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A Touch of Bermuda at Truman Annex
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Reviews
9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 61200 sq ft
Popular amenities
Explore the area

Key West, FL
- Place, Florida Keys National Marine Sanctuary5 min walk
- Place, Duval Street6 min walk
- Place, Ernest Hemingway Home and Museum6 min walk
- Airport, Key West, FL (EYW-Key West Intl.)13 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
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
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
Add dates for prices
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
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
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
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.

Key West, FL
What's nearby
- Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
- Duval Street - 6 min walk - 0.5 km
- Ernest Hemingway Home and Museum - 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
Getting around
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
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 window9.0/10
Cleanliness
9.6/10
Check-in
9.8/10
Communication
10/10
Location
9.6/10
Listing accuracy
Reviews
Verified
15 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Oct 2025
Verified
10/10 Excellent
thomas h.
17 Aug, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
thomas h.
Stayed 7 nights in Jul 2025
Verified
10/10 Excellent
Leonard T.
17 May, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay
Leonard T.
Stayed 7 nights in May 2025
Verified
10/10 Excellent
Thomas L.
4 Jun, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Birthday Celebration
Thomas L.
Stayed 7 nights in May 2025
Verified
10/10 Excellent
Constance B.
21 Dec, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
More than just a touch of Bermuda
Constance B.
Stayed 7 nights in Dec 2024
Verified
10/10 Excellent
Christine B.
1 Feb, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Birthday Bash
Christine B.
Stayed 7 nights in Jan 2025
Verified
10/10 Excellent
Janie S.
8 Apr, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Trip to Key West!
Janie S.
Stayed 7 nights in Apr 2023
Verified
10/10 Excellent
Robert E.
21 May, 2018
Fantastic place to stay in Key West
Robert E.
Stayed 7 nights in May 2018
Verified
8/10 Good
Karen D.
16 Jul, 2023
Liked: Check-in, communication, location, listing accuracy
Great location
Karen D.
Stayed 7 nights in Jul 2023
Verified
10/10 Excellent
Gail B.
23 Sept, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
A Little Bermuda in Key West is perfect!!
Gail B.
Stayed 7 nights in Sep 2023
Verified
10/10 Excellent
Tina B.
13 Dec, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Get away
Tina B.
Stayed 7 nights in Dec 2023
Verified
10/10 Excellent
Michelle N.
10 Jul, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent stay
Michelle N.
Stayed 7 nights in Jul 2022
Verified
10/10 Excellent
Kris W.
25 Dec, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
LOVELY stay pre-Christmas at Bermuda cottage
Kris W.
Stayed 13 nights in Dec 2023
Verified
10/10 Excellent
Carmella T.
24 Mar, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Ladies Trip
Carmella T.
Stayed 7 nights in Mar 2024
Verified
10/10 Excellent
Alicia P.
11 Jul, 2018
Family Retreat
Alicia P.
Stayed 7 nights in Jun 2018
Verified
10/10 Excellent
Brooke T.
31 May, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tropical Paradise
Brooke T.
Stayed 7 nights in May 2023
Verified
10/10 Excellent
Carl R.
27 Jun, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best Possible Location in Key West
Carl R.
Stayed 7 nights in Jun 2023
Verified
10/10 Excellent
Mike H.
7 May, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
40th Bday
Mike H.
Stayed 7 nights in Apr 2024
Verified
10/10 Excellent
Michael C.
4 Apr, 2023
Liked: Cleanliness, communication, location
Convenient to everything
Michael C.
Stayed 7 nights in Mar 2023
Verified
10/10 Excellent
Michelle B.
5 Jun, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous property in excellent location.
Michelle B.
Stayed 7 nights in May 2022
Verified
8/10 Good
tamara p.
26 Apr, 2021
Liked: Check-in, communication, location, listing accuracy
Great stay in key west
tamara p.
Stayed 7 nights in Apr 2021
Verified
10/10 Excellent
Gina R.
30 Jul, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent Stay!
Gina R.
Stayed 7 nights in Jul 2024
Verified
2/10 Terrible
Jesse C.
19 Apr, 2023
Liked: Location
Disliked: Cleanliness, listing accuracy
Very Disappointed
Jesse C.
Stayed 7 nights in Apr 2023
Verified
10/10 Excellent
Verified traveller
1 Jul, 2025
Liked: Check-in, communication, location, listing accuracy
Key west vacation
Verified traveller
Stayed 7 nights in Jun 2025
Verified
10/10 Excellent
Jerry H.
23 Oct, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
We'll be back!
Jerry H.
Stayed 7 nights in Oct 2022
About the host
Hosted by Jack Agnew
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
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