUT FOR NOW I WILL NOT JEOPORDIZE YOUR RENTAL.

Unique Benefits

1. Privacy with each set of bedrooms and bathrooms on separate floors.
2. Reserved and secure parking
3. High speed WIFI
4. Cable TV.
5. Location. Mid way between the new Waterfront Park and Duval St.
6. Location You are on picturesque Southard St. to say hello to passersby while sitting on my front porch.
7. My cottage receives a deep cleaning following CDC guidelines.

Why Kids Love It

The new Waterfront Park has a Splash pad/water park for kids to get wet and play.
The Aquarium, Butterfly Expo, Shipwreck Museum and Mel Fisher's Treasure Museum are all wonderful to visit
The heated pool just steps out my back gate is very inviting.
The Ft. Zach beach is 800 yards away and has a snack bar, changing rooms and outdoor showers.

Area Information

The Truman Annex is a former Naval base that was closed and a developer built THE vacation community in Key West. Just about everything you want to see or do is within walking distance. I hope my photos speak for themselves and you can always go to my website to see more. Come on down.

Attractions Within Walking Distance

All of them. Hemingway House; Truman Summer White House; Butterfly Expo; Aquarium; Shipwreck Museum; Southernmost Point; Ft. Zach park and beach; Duval Street. There is no better location than my cottage.

Favorite Places To Eat

My personal favorite has been Blue Heaven for twenty five years but I could put down a list that would use all this space. In my information packet, I list my personal favorites but you may discover some place I have forgotten and you can remind me to update this listing.

Inside Scoop

You have to ask me for tips only locals know so I can get you to make an inquiry about my cottage.