A Touch of Bermuda at Truman Annex

Key West, Florida
$463 avg/night Minimum Stay 28 Nights
Bed 2

Bed

Bath 2

Bath

Home Cottage

Property Type

Sleep 6

Max Sleeps

Night 28 nights

Min Stay

MONTH STAYS ONLY 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 reserved and secure parking behind my cottage High speed internet connection and cable TV in both bedrooms .

We also offer themed getaways for your honeymoon; anniversary; birthday or a week of romance.
NOTE: I HAVE NICE OPENINGS IN THE SUMMER AND FALL. IT WOULD BE MY PLEASURE TO GIVE YOU A GIFT CERTIFICATE TO ONE OF KEY WEST'S BEST RESTAURANTS.
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 to enjoy a private dinner under the stars.

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 if you have little ones, the Splash Pad at the end of the street is a joy. 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 course the only one on the Keys. 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. Minimum stay is 29 days/28 nights and all bookings are Saturday to Saturday except for special events such as the boat races and Fantasy Fest.

PS If your party is small and you want another nice option for good value, check out my casita (condo) here in the Truman Annex # 1049465 on VRBO. I will let the amenities speak for themselves in my listing. It is located six doors away from my Touch of Bermuda cottage.
Keywords: Cottage; Townhome, vacation home

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    2 Total Pets Pet Friendly Welcoming Dogs Only
  • BEACH

    Beach Sun Loungers Beach Towels
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1200 Sq Ft (111 Sq M)
  • KITCHEN

    Blender Cookware/dishes/utensils Dishwasher Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Not Required Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Fenced Yard Garden Outdoor Furniture
  • POOL/SPA

    Fence Around The Pool Heated Pool Hot Tub Shared/communal Pool
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Boat On Site Ecotours Nearby Fitness Facilities Nearby Golf Nearby Golfing On Site Hiking Nearby Jet Skiing Nearby Kayak On Site Power Boating Nearby Sailing Nearby Scuba Diving Nearby Swimming Nearby Tennis On Site Water Sports Equipment Windsurfing Nearby
  • ENTERTAINMENT

    Books DVD Player Games Video Library TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Babysitting Service Available Children's Books Children's Games Children's Toys Highchair
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Note From Host: Feel Free To Smoke Outside On Deck & Porch Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Sue J.

    Submitted Oct 15, 2025

    Stayed Oct 5, 2025

    Loved the location

  • thomas h.

    Submitted Aug 17, 2025

    Stayed Jul 26, 2025

    It was great

  • Submitted Jul 1, 2025

    Stayed Jun 21, 2025

    Great place to stay

  • Thomas L.

    Submitted Jun 4, 2025

    Stayed May 17, 2025

    Great place to stay. Close to restaurants and other activities. i highly recommend.

  • Leonard T.

    Submitted May 17, 2025

    Stayed May 3, 2025

    It was great. Truly a wonderful week

  • Christine B.

    Submitted Feb 1, 2025

    Stayed Jan 18, 2025

    Great time

  • Constance B.

    Submitted Dec 21, 2024

    Stayed Dec 14, 2024

    I’ve always wanted to stay in the Truman Annex and this cottage did not disappoint! Clean, comfortable and you just cannot beat the location. Secure parking as well. I will definitely stay here again.

  • Gina R.

    Submitted Jul 30, 2024

    Stayed Jul 20, 2024

    The property is just as it's pictured and in a beautiful neighborhood. The location was amazingly convenient, a 5 minute walk or bike ride from everything. The bike rental place is on the same block, so very convenient to pick up and drop off. I almost did not use my car the entire time we were there. The house was comfortable for the 4 of us, plus our large Labrador dog. The host, Jack, was extremely kind and generous and always available if needed. He replied to my emails almost immediately every time. I would definitely rent this house again or any other property from Jack. I'm sorry I waited so long to do this with my family! We absolutely loved it and did not want to leave. We can't wait to come back. - Gina Rovetto & Family

  • Mike H.

    Submitted May 7, 2024

    Stayed Apr 27, 2024

    We were in KW with a group to celebrate a 40th birthday. Everyone stayed a different place in Truman..it was great

  • Carmella T.

    Submitted Mar 24, 2024

    Stayed Mar 16, 2024

    Property was very nice. Needs a few minor updates but overall it was very nice.

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Total

Includes taxes and fees
$463+
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