Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon
Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Largest Shipyard Condo in the Truman Annex - over twice the size with a loft!

Bedrooms 3
Space 1,600 sq ft
Property type condo
Minimum Stay 1 - 7 nights


About the property

3 bedrooms plus 2 loft bedrooms-5 different sleeping areas!! Sat-Sat preferred.

Shipyard PENTHOUSE! This unit was supposed to be 2 units but it was built as one larger unit plus two lofts were added. Three bedrooms (queen, queen & 2 twins or optional king) plus a loft bedroom with 2 additional twin beds and another loft with a queen futon sleeper. Three awesome balconies including 2 long balconies (1 covered and 1 uncovered) on the first floor and a private balcony on the loft level (only of its kind) that has a peak-a-boo view of the ocean and view of the cruise ships docking at Mallory Square. All bedrooms have a door to a balcony plus access to the balconies off the large living room and off the kitchen. Plenty of space including a large fully equipped kitchen with upgraded appliances and everything you need to cook, including essentials such as a blender for those fun drinks, coffee maker for the next day, & a microwave for the late night popcorn! Unit has a great dining room and very large living room plus 3 full bathrooms. Five flat panel TV's including in each bedroom and the loft and a large TV in the living room. Complete stereo system with CD player full of music, tower system with Bluetooth so you can play music from your phone or other device. Blu Ray DVD player with movies and much more! We even have an Amazon Echo so you can tell Alexa to play some Jimmy Buffett! Ceiling fans in every room and a great tropical feel! All linens and towels (including beach towels) are included.

Except for festivals such as Fantasy Fest, Meeting of the Minds, and Powerboat Races, we prefer Saturday-Saturday rentals.

More Details

Craig & Cindy Key West Rentals
Member since: 2001
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
September 20, 2018

About Craig & Cindy Key West Rentals

Craig & Cindy Key West Rentals have been offering vacation rentals in Key West since 1995! These are not your ordinary rentals because we also use them as our second home so have decorated them with upgraded furniture and provided everything we think you would need to enjoy your stay. We don't have to pay a commission to a third party leasing company so we can offer lower rates!

Craig & Cindy Key West Rentals purchased this condo in 2014

Why Craig & Cindy Key West Rentals chose Old Town

We have wanted this property since we started offering Key West rentals back in 1995. It is the only one of its kind and we feel it is by far the best unit in all of the Truman Annex Shipyard community. It became available about 10 years ago and we just missed out on acquiring when the prior owners talked about selling, we purchased it before it even had a chance to be listed! Yes, we LOVE this place! Since purchasing in in the Fall of 2014, Cindy has applied her 'magic' and it has been repainted, new ceiling fans, lots of new artwork, all new kitchen accessories, new linens and towels, and some new furniture. We also added flat panel TV's in each bedroom and installed a complete stereo system including a CD player full of music from Frank Sinatra to Kid Rock (with plenty of Jimmy Buffett) and a music tower that can play your music via either Bluetooth or using the headphone plug. We even have an Amazon Echo ("Alexa play some Bob Marley"). There is also a Blu Ray DVD player with movies and smart TV capacity so you can watch your Netflix.

What makes this condo unique

The ultimate flexibility in sleeping arrangements. There are 3 bedrooms (Queen, Queen & 2 Twins or optional King) plus Loft #1 has an additional 2 Twin beds and Loft #2 has a Futon queen sleeper. Thus you have 5 different sleeping areas! This unit is also by far the longest unit in the Truman Annex Shipyard community as it was originally planned to be 2 units...thus both the front and back balcony are twice as long as a normal unit. One balcony is covered and one is uncovered. Off the loft is yet another balcony and this one is as tall as the rooftops (only one of its kind) so has a peak-a-boo view of the Ocean and you can see the cruise ships docking over at Mallory Square. Of course in real estate its all about 'location location location' and you can't get any better than Truman Annex, which is at Mile Marker 0 and only 2 blocks from Duval Street and right at the entrance to Ft. Zachary Beach and next to Mallory Square and those famous nightly Sunset Festivals. While we provide an assigned parking spot, you definitely do not need a car. Save the costs of a rental car and have a great time on Duval Street! Truman Annex is a 6 block gated community that is the envy of all of Key West!


