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Craig & Cindy's Truman Annex Key West Property

Bedrooms 2
Half Baths1
Property type house
Minimum Stay 7 nights

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Half Baths
Minimum Stay
7 nights

About the property

House, 2 Bedrooms + Convertible bed(s), 2.5+ Baths, (Sleeps 4-6)

We are Craig & Cindy and we thank you for inquiring about our Truman Annex Key West vacation homes. Truman Annex is ideally located in 'Old Town' Key West and is an easy walk to all the fun in Key West, from the Mallory Square Sunset Festival to Ft. Zach Beach to Duval Street (restaurants, nightclubs and shopping) to numerous museums.

As a former Navy Base, Truman Annex is obviously adjacent to the water. It is also a 'gated community' with its own private security and guard controlled gates. Due to its ideal location, a car is not necessary (though parking is available) and numerous bicycle and scooter rental locations are available should the need arise.

We love Key West and have been offering our rentals since 1995. We have a strong repeat guest list because we maintain our homes as our second homes and offer deluxe furnishings.

Keywords: Truman Annex, Private Home, Craig & Cindy, Key West, Old Town, Duval Street, Key West Rentals, Craig, Cindy, Florida, Mile Marker 0, Condo, Townhouse, Vacation

More Details

Member since: 2001
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
January 22, 2017

About The Owner

Craig & Cindy Key West Rentals have been offering rentals in Key West since 1995. We love Key West and consider it our second home and split our time between Key West and Cleveland, OH. We bought our first property in Key West in 1995 and started renting it help pay for the cost. We soon realized we had passion for owning and renting Key West vacation properties and began adding more properties. We currently have more than 12 homes and condos available for rent in Key West and have a great group of repeat guests! For more information see our personal Key West website at RentMyParadise or see Craig & Cindy Key West Rentals on Facebook for last minute specials and other Key West fun!

The Owner purchased this house in 2003

Why The Owner chose Key West

We love Key West and consider the Truman Annex the finest location on the island. This property is a gorgeous private home in the Truman Annex. Truman Annex is at Mile Marker 0 and is ideally located so that it is an easy walk to the beach, Duval Street, Mallory Square Sunset Festival and all that Key West has to offer.


Wonderful! 4.9/5 -
(7 traveler reviews)

Craig & Cindy's Truman Annex Key West Property
average rating of 4.857143 based on 7 reviews
Buffalo, NY

Booked our return visit for 2017!

  • 5 of 5

All the reviews about Craig & Cindy and their properties are spot on. We stayed at 214 and it is a beautiful house & perfect location. No matter which way you want to go, Mallory Square or Duvall St., you will be there in about 5 minutes. Very quiet, relaxing & private. Felt right at home immediately. The property is just as described and Craig & Cindy have thought of everything, the only thing we needed was food. Ladies as of August 2016 there were 2 hair dryers, Guys as of August 2016 there were 2 hair dryers! The cleaning staff does an amazing job and my wife wishes she could have brought them home with us. We did spot Fleming the Cat on our last day.

Please don't forget the packet they send you, it comes in quite handy for quick reference of codes, phone numbers and places to eat and play.

Thank you again for providing a great HOME on our vacation!

  • Submitted: Aug 11, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
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1 0

Location! Location! Location!

  • 5 of 5

Four of us stayed in the condo in January and found it to be very comfortable in every way. Beds were great, plenty of linens, & the washer and dryer were conveniently located by the bedrooms. We cooked in some and found the kitchen to be adequately furnished. We enjoyed the outside patio and used the grill on occasion. The best thing about the condo is the location. We walked or rode our bikes everywhere and never moved our car in the week we were there. Craig and Cindy were great to work with in every way. I highly recommend this condo if you are planning to stay in Key West!

  • Submitted: Feb 7, 2016
  • Stayed: Jan 2016
  • Source: VRBO, from HomeAway
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4 0

Clean and Beautiful

  • 5 of 5

As described.

