A Touch of Bermuda at Truman Annex - Key West Vacation Cottage Rentals


Home Description

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 home 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 a beach pass for your entire group to the Ft Zachary Taylor State Park beach?.

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

We know you will enjoy 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 sit 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 relaxing 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 and I have a beach pass for your stay. 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.

Come on down.

About The Area

The Truman Annex is in short walking distance to just about everything you want to see or do.   Duval Street is two blocks away.  The Ft. Zach beach is 880 yards away.  You name it....restaurants, attactions, fishing, boating, snorkeling, sight seeing, artistic endeavors (theater, art work, classes, lectures, film,) are all an easy walk.  Come on down.  We escaped Irma's wrath so you will not miss a thing.

House Rules

If this is a rule, so be it. Please don't make my home Party Central.  This is my personal abode so I appreciate your treating like your home away from home.


Romance.  Family.  Fisherman.  Artists,  grourmets, goumands,sunbathers and snorkelers.  My cottage is suitable for all.


Room Details

Sleeping Arrangements

Bathroom Arrangements

Calendar Last updated Jun 07, 2018
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A+ Location and Owner!

We thoroughly enjoyed our time in Key West, especially because of the wonderful location of the Bermuda House! Key West is quite compact, making it easy and fun to explore, and find new sights and history every day. We took a sunset cruise on America 2.0. The crew is capable, fun, and hospitable. We highly recommend an America 2.0 cruise as a must do for visitors that enjoy being on the water. Ft. Zachary Taylor Park is also beautiful, probably the best beach in Key West! Overall, we enjoyed the location and amenities of the Bermuda House very much. The location is A+ and the perfect place to immerse yourself in all that Key West has to offer. We parked our car and walked everywhere. Bermuda House welcomed us "home" from all day explorations to rest and rejuvenate. And because our plans were rather "last minute," the owner made the reservation process even more of a breeze. We hope we can return to Key West and the Bermuda House soon!

Visited on "January - 2017


We can't say enough about our vacation in Key West and our stay at the Bermuda House. It was truly amazing. The condo was absolutely beautiful, clean and in an great location. Through the rental process the owner was kind, friendly and extremely informative. We cannot wait to return to to the Bermuda House and to paradise!

Visited on "June - 2016

Amazing Owner

Whenever I book something through a website like this I always wonder if I am going to get what is advertised and if the owner is trustworthy. Unfortunately I cannot comment on the property since I had to cancel my trip but the owner of his property is absolutely amazing. From the very beginning he was responsive with email and phone calls and very helpful in the booking process. There were 4 of us who were going to be going on this trip but sadly we had to cancel to do one of the people going getting deployed during our dates. When I explained the situation to the owner he was more than happy to refund the full deposit and all the rent with no charge. Without having stayed at his property I would highly recommend his property purely on his customer service and kindness. As soon as we are ready for a trip to Key West he will be the first person I contact. Thank you again for being so kind, understanding, and trustworthy.

Visited on "May - 2014

Quiet cottage, close to everything

Jack's "Touch of Bermuda" cottage in Truman Annex is great! It's just inside the entrance of Truman Annex near the guard shack. The home is clean and has all the amenities you need for a week-long stay, including washer/dryer. Jack goes above and beyond to make sure your stay is a memorable one, providing you with all kinds of information on things to do while in Key West. Secure wireless internet is provided, as well as cable TV. Jack provides a key to the community pool inside the Annex, as well as a pass to Ft. Zachary Taylor State Park, which is nearby. The upstairs master "suite" is very large and has a king bed, flatscreen TV and a chair. There is also a pack-n-play for little ones. Our 2.5 year-old daughter slept in it all week! On your first night, set the coffee pot to come on in the AM. Wake up the next morning to the smell of coffee and the sound of roosters crowing (chickens are everywhere in Key West). Sip your coffee on the front porch, enjoy the island breeze and watch the rest of the Annex come to life. Truman Annex is 2.5 blocks away from Duval Street, so you're far enough away from the noise when you want to relax, but close enough to the action when you want to go out. You're also 2 blocks from Blue Heaven and La Creperie - our two favorite breakfast venues. If you're physically able to ride a bike, rent bikes for your stay! You don't have to worry with parking your car, and you get to see so much more of Key West! By the way, Sunshine Bike Rental will take you to the airport at the end of the stay, free of charge. You won't be disappointed with "A Touch of Bermuda". It has all the comforts of home - but it's located in KEY WEST!!

Visited on "November - 2013

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