A Touch of Bermuda in Key West

neighborhood of Key West Vacation Rentals
from/per night $400
  • Sleeps 6
  • 2 Bedrooms
  • 2 Bathrooms
  • 1200 sqft.
  • Accessible


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 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 the water activities are also a short walk away. And value? How about free re...

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  • Balcony
  • Beach Chairs
  • Bicycles
  • Boat
  • Deck / Patio
  • Kayak / Canoe
  • Lawn / Garden
  • Outdoor Furniture
  • Porch / Veranda
  • Tennis
  • Water Sports Gear
  • Books
  • DVD Player
  • Games
  • Satellite / Cable
  • Toys
  • TV
  • Video Library
  • Air Conditioning
  • Bed Linens Provided
  • Dryer
  • Hair Dryer
  • Heating
  • Iron & Board
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Historic Home
  • Living Room
  • Parking
  • Blender
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Communal Pool
  • Heated Pool
  • Pool
  • Children welcome
  • Wheelchair Accessible
  • Activities / Restaurants Guide
  • Alarm Clock
  • CD Player
  • Child Highchair
  • Cooking Utensils
  • Dining Area
  • Freezer
  • Gated Entry
  • Outdoor Gas Grill
  • VCR

Location Info

Everyone seems to agree that Southard Street in the Shipyard section of The Truman Annex is THE best place to stay in Key West. Duval Street is two blocks away and the best beach in Key West, Ft. Zachary Taylor State Park is about 800 yards in the other direction. Everything you want to see or do is within an easy walk. NOTE: During this pandemic, my home is being cleaned and disinfected according to CDC standards.

Rates & Fees

Nightly rates range from $400.00 to $420.00

From To Minimum Stay Nightly Rate
2023-11-05 2023-12-23 7 nights $400.00
2024-01-01 2024-06-01 7 nights $420.00
2024-06-01 2024-10-19 7 nights $400.00


About Owner

I'm a semi retired guy who was in the television and marketing/public relations industry and is now a professional character actor/singer on stage and I teach Marketing and Public Relations at a university outside of Boston, MA every Fall. My oldest daughter was married here in Key West and it's a special place for me as I hope it will be for you. Year purchased: 2005


  • Suitable for Children

General Policies

PLEASE no smoking inside. It is immediately clear if someone has lighted up and my housekeepers have to spend lots of extra time which will be deducted from the security deposit.

House Rules

limited accessibility I can't officially call my home ADA approved but there are no stairs to get into the front door from the sidewalk and since there is a bathroom and bedroom on the ground floor, this can work for some handicapped persons.

Terms & Conditions

The cleaning fees are included in the rental price. If there is excessive cleaning needed such as from pets, I take the additional charges for my houskeeper from the deposit.

By Home Owner Association rules, guests must stay a minimum of seven nights usually from Saturday to Saturday.

Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.


(Based on 15 reviews)
- 08/31/2020 -

Wonderful Cottage

"My family of 4 stayed at Jack's amazing cottage and loved it! Everything we needed was there so it was super easy to just enjoy ourselves. The location couldn't have been better. Just a short walk to Duval Street and an easy scooter ride to the beach. The cottage was decorated nicely and was very comfortable for 4 people. Working with Jack was a pleasure and he had lots of tips for first time visitors. We would definitely stay there again and would highly recommend it if you're traveling to Key West! Thanks for everything Jack!"

Great stay

"Excellent as listed"

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!"

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."

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!!!"

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