Old Town Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 2
Building Type:
  • building
  • Guests provide their own meals
Floor Area:
  • 1600 sq ft
House Rules:
  • Max. occupancy: 8
  • children welcome
  • non smoking only ...
Location Type:
  • Downtown ...
  • Ocean View ...
  • Air Conditioning ...
  • Clothes Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Telephone
  • Towels Provided ...
  • Washing Machine
  • Free Wifi
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator ...
  • Stove
  • Toaster
  • Dining ...
  • Dining Room
  • seating for 6 people
  • 3 Bathrooms
  • Bathroom 2 - toilet , shower
    Bathroom 1 - toilet , shower
    Bathroom 3 - toilet , shower
  • Three full bathrooms. Two are En Suite and one is off the living room.
  • 3 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 queen , Flat panel TV, En Suite bathroom & French doors to a balcony
    Bedroom 2 - 1 queen , Flat panel TV & French doors to uncovered balcony
    Bedroom 3 - 2 twin/ single , Two twins or king bed + Flat panel TV and door to balcony
  • All bedrooms have ceiling fans and flat panel TV's. Twin bedroom can be converted to a king bed at your choice. Let us know when signing your lease and our cleaning staff will use a king conversion kit (king mattress pad and king sheets & comforter).
  • DVD Player ...
  • Music Library ...
  • Stereo ...
  • Television ...
  • Video Library ...
  • Balcony ...
Pool / Spa:
  • Communal Pool ...
  • botanical garden
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • live theater
  • marina
  • museums
  • restaurants
Leisure Activities:
  • beachcombing
  • boating
  • eco tourism
  • paddle boating
  • photography
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • golf
  • jet skiing
  • kayaking
  • parasailing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • water skiing
  • wind-surfing
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.


4.7/5 -
(3 traveler reviews)

66% Complete
33% Complete
0% Complete
0% Complete
0% Complete
Largest Shipyard Condo in the Truman Annex - over twice the size with a loft!
average rating of 4.6666665 based on 3 reviews

Spacious condo in the heart of Old Town Key West

  • 5 of 5

We thoroughly enjoyed our stay. Coffee on the deck in the morning and cigars at night. Couldn't have asked for a better location. Quiet and peaceful but within walking distance to the best restaurants and nightlife. Rent bikes!! Best way to see and experience Key West. We rode bikes everyday to Zachary Taylor Beach. Thank you Craig and Cindy!

  • Submitted: Dec 24, 2017
  • Stayed: December 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for taking the time to write a review and we are glad you had a great time! We look forward to having you back again soon. Craig & Cindy
Did you find this review helpful?
3 0

What a fantastic vacation!!!

  • 5 of 5

Highly recommend Craig and Cindy’s Shipyard 260 Penthouse!!!

We were 6 adults and had plenty of room for a minimum of 8 people. It had everything you would need for the week, you can shop nearby for your food or eat locally at many restaraunts. It’s only a couple blocks from Duval street. We rented a few bikes from We Cycle which was 1 block away on Southard St., but there’s many places you can rent golf carts, scooters or bicycles from throughout Key West. All of which is legal to ride anywhere in Key West. Also highly recommend going to Mallory Square every night for the sunsets, street performers and vendors. You will not regret it!!!

Have fun!!!

  • Submitted: Jun 16, 2018
  • Stayed: June 2018
  • Source: HomeAway
Owner's Response: Thanks for taking the time to write a review and we really appreciate the kind words! It sounds like you had a great vacation and we look forward to having you back again soon! Key West is calling!
Did you find this review helpful?
0 0


  • 4 of 5

The property is located in an excellent location. We were within walking distance of almost anywhere we chose to go. We rented bicycles and used them everyday. The Truman Annex home association rules were very strict, I can understand why, without rules things can go south very quickly. The condo was well maintained and the grounds; as well as the pool area where beautiful. We really enjoyed ourselves. We will definitely choose a condo in the Truman annex association again.

  • Submitted: Jun 10, 2018
  • Stayed: June 2018
  • Source: HomeAway
Owner's Response: Thanks for taking the time to write a review and sorry that we did not meet your expectations that you gave us 4 out of 5 stars. Please email us as to what went wrong so we can make it right in the future.
Did you find this review helpful?
0 0


Nearest Airport
3 Miles
Key West International Airport
Nearest Barpub
Green Parrot Bar
Nearest Beach
Ft. Zachary Beach
Car: not necessary

The 6 block gated community of Truman Annex is considered the finest location to stay in all of Key West. We own several properties in the Truman Annex, from smaller units to private homes. The Shipyard Penthouse Unit 260 is the largest Shipyard unit in the Truman Annex and is actually larger than 2 units and includes high ceilings, loft space, and plenty of room. The Truman Annex Shipyard Penthouse Unit 260 is at Mile Marker 0 (the Southernmost Point on the island) and just 2 blocks from Duval Street and right at the entrance to Ft. Zachary Beach and next to Mallory Square and those famous nightly Sunset Festivals. While we do provide an assigned parking space, we recommend you skip the car as you walk everywhere...and who doesn't love walking in paradise?


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

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 generally for Saturday-Saturday rentals only. We do offer Sunday-Sunday or Monday-Monday for Fantasy Fest, Meeting of the Minds, and the Powerboat race week.

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.