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

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Relax on the deck surrounded by lush palm trees and enjoy the views from the adjacent building's large windows.
Enjoy cooking in this well-lit kitchen with ample workspace and modern cabinetry.
Enjoy a comfortable stay in this well-appointed room with a balcony overlooking the surrounding area, a bed, and a bathroom with a toilet and sink.
Surrounded by lush tropical vegetation, this coastal hotel features a single-story design with a balcony on the upper floor.
Enjoy cooking in this well-equipped kitchen with a microwave, oven, and refrigerator, and dine in the adjacent dining area.

Reviews

9.8 out of 10
Exceptional

Entire condo

5 bedrooms3 bathroomsSleeps 81600 sq ft

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Pool
  • Free WiFi

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

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

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 (king, queen & queen beds) plus a loft bedroom #1 with 2 additional twin beds and another loft bedroom #2 with an additional 2 twin beds for a total of 4 twin beds. 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 one of its kind) that has a peak-a-boo view of the ocean and view of the cruise ships docking at Mallory Square. 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 Smart TV in the living room. Complete stereo system with CD player full of music. 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 generally require Saturday-Saturday rentals so if your dates are not Saturday-Saturday please email us with your dates prior to booking so that we can check our calendar to see if an exception is possible.

We have many other Key West Truman Annex vacation rental listings that can be accessed via VRBO. Let us know if you have a particular interest or property size in mind.

Property manager

Craig & Cindy Key West Rentals

Languages

English

Add dates for prices

Property amenities

Beach

  • Beach towels

Pool/Spa

  • Communal pool
  • Heated pool
  • Outdoor pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Car not required
  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Living room
  • Separate dining area

Entertainment

  • DVD player
  • Music library
  • Smart TV with cable/satellite channels
  • Stereo
  • Video library

Outdoor areas

  • Balcony
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed
  • Note from host: Smoking allowed on the balconies only.

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health/beauty spa
  • Near the marina

Things to do

  • Heated pool
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Unit size: 1,600 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome

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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is not required for transportation to and from this property

About the area

Map
Key West, FL

What's nearby

  • Fort Zachary Taylor Historic State Park - 6 min walk - 0.6 km
  • Duval Street - 8 min walk - 0.7 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Mallory Square - 11 min walk - 1.0 km
  • Southernmost Point - 16 min walk - 1.4 km

Getting around

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

Restaurants

  • ‪Margaritaville - ‬10 min walk
  • ‪Blue Heaven - ‬11 min walk
  • ‪Green Parrot Bar - ‬8 min walk
  • ‪Willie T's - ‬9 min walk
  • ‪Mangoes Restaurant & Island Cuisine - ‬9 min walk

Frequently asked questions

Does Largest Shipyard Condo in the Truman Annex - over twice the size with a loft! have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Largest Shipyard Condo in the Truman Annex - over twice the size with a loft! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Largest Shipyard Condo in the Truman Annex - over twice the size with a loft!?

Check-in begins at 4:00 PM.

What time is check-out at Largest Shipyard Condo in the Truman Annex - over twice the size with a loft!?

Check-out is at 10:00 AM.

Where is Largest Shipyard Condo in the Truman Annex - over twice the size with a loft! located?

Located in Old Town Key West, this condo building is within a 10-minute walk of USCGC Ingham Maritime Museum, Duval Street, and Fort Zachary Taylor Historic State Park. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 26 out of 31 reviews
Rating 8 - Good. 5 out of 31 reviews
Rating 6 - Okay. 0 out of 31 reviews
Rating 4 - Poor. 0 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

10/10

Cleanliness

Reviews

8/10

Overall, this was a great property and was very roomy for the six of us.
Stayed 7 nights in Aug 2024

10/10

Great location! Big and spacious.
Stayed 8 nights in Oct 2024

10/10

The property was as described on VRBO. Beautiful inside and out. Great layout inside to accommodate many people and very comfortable. Condo is close to all amenities and Duval Street. We all had a wonderful vacation.
Stayed 7 nights in Dec 2024

10/10

Fabulous location, very comfortable and perfect rental for us.
Stayed 7 nights in Oct 2022

8/10

We loved this condo! Plenty of room, close to everything! Would definitely go back!
Stayed 7 nights in Sep 2024

10/10

Great place perfect location
Stayed 7 nights in Jun 2024

10/10

Our family is big and this rental was close to our other rental as well as vlose to shopping and food. Perfect for us.
Stayed 7 nights in Jun 2024

10/10

My family very much enjoyed our stay at this home. Perfect location to everything (especially the Green Parrot). The Truman Annex is the like an oasis, just beautiful. Would highly recommend as we are planning on returning some time soon.
Stayed 7 nights in Sep 2022

10/10

This was the best place for our family to celebrate my mom's 80th birthday with a week in Key West. The condo exceeded all expectations and was very comfortable for all of us. Thank you, Craig and Cindy for providing your beautiful condo for rental!
Stayed 7 nights in Dec 2023

