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Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0

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Truman Annex 2nd floor Shipyard Condo with 2 balconies & great views!
Truman Annex Shipyard #265, a second floor end unit.
Truman Annex Shipyard #265, a second floor end unit.
Truman Annex Shipyard #265, a second floor end unit.
Truman Annex Shipyard #265, a second floor end unit with sleeper sofa.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms1 bathroomSleeps 4678.1 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪6 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪13 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Twin Beds

Living Room

1 Double Sofa Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Hair dryer

Spaces

Kitchen
Balcony
Dining area

About this property

Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0

Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include:

2 bedrooms 1 bath {queen and 2 twins (or we can convert the 2 twins to a king bed with a king converter) plus a sleeper sofa in the living room.

Fully equipped kitchen with upgraded appliances and cooking accessories.
Washer & dryer with iron & ironing board.
All towels and linens, including beach towels.
Central air & ceiling fans.
Second floor condo with outdoor balconies (or ask us about renting both an up and down Shipyard condo for even more room)
Large shared Shipyard pool located just steps away.
Flat Panel TV's and entertainment center.
High speed internet with Wi-Fi.
Assigned parking spot for 1 car.

Located in prestigious Truman Annex at Mile Marker 0 - location, location, location. Shipyard Condos are right at the entrance to Ft. Zachary Beach and next to Mallory Square and those famous nightly Sunset Festivals and just two blocks from Duval Street and all of the shops, restaurants, night clubs and museums. While we provide a parking spot, you will not need a car!

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.
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

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

About the neighborhood

Key West

Old Town Key West, a neighborhood in Key West, is home to this condo. 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. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting.
Map
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

  • Key West Intl. Airport (EYW) - 19 min drive

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Rams Head Southernmost - ‬7 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk

Frequently asked questions

Does Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0 have a pool?

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

How much does it cost to stay at Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0?

As of Apr 10, 2026, prices found for a 1-night stay for 2 adults at Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0 on Jun 20, 2026 start from $373, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0 pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0?

Check-in begins at 4:00 PM.

What time is check-out at Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0?

Check-out is at 10:00 AM.

Where is Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0 located?

Located in Old Town Key West, this condo building is within a 10-minute walk of Truman Waterfront Park, Duval Street, and Ernest Hemingway Home and Museum. Fort Zachary Taylor Historic State Park and Mallory Square are also within 15 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 17 out of 17 reviews
Rating 8 - Good. 0 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Gary D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a beautiful property in the perfect spot close to everything. Nice and clean no issues quiet I would go back there in a heartbeat.
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Lyndsay S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent Stay

Such a fantastic place to stay! Very clean, amenities were wonderful, and the location couldn’t have been better! Thank you to Craig and Cindy for a fabulous week in the Keys! We will definitely be back!
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Charles T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

265 shipyard

Great place. We would stay again!
Stayed 7 nights in Sep 2023
Verified

10/10 Excellent

Lori W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great week

nice condo in great location! Property manager was great to work with!
Stayed 7 nights in Oct 2019
Verified

10/10 Excellent

Beth C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The best!

We loved our stay at the Shipyard. It was absolutely wonderful and had everything we needed for a comfortable stay in Key West. We could not have asked for more!!! If you are coming to Key West I would highly recommend this condo!! Thank you!!
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

Timothy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay at Shipyard Condo

Craig and Cindy's place is one of the nicest rentals we have stayed in. It had everything we needed, was in a prime location, and was in a quiet neighborhood. It would have been perfect, if the pool had been open. (Craig and Cindy let us know well in advance that it was going to be closed for maintenance during our stay.). We would definitely stay here again!
Stayed 7 nights in Sep 2022
Verified

10/10 Excellent

Ryan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice condo in Truman Annex

Nice and clean condo. Truman Annex is a lovely neighborhood within a fifteen minute walk of everywhere you need to go in Key West. Best sunset around is at Truman Waterfront Park, right behind the complex. If you like to cook on vacation like we do, just note there is no grill on property. Kitchen is well appointed with all the basics.
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

john l.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Trip to Key West

Check in and check out was seamless. The property was exactly as described. A nice touch was they left some of the supplies (as did we) from previous guests which make the initial shopping trip much easier. The property was in great condition and very quiet, the pool was very nice and the location is great. The we had one minor problem, the property manager knew exactly what it was and we were able to resolve it ourselves in two minutes.
Stayed 7 nights in Oct 2023
Verified

10/10 Excellent

Terri M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

First time in Key West.

