Skip to main content

A Touch of Bermuda at Truman Annex

5.0
A Touch of Bermuda at Truman Annex in Key West, Florida, United States — photo 1
1 / 37
A Touch of Bermuda at Truman Annex in Key West, Florida, United States — photo 2
2 / 37
A Touch of Bermuda at Truman Annex in Key West, Florida, United States — photo 3
3 / 37
A Touch of Bermuda at Truman Annex in Key West, Florida, United States — photo 4
4 / 37
A Touch of Bermuda at Truman Annex in Key West, Florida, United States — photo 5
5 / 37

Vacation House in Key West

2 bedrooms·2 bathrooms·sleeps 6·1,200 sq ft
Jack Agnew

Hosted by Jack Agnew

7 years hosting

Wifi included

Internet access throughout the property.

Private pool

A pool is available to guests.

About this space

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 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 seven nights and all bookings are Saturday to Saturday except for special events such as boat race week and Fantasy Fest. Starting in 2026. I can only rent for a MINIMUM OF 28 NIGHTS (four weeks Saturday to Saturday)

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.
Keywords: Cottage; Townhome, vacation home Our prices include all fees. No hidden fees.

What this place offers

air conditioning
balcony
bed linens provided
dishwasher
garden or backyard
hot tub
internet wifi
iron ironing board

Minimum 3 night stay

Add your travel dates for exact pricing

Things to know

House rules

  • children welcome
  • no smoking
  • pets allowed

Safety & property

  • accessible parking
  • fire extinguisher available
  • service animal friendly

Cancellation policy


100% refund if you cancel at least 60 days before check-in.
50% refund (minus the service fee) if you cancel at least 30 days before check-in.
No refund if you cancel less than 30 days before check-in.


Damage and Incidentals
You will be responsible for any damage to the rental property caused by you or your party during your stay.


House Rules
Check in after 3:00 PM
Check out before 10:00 AM
Minimum age to rent: 25
Children
Children allowed: ages 0-17
I have two daughters so my home is kid friendly
Events
No events allowed
This is my personal home.
Pets
Pets allowed: dogs (limit 2 total)
Dogs yes. Cats &Porcupines no.
Smoking
Smoking is not permitted
Feel free to smoke outside on deck & porch
Deposit is refunded with the return of the beach p
No trucks, vans, trailers. hitches etc. are allowe

5.0 · 2 reviews

Overall rating

5
4
3
2
1

5.0

2 reviews

Cleanliness

5.0

Accuracy

5.0

Check-in

5.0

Communication

5.0

Location

5.0

Value

5.0

TL

Thomas L.

June 2025

Birthday Celebration

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

LT

Leonard T.

May 2025

Great stay

It was great. Truly a wonderful week

Where you'll be

Key West, Florida, United States of America

About the area Located by the sea, this cottage is in Old Town Key West, a neighborhood in Key West. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Traveling with kids Consider USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center. Be sure to check out the area's animals with activities such as game walks and birdwatching. What's nearby Ernest Hemingway Home and Museum - 6 min walk Duval Street - 6 min walk Fort Zachary Taylor Historic State Park - 8 min walk Mallory Square - 11 min walk Southernmost Point - 14 min walk Getting around Key West, FL (EYW-Key West Intl.) - 10 min drive Restaurants Santiago's Bodega - 2 min walk La Creperie - 3 min walk Bourbon Street Pub - 6 min walk Pinchers - 6 min walk DJ's Clam Shack - 6 min walk

Important Information

Check-in

03:00 pm

Check-out

10:00 am

Change-over

Minimum 3 Nights

Pets

Not allowed

Meet your host

Jack Agnew

Jack Agnew

2

Reviews

5.0

Rating

7 Years

Hosting

Response rate: 95%

Responds within a few hours

Speaks

About Jack Agnew

Hosted by Jack Agnew – Key West Cottage Rental. 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 in 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. Why they chose this property: I always had TAE (Truman Annex envy) when my two daughters and I were visitors and renters in Key West. I vowed I'd live here one day, and when I sold my public relations firm in 1999, I bought a small two-bedroom, one-bath condo, and five years later, this much larger two-bedroom, two-bathroom cottage. I am in Key West at least six months a year and rent out my home when I am not in town. What makes this property unique: A Touch of Bermuda in Key West is my 'friend with benefits' as everything I want to see or do is within walking or biking distance. You are in walking distance to the nearby Ft. Zach beach, and the new water splash pad for children is just down at the end of the block. One couldn’t ask for more.

  1. Message the host with your dates and questions.
  2. The host confirms availability, rates and rental terms.
  3. Agree the rental agreement and payment method directly with the host.
  4. Pay the host using their approved process — not through this site.

Find Vacation Home Rentals connects you directly with the host and does not process payments. Confirm rates, availability and the payment method with the host before you book.

Starting at$474/night