I would recommend.

  • Submitted: Jun 9, 2014
  • Stayed: May 2014
  • Source: VRBO, from HomeAway
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2 0

Best in Key West

  • 5 of 5

We visit Key West every year and the Truman Annex is the place to stay. This is our second year staying in Cindy and Craig's rental on Fleming Street and we absolutely love it! It feels like home to us. It is clean, comfortable and close to everything. We hate to leave but always look forward to another year there.

Thank you Cindy and Craig for providing the perfect place for us to stay in Key West.

  • Submitted: Jan 5, 2014
  • Stayed: Dec 2013
  • Source: VRBO, from HomeAway
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7 1
Seattle, WA

Just perfect!

  • 5 of 5

Everything about the rental on Fleming Street was great! Craig and Cindy were friendly, quick in response times, making our reservation easy and smooth. Their information sent to us beforehand regarding recommendations on what to do while in Key West was extremely useful to us during our stay. These northwesters just loved walking into the cool air-conditioned home upon our arrival. The free wi-fi was an added plus for me as a busy professional, and allowed me to catch up with things while on vacation too. I expected a huge first grocery bill, stocking up on basics such soaps, laundry detergent, salt/pepper, paper towels, but was delighted to find all that was already taken care of for us. All the linens (including beach towels) was ready for our use, and we found the house clean, bug free and the beds comfortable to sleep in. The location was as advertised: safe and secure, close to everything and yet quiet and peaceful when we were at 'home". For the Seattle guests -- there is a Starbucks 2 blocks away but don't expect Seattle prices! We cooked in at times using Craig and Cindy's well stocked kitchen and ate out a lot too using their recommendations and adding our own places as we explored. We flew into Ft Lauderdale (much cheaper than flying into Key West or Miami) and enjoyed the ride down (do stop at the Dive Museum) and having an assigned parking space for our car. We seldom used the car, but I would recommend having one as we have found walking in the humidity for these colder climate natives, shortened our distances! We loved the white sandy beaches and also used the shared pool at the Truman Annex frequently. Our snorkeling and kayaking trips was most enjoyable including watching amazing sunsets! We left the house as we have received it and Cindy and Craig refunded our security deposit promptly. All in all, a great experience renting from Cindy and Craig!

  • Submitted: Aug 24, 2013
  • Stayed: Aug 2013
  • Source: VRBO, from HomeAway
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14 0
Long island, NY

Close to Duvall

  • 4 of 5

This was a great place to stay. It is two blocks off Duvall and in walking distance of most things you want. Parking is tight for an SUV but manageable. We had a small house keeping issue that Rick, the manager for the owners handled quickly and well. Don't miss Michael's restaurant, Daddy Bones BBQ (that one is driving distance but they do deliver) Sunset at Mallory square (5 minute walk from the house) and Hemingway House. Take aqua sox to Zachary Taylor beach, it is a little rocky. Sleeper Sofa was not too comfortable for an adult.

  • Submitted: Jul 30, 2012
  • Stayed: Jul 2012
  • Source: VRBO, from HomeAway
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6 0


Car: not necessary

Truman Annex is considered the finest location on all of Key West. As a former Navy Base and summer home of Harry Truman, it is now home to an exclusive gated community and and is adjacent to the entrance to Ft. Zach beach. Harry Truman's summer home is now a museaum known as The Little Whitehouse. Truman Annex is 2 blocks from Duval Street and all its fine restaurants, nightclubs, and museums. It is also adjacent to Mallory Square and the famous Sunset Festivals.