10/10

Great time!
Stayed 7 nights in Jul 2019

10/10

Wonderful, comfortable beautifully kept condo. Great location near everything! Family vacation where we enjoyed the many local beautiful beaches and sites, a Sunset Cruise, Dolphin Snorkel, Glass Bottom Boat Ride, and the many nearby restaurants, and dessert spots.
Stayed 7 nights in Aug 2022

10/10

Perfect location to EVERYTHING!! Didn’t need to get in the car again. Nice quiet place yet close to Duval and all attractions. Lots of privacy for everyone in our group. Would stay again and recommend to others!!!!
Stayed 14 nights in May 2021

10/10

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!
Stayed 7 nights in Dec 2017

8/10

The A/C worked very poorly, we had to request a portable unit to maintain.
Stayed 7 nights in Aug 2020

8/10

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.
Stayed 7 nights in Jun 2018

8/10

Disappointed that we really wanted condo w pool and pool was closed and no discount offered
Stayed 7 nights in Sep 2022

10/10

My husband and I went to Key West a few years ago and stayed in the Truman Annex which was a perfect location. We knew when we went back this time with a group of friends that we wanted to stay in the same complex. We found this large condo that easily fit 8 people. It was nicely decorated and clean with all the essentials needed for a week stay. It is a short walk to Duval street. We drove from home and brought our bikes. We did not even use our car the entire week. You can easily walk or bike all around the Southern part of Key West from the condo. Mrs. Cindy was staying in the condo underneath ours during the week we were there. She was very sweet and accommodating. It was very easy to get in touch with her before and during our stay. I highly recommend this listing if you are looking for a great vacation with friends or family in Key West!
Stayed 7 nights in Sep 2023

10/10

Stayed 7 nights in May 2024

10/10

Of all the properties in the Shipyard condos, this one stood out as the most spacious, sleeping at least 7. There were only 4 of us--me, my daughter, and her two teenagers--but everyone wanted their own space, and this place made it easy. It was abundantly furnished, spotlessly clean, and an easy walk to Duval Street and the Fort Zachary Taylor beach.
Stayed 7 nights in Jul 2024

10/10

This is a great place to stay for a larger family! Pool was refreshing and convenient! Owners supplied all towels and linens and 5 TVs! Great place!
Stayed 7 nights in Aug 2022

10/10

Really close to everything and nice property. Will be booking again!
Stayed 7 nights in Apr 2022

10/10

Location was within walking distance to everything. New living room furniture since posted pictures. Kitchen equipped with everything we needed. Very easy check in and out. Fun Key West decor. Would definitely stay again.
Stayed 7 nights in Jul 2021

10/10

We had such a wonderful time. The condo was very clean and in a superb location. It was such a short walk to Fort Zachary-Taylor beach, which we loved. Craig and Cindy were easy to work with and always replied to my inquiries quickly. Thank you so much for letting us stay in your beautiful home away from home!!! :)
Stayed 7 nights in Jun 2021

10/10

Wonderful stay at Truman annex shipyard 260, the place was very clean & roomy, 3 outside decks for relaxing, the pool was great! Short walk to all amenities!! Beach -bars -restaurants - shopping!! We had a fantastic time!! Plenty of room for family and friends...we were 3 couples in dire need of a getaway...we got all that and more!! Highly recommend Craig & Cindy they were easy to work with and wonderful hosts! Great experience in Key West can’t wait to go back!
Stayed 7 nights in Apr 2021

10/10

This is a great property with everything was as advertised. We had six adults in our party ranging from 24 - 50 years old. - Quiet location steps from Duval Street. Favorites Blue Heaven and Green Parrot couldn't be any closer. Recommend you tour the Coast Guard Cutter USCGC Ingham Museum just behind the property. - Gated community for added security. - Grounds and common spaces were extremely clean and overflowing with mature tropical vegetation. Really beautiful. - The pool was very clean, clear water and quiet. Mostly adults all were respectful and friendly. Lounge chairs do fill up early - Parking was convenient. The owners sometimes have access to a second parking space that we were able to use during our stay. - The condo is very nice, clean and spacious. It has 3 large bedrooms, 3 full baths and the loft with two additional beds and sitting area with tv. The furniture in the family room is newer and very comfortable. Bathrooms had cool modern finishes and huge rain showers. - Beds were very comfortable after long days on the water and Duval Street. - Each bedroom has a full closet. - Nice technology - Alexa in the family room and newer tvs in bedrooms and loft. - Three balconies - one in front and one in the rear that run the length of the condo with lots of newer comfortable outdoor furniture. The third balcony was in the loft with small view of water and good for sunsets. - My only negative/challenge was my first encounter with the guard at the gate during check in. He was having a tough day and difficult to deal with. We were there to get our parking passes. His only concern was ensuring that the one car that arrived behind us during our discussion was able to get by not getting us the parking passes. Unsuccessful in the initial discussion. Had to come back later to get the passes and even then he asked that I wrap up what we need with his supervisor at 8pm that night.
Stayed 7 nights in Mar 2021