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Book Online or call HomeAway Booking Assistance 888-640-7927

Craig & Cindy's Truman Annex Key West Property

Bedrooms 2
Half Baths1
Property type house
Minimum Stay 1 - 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.

We have a personal website devoted to our Truman Annex properties at (just cut and paste).

More Details

Craig & Cindy Key West Rentals
Member since: 2001
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
February 21, 2018

About Craig & Cindy Key West Rentals

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!

Craig & Cindy Key West Rentals purchased this house in 2003

Why Craig & Cindy Key West Rentals chose Old Town

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.


Old Town House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Max. occupancy: 6
  • children welcome
  • non smoking only ...
  • 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
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).


Wonderful! 4.9/5 -
(12 traveler reviews)

91% Complete
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Craig & Cindy's Truman Annex Key West Property
average rating of 4.9166665 based on 12 reviews

Wonderful vacation property

  • 5 of 5

The house was in a beautiful setting and all the rooms were comfortable and nicely decorated. The bedrooms were spacious and the beds were comfortable.The kitchen was very nice and had all the necessary appliances to make cooking and cleaning up enjoyable. It was nice having the dining room table for some meals but we mostly used the back porch because the weather was so wonderful. We really loved relaxing on the porches. The gas grill was very useful during the week.

The landscaping was well maintained and attractive. We enjoyed listening to the roosters every day and seeing the iguanas climb the trees. The pool at the Annex was very enjoyable, too.

  • Submitted: May 15, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Glad you had a great time and thank you for the kind words. We look forward to having you back again soon!
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0 0

Very clean. Responsive hosts. Excellent access to Key West.

  • 5 of 5

Due to hurricane damage at this property we were moved to 502 Porter - a slightly bigger house with a private pool. Access to the city's attractions was excellent. If a half mile walk is something you're in shape to do, then almost everything in Key West will be within walking distance from Truman Annex. I would definitely stay here again. Just be aware that if you're traveling with an infant, due to liability issues, the hosts don't supply a crib or high chair. We rented ours from the "Hip Tourist". Great stay!

  • Submitted: Oct 8, 2017
  • Stayed: September 2017
  • Source: HomeAway
Owner's Response: Thanks Jeremy - we are glad you had a great time! Just to be clear we had no hurricane damage at this property other than a bad door lock on one of our hurricane impact French doors that led to the backyard deck. Because the door is a custom hurricane rated door and would not lock and because the door installers were backed up, we moved the tenants for the week. This issue has now been rectified and guests stated checking in the following week.
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0 0

We loved our short stay!!!

  • 5 of 5

We loved the 216 Fleming St. Property. Very nice place and we liked the off-the-beaten path location. It was a quiet neighborhood.

Although we had to cut our visit short due to Hurricane IRMA, we had a great time.

I would definitely use the property again in our future Key West visits.

  • Submitted: Sep 12, 2017
  • Stayed: September 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thanks for the kind words and we are glad you had a great least until Irma chased you away! Thankfully the house (and all of our Key West properties) avoided any damage from the storm and are again open for our guests. We hope to have you back again soon!
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  • 5 of 5

Visiting The Keys was an amazing experience for my family. Our stay at 216 Flemming was a vacation within itself. The home was very clean, equipped and up to date with modern amenities. Everything as promised.

  • Submitted: Jul 20, 2017
  • Stayed: June 2017
  • Source: VRBO, from HomeAway
Owner's Response: We are glad you had a great time and thank you for the kind words. We look forward to having you back as guests again soon!
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0 0
Coppell, Tx

Clean, well equipped. Perfect location

  • 5 of 5

Really nice home. I highly reccomend

  • Submitted: Jun 3, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Glad you had a great time and hope to have you back as guests again soon!
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0 0
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: July 2016
  • Source: VRBO, from HomeAway
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2 2


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

Taxes and fees are additional

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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