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A Touch of Bermuda at Truman Annex

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Welcome to our Bermuda-style cottage in the Truman Annex
There are just 8 cottages for rent in the Shipyard section of the Truman Annex
The walkway goes directly into the front door
Sit on the front deck and say hello to passebys on picturesque Southard St.
Just inside the front door you get the keys for the front/back door, pool & gate

Reviews

9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 61200 sq ft

Popular amenities

  • Hot tub
  • Pet-friendly
  • Dryer
  • Washer
  • Pool

Explore the area

View in a map
Key West, FL
  • Duval Street
    ‪6 min walk‬
  • Mallory Square
    ‪11 min walk‬
  • Southernmost Point
    ‪14 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪10 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

Other (See Description)

1 Double Futon

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area

About this property

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.
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Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
I have two daughters so my home is kid friendly
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Events

No events allowed
This is my personal home.
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Pets

Pets allowed: dogs (limit 2 total)
Dogs yes. Cats &Porcupines no.
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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

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Note from host: This is my personal home.
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

We should mention

A car is not required for transport to and from this property

About the area

Key West

Located by the sea, this cottage is in Old Town Key West, a neighbourhood 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. Travelling with kids? Consider USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Key West, FL

What's nearby

  • Ernest Hemingway Home and Museum - 6 min walk - 0.5 km
  • Duval Street - 6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 11 min walk - 1.0 km
  • Southernmost Point - 14 min walk - 1.2 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 15 min drive

Restaurants

  • ‪Willie T's - ‬6 min walk
  • ‪Santiago's Bodega - ‬6 min walk
  • ‪Aqua - ‬8 min walk
  • ‪Antonia's Restaurant - ‬6 min walk
  • ‪DJ's Clam Shack - ‬7 min walk

Frequently asked questions

Does A Touch of Bermuda at Truman Annex have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is A Touch of Bermuda at Truman Annex pet-friendly?

Yes, this property allows dogs (limit 2 total).

What time is check-in at A Touch of Bermuda at Truman Annex?

Check-in begins at 3:00 PM.

What time is check-out at A Touch of Bermuda at Truman Annex?

Checkout is at 10:00 AM.

Where is A Touch of Bermuda at Truman Annex located?

This family-friendly Key West cottage is located by the sea, within a 10-minute walk of We Cycle Key West, Duval Street and Ernest Hemingway Home and Museum. Mallory Square and Fort Zachary Taylor Historic State Park are also within 15 minutes.

About the host

Hosted by Jack Agnew

Host profile image
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.

Languages:

English