It's a nice gated area. It had everything we needed if we choose to eat in. They supplied us with a list of places near by from grocery stores to tours, shops and rentals to get a round with. There wasn't a dishwasher in our place but it was okay. If I go again I'll pick a place on the first floor. The second floor has a nice scenery but the stairs were a bit much for me. That's on me.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Rebecca H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet, yet close to the action.

Ease of renting and check in was amazing. Property was clean, had everything we needed. Everything worked well in the unit, except for one remote that did not have batteries. We had also asked for the two twins to be converted to a king, but that was not done - but wasn’t a big enough inconvenience to call anyone to get it rectified. It’s just under a mile to Mallory Square, a few blocks to Duval. If you go through the back of the complex, you’re right at Ft. Zachary Taylor state park. The complex was very quiet, no revelry noise or traffic noise intruded.
Stayed 7 nights in Sep 2019
Verified

10/10 Excellent

Jennifer H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location!

We had a wonderful time! Check in was very easy! Condo was beautiful and clean! 2 blocks from Duval street. Short walk to the Southern Most Point. We walked most places. We rented a golf cart for a few hours to pick up groceries and ride around and explore but since parking is such a hassle in KW, we decided to walk everywhere and we were able to do that easily with this great location!
Stayed 7 nights in Aug 2021
Verified

10/10 Excellent

Jenna S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property, perfect location

Craig & Cindy’s condo met all of our needs and was in the perfect location! Favorites about the condo: 2 balconies, walking distance from everything in the heart of Key West, the property has a pool, washer and drier in unit, two twin beds were turned perfectly into a king for us. Thank you again for a wonderful stay!
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Melissa K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful

We loved it! Everything was perfect!
Stayed 7 nights in Jun 2021
Verified

10/10 Excellent

Deb P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location and vacation

Relaxing; had issue with shower but property manager came right away and fixed the issue . Highly recommend!!
Stayed 7 nights in May 2021
Verified

10/10 Excellent

Donna P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

As Advertised!

This is a great property for 4 travelers. Clean, up-to-date, great location to most of the night life, walking distance to many things, golf cart rentals nearby if you don't have a car and tire of walking. Quiet neighborhood near Fort Zachary State Park. And the attention to detail from the owners when they send your lease packet is incredibly helpful for first time visitors. Be cautious of the stairway if you've spent a little too much time imbibing on Duval St! Bring your own hair dryer and plan on small loads of laundry vs large loads because the washer/dryer is apartment size but it was great to have it regardless. We will rent from Cindy & Craig again - no question!
Stayed 7 nights in May 2019
Verified

10/10 Excellent

Ron G.

Nice condo in great location

Property was exactly as depicted in description. Nice quiet location just a couple blocks from Duval Street. No issues whatsoever. Well run rental process and great communication by owners. I would stay here agin.
Stayed 7 nights in Dec 2018
Verified

10/10 Excellent

Danny G.

No place like home, but this place is close!!!

Our stay was wonderful, It was more than expected. Really clean, great location. All the amenities of home. I will say that parking is limited and if you want to rent a golf cart or moped and you have a car you will have to park it in the street, and that parking is very limited. We will stay here again.
Stayed 7 nights in Oct 2018

About the host

Hosted by Craig & Cindy Key West Rentals

Host profile image
Craig & Cindy Key West Rentals has been offering vacation rentals in Key West since 1995 and offer many properties from Mile Marker 0 to Mile Marker 5 that can be accessed via VRBO.

Why they chose this property

The Key West Truman Annex Shipyard Condo remains the most popular property to rent in Key West. Truman Annex is by far the best location in Key West and the Shipyard Condo is the most reasonably priced unit available. This unit is two bedrooms one bath and can sleep up to four or you can rent multiple Shipyard Condos as we have several in the same area for larger groups.

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.

What makes this property unique

Location Location Location!!! Mile Marker 0 and next to Ft. Zachary Beach, Truman Waterfront, and Mallory Square for those famous nightly Sunset Festivals. Truman Annex is a gorgeous 6 block gated community of upscale condos and homes with private security...but yet only 2 blocks from all the action on Duval Street. Location Location Location!!

Languages:

English

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