A Touch of Bermuda


Cottage, 2 Bedrooms, 2 Baths, (Sleeps 2-6)

Picture 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 townhome (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 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 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 educational 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 this vacation home 'A Touch of Bermuda in Key West'.

The bedroom configuration is the best. The master bedroom suite with a very comfortable king bed is upstairs with twin sinks, walk in shower and a reading area and separate from the downstairs bedroom with its two large Tommy Bahama twin beds and full bathroom. Both parties have great privacy by not sharing one 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.

This vacation cottage is fully equipped for an enjoyable stay.  The towels are thirsty.  The sheets of the highest thread count.  And all the small touches are there.  Hair dryer;. beach chairs; a complete kitchen with spices, coffee filters, blender and all the expected appliances.  The very large clothes washer and the dryer will make it easy to dry the beach towels if you so choose.  The pool is 200+ steps out my back garden gate down a pebble path. The best beach in Key West, Ft. Zachary Taylor State Park is within walking and biking distance and I have a beach pass for your stay. The famed sunset xelebrations at Mallory Square are short walk away as are the many tourist attractions such as Hemingway House; Harry Truman Little White 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.boardwalk within walking distance of my cottage.

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 and a little over a block away. I recommend a number of restaurants in the information kit I send you before you come down.


  • 2 Bedrooms, Sleeps 6


  • 2 Full Bathrooms


  • Downtown
  • Near The Ocean


  • Adventure
  • Attractions
  • Tourist Attractions
  • Sports & Activities
  • Historic
  • Family
  • Romantic


  • Catering available


  • Towels Provided
  • Clothes Dryer
  • Gated Parking
  • Iron & Board
  • Heating
  • Air Conditioning
  • Parking Off Street
  • Linens Provided
  • Living Room
  • Washing Machine
  • Wireless Internet


  • Coffee Maker
  • Microwave
  • Pantry Items
  • Dishwasher
  • Cooking Utensils
  • Dishes & Utensils
  • Stove
  • Refrigerator
  • Catering Available
  • Oven
  • Toaster
  • Ice Maker
  • Blender


  • Dining Area
  • Dining
  • Comfy seating for 6 people
  • Child High Chair


  • Television
  • DVD Player
  • Toys
  • Cable
  • Books
  • Video Library
  • Games
  • CD Player


  • Balcony
  • Deck / Patio
  • Garden


  • Couples
  • Family


  • Heated Pool
  • Communal Pool


  • Massage


  • Festivals
  • Health/beauty spa
  • Museums
  • Restaurants
  • Live theater
  • Playground
  • Botanical garden
  • Synagogues
  • Marina
  • Library
  • Cinemas
  • Churches
  • Arboretum


  • Photography
  • Wildlife viewing
  • Shopping
  • Boating
  • Scenic drives
  • Bird watching
  • Eco tourism
  • Antiquing
  • Walking
  • Sight seeing
  • Snorkeling
  • Sunset cruises
  • Dolphin cruise
  • Fine dining
  • Art galleries
  • Massage


  • Medical services
  • Massage therapist
  • Babysitter
  • Hospital
  • Groceries
  • Fitness center
  • ATM/bank


  • Diving
  • Swimming
  • Sailing
  • Cycling
  • Fishing
  • Golf
  • Wind-surfing
  • Paragliding
  • Tennis
  • Pickleball
  • Deepsea fishing
  • Hiking
  • Jet skiing
  • Pier fishing
  • Snorkeling
  • Basketball court
  • Kayaking
  • Parasailing


  • Ceiling Fans, Hair Dryer, Blender, Coffee Grinder, Spices, Coffee Maker, Toaster, Iron & Board, Lobster Pot and a popcorn maker.
  • Beach chairs


Rate Period Date From Date To Min. Stay Nightly Weekly Monthly
Spring / Summer / Fall 1st June, 2020 19th October, 2020 7 Nights min stay - $2,250.00 $7,500.00
High Season 27th October, 2020 30th May, 2021 7 Nights min stay - $2,450.00 $8,900.00
My Standard Rate - - 7 Nights min stay - $2,450.00 -

Additional information about rental rates

Damage Deposit : $350.00 which is refundable
Damage Protection Fee : The Security Fee Included
Cleaning Fee: Included in the rental fee
Pet Fee: $50.00
Tax: 12.5%


A refundable deposit takes property off the rental market. The rent itself is due 60 days before you arrive.
You can pay either through Pay Pal or by personal check.
The cleaning fees are included in the rental price.   If there is excessive cleaning needed such as from pets, I take the additional charges by my housekeeper from the deposit.
Most rentals must be between a Saturday and Saturday or else I lose an entire week of being able to book.  Exceptions are special events like Fantasy Fest; MOTM and Boat Race in November.

