Entire home·Private host

A Touch of Bermuda at Truman Annex

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Sun-loungers, beach towels - A Touch of Bermuda at Truman Annex (Key West)
TV, DVD player, books, video library - A Touch of Bermuda at Truman Annex (Key West)
Exterior - A Touch of Bermuda at Truman Annex (Key West)
Interior - A Touch of Bermuda at Truman Annex (Key West)
Exterior - A Touch of Bermuda at Truman Annex (Key West)
In the heart of Old Town, A Touch of Bermuda in Key West is a private townhome with gated entrance and 24-hour security. Unwind on the beach, pool or Duval Street with its many restaurants, shops and art galleries nearby. Enjoy high-speed internet connection, cable TV in both bedrooms and free reserved parking.

Reviews

9.8 out of 10
Exceptional

Entire home

2 bedrooms2 bathrooms111 sq m

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

A Touch of Bermuda at Truman Annex

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

Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Communal pool
  • Fenced private pool
  • Heated pool
  • Hot tub

Internet

  • Available in the cottage: WiFi

Parking and transport

  • Car not required
  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • TV with cable channels
  • Video library

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • Smoke-free property
  • Note from host: Feel free to smoke outside on deck & porch

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In the city centre
  • Near a health/beauty spa
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Bicycles
  • Boat
  • Golf
  • Heated pool
  • Kayak
  • Tennis
  • Water sports equipment
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby
  • Water skiing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Garden
  • Unit size: 1,200 square feet

Similar properties

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Deposit is refunded with the return of the beach p
No trucks, vans, trailers. hitches etc. are allowe

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
Note from host: Dogs yes. Cats &Porcupines no.

Children and extra beds

Children are welcome
Note from host: I have two daughters so my home is kid friendly

Events

No events allowed
This is my personal home.

Smoking

Smoking is not permitted
Feel free to smoke outside on deck & porch

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

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

Property is also known as

A Touch of Bermuda at Truman Annex Cottage
A Touch of Bermuda at Truman Annex Key West
A Touch of Bermuda at Truman Annex Cottage Key West

About the area

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. Visit our Key West travel guide
View more Cottages in Key West
Map
Key West, FL

What's nearby

  • Duval Street featuring signage
    Duval Street
    6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum featuring heritage elements and a house
    Ernest Hemingway Home and Museum
    6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park showing military items, heritage elements and interior views
    Fort Zachary Taylor Historic State Park
    8 min walk - 0.7 km
  • Mallory Square which includes a square or plaza, outdoor art and signage
    Mallory Square
    11 min walk - 1.0 km
  • Florida Keys National Marine Sanctuary
    5 min walk - 0.4 km

Getting around

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

Restaurants

  • Green Parrot Bar
    4 min walk
  • Willie T's
    6 min walk
  • Mangoes Restaurant
    7 min walk
  • Blue Heaven
    8 min walk
  • Rams Head Southernmost
    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).

How much is parking at A Touch of Bermuda at Truman Annex?

On-site parking is available at the property.

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 Truman Waterfront Park, Duval Street and Ernest Hemingway Home and Museum. Mallory Square and Fort Zachary Taylor Historic State Park are also within 15 minutes.

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A Touch of Bermuda at Truman Annex Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 40 out of 44 reviews
Rating 8 - Good. 3 out of 44 reviews
Rating 6 - Okay. 0 out of 44 reviews
Rating 4 - Poor. 0 out of 44 reviews
Rating 2 - Terrible. 1 out of 44 reviews

9.0

Cleanliness

10

Location

Reviews

10/10 Excellent

Thomas L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday Celebration

Great place to stay. Close to restaurants and other activities. i highly recommend.
Stayed 7 nights in May 2025

10/10 Excellent

Constance B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

More than just a touch of Bermuda

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.
Stayed 7 nights in Dec 2024

10/10 Excellent

Gail B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Little Bermuda in Key West is perfect!!

Great townhouse, wonderful location, clean, colorful, nice tropical feel and decor. Exactly as pictured and described!
Stayed 7 nights in Sep 2023

10/10 Excellent

Tina B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Get away

Had a great time, close to everything. Clean , roomy
Stayed 7 nights in Dec 2023

10/10 Excellent

Kris W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

LOVELY stay pre-Christmas at Bermuda cottage

perfect weather to walk the neighborhoods of Key West, with all the holiday lights shining! Truman annex is a safe walkable neighborhood, the condo had every amenity needed and located so close to the best Key West has to offer. Would highly recommend this property!
Stayed 13 nights in Dec 2023

10/10 Excellent

Gina R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Stay!

