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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 6111.5 sq m

Popular amenities

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

Explore the area

Map
Key West, FL
  • Duval Street
    ‪6 min walk‬
  • Ernest Hemingway Home and Museum
    ‪9 min walk‬
  • Mallory Square
    ‪11 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪15 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.

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.

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

Property manager

Jack Agnew

Languages

English

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
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

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

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

  • Duval Street - 6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Mallory Square - 11 min walk - 1.0 km
  • Fort Zachary Taylor Historic State Park - 11 min walk - 1.0 km
  • Southernmost Point - 16 min walk - 1.4 km

Getting around

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

Restaurants

  • ‪Margaritaville - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Bourbon Street Pub - ‬8 min walk
  • ‪Mangoes Restaurant & Island Cuisine - ‬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.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 35 out of 39 reviews
Rating 8 - Good. 3 out of 39 reviews
Rating 6 - Okay. 0 out of 39 reviews
Rating 4 - Poor. 0 out of 39 reviews
Rating 2 - Terrible. 1 out of 39 reviews

9.2/10

Cleanliness

9.6/10

Check-in

9.8/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

10/10 Excellent

Leanne L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Mar 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

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

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

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

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

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

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

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

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

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

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

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

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

Michael C.

Liked: Cleanliness, communication, location

Convenient to everything

Update check in time!
Stayed 7 nights in Mar 2023

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

10/10 Excellent

Kay P.

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

Great house!

Great house in an awesome location!
Stayed 7 nights in Jul 2022

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

Daniel P., Fort Myers FL

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

Key West Vacation

Great location and nice home. Jack was very communicative.
Stayed 7 nights in Jun 2022

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

10/10 Excellent

Timothy M.

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

Great stay in KW

Had a great stay this March in Key West. A great part of that was staying in Jack's cottage. Extremely comfortable for four people. Location was very central to everything in Old Town but far enough off Duval to cut down on the noise. Jack was a gracious host and well versed in all things Key West. Hope to get back some day.
Stayed 14 nights in Mar 2022

10/10 Excellent

Sara M., Iowa

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

Absolutely Lovely!

We can't wait to stay here again. The location is superb to everywhere we go. Communication and responses from Jack were wonderful, everything we needed was in the house, we have zero complaints. Book it!
Stayed 7 nights in Oct 2021

10/10 Excellent

Jim D.

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

Great place and location to stay in Key West

Charming little house. Great for 4 people, 6 adults was a little more crowded. Master bedroom and bathroom are large. Outdoor spaces and neighborhood safe, well kept and attractive. Perfect location for walking to all the tourist spots, shopping and restaurants in old town. Secured parking for 1 car came in very handy. Would stay here again. Owner communicated well and was very helpful.
Stayed 9 nights in Sep 2021

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

10/10 Excellent

Debbi L.

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

Loved our stay!

Jack's property was the perfect location to what Key West has to offer. The property owner, Jack stopped by and was fun to talk to. We loved sitting on the front porch at night and the closeness to Duval, the State Park and walking around in Key West.
Stayed 7 nights in Apr 2021

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