Manager's cancellation policy:

Heaven forbid but if a mandatory evacuation is ordered for in incoming hurricane, I will give you a credit for any unused days towards a future stay. Your security/property damage fee will be rolled over to your future visit..

Personal emergencies happen to all of us so if a guest has to cancel before 60 days, the rrent is returned and just the deposit is forfeited.   If cancellation happens within 60 days of arrival, the rent is refunded when a comparable booking is received.  The deposit is forfeited.

The truth is I am not some faceless corporate rental company so everything can be discussed.

Check Availability

Lura P.

Lura P.

A Touch of Bermuda is a Wonderful Cottage

My husband, George (our beagle) and myself absolutely loved this cottage. It was clean, well decorated and exactly the way Jack described it. We had everything that we needed. It was a pleasure to meet Jack and felt that we made a new friend when we left. We plan on renting this cottage again next year.
Philip L

Philip L

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!
Virginia S

Virginia S


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!


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.
Debra D

Debra D

Ideal place to vacation in Key West; exactly what we needed

We truly enjoyed our stay in the cottage. My husband had business in Key West, so it worked out great for us. The cottage is located within a short walking distance to restaurants, entertainment, and so many tourist attractions. It made the stay so much more enjoyable. The cottage is very nice and provided everything we needed. The beds were very comfortable and having the extra bathroom made it convenient for our son who traveled with us. We are so appreciative of Jack, the owner. He was readily available to answer any questions or help in any way he could. We highly recommend staying here for your next Key West vacation.
Jack A.

Jack A.

Best Amenities, Location and Host

My review title says it all. Little nicities like a pass to the nearby Ft. Zach beach which is in walking distance. ; two block walk to Duval St and a very responsive owner. You won't be sorry to stay here.
Robert E.

Robert E.

Fantastic place to stay in Key West

Jack’s place was perfect for our group of 5. Spacious, comfortable, beautifully decorated and in an ideal location. Jack was a pleasure to do business with and to get to know. Looking forward to a return visit.
Alicia P.

Alicia P.

Family Retreat

I absolutely loved this home and the area. When we first arrived there were little issues, but the owner and staff were on top of it and got it all resolved quickly. It was clean and very inviting. I will definitely stay here again in the future!!!

Steven H.

Steven H.

Location, location! Quiet retreat, yet close to everything.

Great location in Truman Annex, beautiful area for any outdoor activity including quiet sunsets. Family and pet friendly with open parks, beach access, pool area. Quiet, yet in the heart of Key West. Close to great food and plenty of entertainment. A most pleasureable experience from booking, planning, to exiting. Looking forward to future trips.

S J.

S J.

Slice of Heaven in Key West

The location in Key West is perfect for walking to restaurants, shopping, and the beach. The Truman Annex is truly the best location in Key West, with Duval only 2 blocks away. The owner was very easy to work with, and quickly answered any questions we had. The cottage had a great layout with plenty of privacy & comfort. Beautiful garden, great location and safe environment makes the perfect spot! We hope to return in the not too distant future. Thank you ... Jack for sharing your piece of paradise with our family!
Lee T.

Lee T.

Great property in a great location!

This was our first trip to Key West in many years and this year, we took our two five-month old French Bulldogs for their first road trip and breach trip. The property in the Truman Annex provides convenient, walkable access to all the sites in Old Town as well as the Truman Waterfront Park. This park, only two blocks from the house, was a great space to walk and run our frenchies with other dogs and their humans. The house was fully stocked with all our practical needs and provided ample space for the two of us and our fidos. Jack, the proprietor, made sure that we had clear check-in directions and was flexible with our late check-in time. He touched base occasionally to see if we needed anything and was only a phone call or text away. I recommend this property for a visit to Key West, especially with pets.
Ella K.

Ella K.


Everything was Great!!! We enjoyed our stay in Key West. Jack was very Hospitable It was very centrally located. I definitely would stay here again if I ever visit Key West again.