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
Stayed 7 nights in Jul 2024

10/10 Excellent

Sue J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved the location
Stayed 7 nights in Oct 2025

10/10 Excellent

thomas h.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was great
Stayed 7 nights in Jul 2025

10/10 Excellent

Leonard T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

It was great. Truly a wonderful week
Stayed 7 nights in May 2025

10/10 Excellent

Christine B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday Bash

Great time
Stayed 7 nights in Jan 2025

10/10 Excellent

Janie S., Missouri

Liked: Cleanliness, check-in, communication, location, listing accuracy

Trip to Key West!

A great location, great host and great property! We loved it!
Stayed 7 nights in Apr 2023

10/10 Excellent

Robert E., Henrico

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.
Stayed 7 nights in May 2018

8/10 Good

Karen D.

Liked: Check-in, communication, location, listing accuracy

Great location

Blocks from Duval
Stayed 7 nights in Jul 2023

10/10 Excellent

Carmella T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ladies Trip

Property was very nice. Needs a few minor updates but overall it was very nice.
Stayed 7 nights in Mar 2024

10/10 Excellent

Michelle N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay

This was the cutest cottage in the perfect location….close to everything, yet quiet and peaceful. Thank you Jack for thinking of everything. We enjoyed it.
Stayed 7 nights in Jul 2022

10/10 Excellent

Brooke T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tropical Paradise

We absolutely loved our time spent at Touch of Bermuda in Key West. Jack was great. Everything went so smoothly. We can’t wait to go back!
Stayed 7 nights in May 2023

10/10 Excellent

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!!!
Stayed 7 nights in Jun 2018

10/10 Excellent

Carl R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best Possible Location in Key West

The location in the Truman Annex cannot be better. It’s a short walk to most attractions in Old Town. Jack provided excellent communication to ensure a smooth vacation. The property is as presented in the listing photos.
Stayed 7 nights in Jun 2023

10/10 Excellent

Mike H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

40th Bday

We were in KW with a group to celebrate a 40th birthday. Everyone stayed a different place in Truman..it was great
Stayed 7 nights in Apr 2024

10/10 Excellent

Michael C.

Liked: Cleanliness, communication, location

Convenient to everything

Update check in time!
Stayed 7 nights in Mar 2023

10/10 Excellent

Michelle B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous property in excellent location.

Very quiet location yet only 2 blocks from Duval St and all the action and so many restaurants. Excellent privacy for couples vacationing together as one bedroom is upstairs and the 2nd is downstairs. This home has lots of amenities including a dishwasher, washer/dryer, and fully equipped kitchen with condiments. The Truman Annex is very walkable and peaceful with lush landscaping. The owner responded quickly to our questions and was very helpful.
Stayed 7 nights in May 2022

8/10 Good

tamara p.

Liked: Check-in, communication, location, listing accuracy

Great stay in key west

We had a nice time in key west staying in the cottage owned by Mr. Agnew (Jack). It is in a location that is close to everything. We rented bikes for the week and rode or walked everywhere, even to and from the grocery, chartering a boat for fishing and Smather’s Beach. It was nice to have air conditioning as a few days were warm toward the end of the stay. The cottage is older, but in good shape. We enjoyed the front porch, the back patio and the pool which was just down the path. We were glad to be just outside the hustle and bustle of Duval street but it was right there if wanting to shop, etc. Sunsets, ice cream, restaurants, museums, light house, fort Zachary Taylor + beach all a short walk or bike ride away! Perfect location.
Stayed 7 nights in Apr 2021

2/10 Terrible

Jesse C.

Liked: Location
Disliked: Cleanliness, listing accuracy

Very Disappointed

Jack was a very communicative owner. The problem is that the home was filthy. There was urine all around the base of both toilets, not to mention the toilet itself was dirty in the downstairs basement. The sinks were caked with grime. The sheets on the master bed were ripped, stained and wore out so badly they wouldn’t stay on the mattress. There was not any bedding for the pullout couch, and we were told there would be. The blankets we found were ripped with holes and stained. The doors, floors, bannister railing were black with dirt. The chairs on the back deck were covered in bird/lizard feces and the deck was dirty with broken boards. Several throw pillows had blood stains on them. The hammock in the pictures is literally rotting in the back yard along with other garbage. Also the owner let himself into the home while we were there. There was also an elderly neighbor who rang our doorbell at least once a day, multiple times to tell us to turn lights off. The owner was notified of the issues, but nothing was ever rectified. We were so disappointed. He seems like a nice man, but that home is not acceptable.
Stayed 7 nights in Apr 2023

10/10 Excellent

Verified traveller

Liked: Check-in, communication, location, listing accuracy

Key west vacation

Great place to stay
Stayed 7 nights in Jun 2025

10/10 Excellent

Jerry H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We'll be back!

Very well cared for cottage with island theme throughout. Location at Truman Annex entrance is perfect, 2 blocks from Duval Street, and reserved parking space is 30 steps from front door. There is scooter parking on Thomas Street within 30 yards for rentals. Just can't say enough about how well we liked this cottage.
Stayed 7 nights in Oct 2022