Rates & Availability

Truman Annex House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly Event
High Season
Jan 7 2017 - Apr 21 2017
7 night minimum stay
Shoulder Season
Apr 22 2017 - May 12 2017
7 night minimum stay
Low Season
May 13 2017 - Jun 30 2017
7 night minimum stay
4th of July Week
Jul 1 2017 - Jul 7 2017
7 night minimum stay
Low Season
Jul 8 2017 - Jul 21 2017
7 night minimum stay
Mini Lobster
Jul 22 2017 - Jul 28 2017
7 night minimum stay
Low Season
Jul 29 2017 - Aug 18 2017
7 night minimum stay
Special Rate
Aug 19 2017 - Oct 20 2017
7 night minimum stay
Fantasy Fest
Oct 21 2017 - Oct 29 2017
7 night minimum stay
Oct 30 2017 - Nov 5 2017
7 night minimum stay
Nov 6 2017 - Nov 17 2017
7 night minimum stay
Nov 18 2017 - Nov 24 2017
7 night minimum stay
Low Season
Nov 25 2017 - Dec 15 2017
7 night minimum stay
High Season
Dec 16 2017 - Dec 22 2017
7 night minimum stay
Dec 23 2017 - Dec 29 2017
7 night minimum stay
New Year's
Dec 30 2017 - Jan 5 2018
7 night minimum stay

Additional information about rental rates

Tax Rate 12.5%

OUR WEEKLY RATES INCLUDE THE CLEANING FEE & NO HIDDEN EXTRA FEES THAT OTHER OWNERS CHARGE SO THEIR RATES "LOOK" LOWER. There is a $300 security deposit that is returned on check-out per terms of your lease.

Once you send us your booking information, we hold the dates in your name & send you a lease to sign & return with 1/2 down (check, mc, or visa). Once we process your lease, we send you a receipt. We will then bill you the final amount approximately 45 days prior to check-in & then check-in package is mailed to you approximately two weeks before check-in. Until you sign your lease rates are subject to change.

If you cancel up to 60 days prior to check-in, the cancellation fee is $125. If you cancel with less than 60 days to check-in, all payments made are forfeited unless we are able to re-rent the property for the same dates and same rate to another group.

Rates for Holidays & Festivals such as Fantasy Fest may be higher. Rates generally for Sat-Sat rental only.

We do offer Last Minute Specials & selected nightly rates so contact us for more info.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
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Truman Annex House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Air Conditioning ...
  • Broadband Access
  • Clothes Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Parking Off Street ...
  • Telephone
  • Towels Provided ...
  • Washing Machine
  • Wireless Internet
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • 2 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - Bedroom 1 has an en suite full bathroom.
    Bathroom 2 - Second full bathroom is in the upstairs hallway.
    Bathroom 1 - Downstairs features a 1/2 bath.
  • 2 Bedrooms, Sleeps 6
  • Bedroom 1 - 1 queen , Queen bed with en suite full bathroom.
    Bedroom 2 - 2 twin/ single , Two twin beds or will convert to a king at your request.
    Convertible bed(s) - Queen sleeper sofa.
  • One bedroom has a Queen size Bed and the other bedroom has two Twin Beds that can be converted to a King Bed through a king mattress pad and conversion kit (upon request). Queen Sleeper Sofa in the living room.
  • CD Player
  • DVD Player
  • Music Library ...
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Video Library
  • Balcony
  • Deck / Patio
  • Outdoor Grill
  • children welcome
  • non smoking only ...
Pool / Spa:
  • Communal Pool ...
  • museums
  • restaurants
Leisure Activities:
  • beachcombing
  • boating
  • shelling
  • shopping
  • sight seeing
  • walking
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • jet skiing
  • kayaking
  • parasailing
  • rafting
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • tennis
  • water skiing
  • wind-surfing
In a secluded section of the 6-block gated community of Truman Annex quietly sits 3 of the most prestigious two story private homes with high ceilings and crown molding. We consider these homes to be our personal hideaway, complete with multiple decks and patios, privacy fencing and use of the Southard Court pool around the corner. The furnishings are DELUXE and amenities include 3 flat panel TV's, DVD, CD player full of music, and high speed internet with wi-fi. As an extra bonus bring your own I-Pod or cell phone and play your music on the stereo system through our I-Pod docking station or music tower (non Apple products can play music on the tower through the headphone jack).

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