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

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Shipyard 260 (the "Penthouse") is a 2nd floor double unit with a loft.
Shipyard 260 (the "Penthouse") is a 2nd floor double unit with a loft.
Shipyard 260 (the "Penthouse") is a 2nd floor double unit with a loft.
Shipyard 260 (the "Penthouse") is a 2nd floor double unit with a loft.
Shipyard 260 (the "Penthouse") is a 2nd floor double unit with a loft.

Reviews

9.8 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 8148 sq m

Popular amenities

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

Explore the area

Map
Key West, FL
  • Fort Zachary Taylor Historic State Park
    ‪7 min walk‬
  • Duval Street
    ‪8 min walk‬
  • Mallory Square
    ‪14 min walk‬
  • Key West, FL (EYW-Key West Intl.)
    ‪15 min drive‬

Rooms & beds

5 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Loft Space #1

2 Single Beds

Loft Space #2

2 Single Beds

3 bathrooms

Bathroom 1

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

Bathroom 2

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

Bathroom 3

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

Spaces

Kitchen
Balcony
Separate dining area

About this property

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

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Ocean view

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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
Smoking allowed on the balconies only.

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
On-site 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

We should mention

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

About the area

Key West

Located in Key West, this condo is in the city centre. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours.
Map
Key West, FL

What's nearby

  • Fort Zachary Taylor Historic State Park - 7 min walk - 0.6 km
  • Duval Street - 8 min walk - 0.7 km
  • Ernest Hemingway Home and Museum - 12 min walk - 1.0 km
  • Mallory Square - 14 min walk - 1.2 km
  • Southernmost Point - 19 min walk - 1.6 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 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!?

Checkout 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.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 25 out of 30 reviews
Rating 8 - Good. 5 out of 30 reviews
Rating 6 - Okay. 0 out of 30 reviews
Rating 4 - Poor. 0 out of 30 reviews
Rating 2 - Terrible. 0 out of 30 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

JAMES O.

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

Amazing Vacation

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 Excellent

Terri I.

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

Wonderful

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

8/10 Good

Kate M.

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

Shipyard condo

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

8/10 Good

Roxanne P.

Liked: Check-in, communication, location, listing accuracy

Great Place

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

10/10 Excellent

melissa m. M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in May 2024

10/10 Excellent

Reed S.

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

Just about perfect

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 Excellent

Michelle M.

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

Renter

Great place perfect location
Stayed 7 nights in Jun 2024

10/10 Excellent

Nancy B.

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

Good location

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 Excellent

Heather S., Santa Fe, New Mexico

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

The best place to experience Paradise.

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 Excellent

Katelyn B.

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

Highly recommend for a large group!

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 Excellent

Brenda P.

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

Great vacation rental for group of six friends!

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

8/10 Good

Scott L.

Liked: Cleanliness, check-in, communication, location

Keys

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

10/10 Excellent

Peter G.

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

Wonderful Stay

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 Excellent

Kathleen D.

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

Key West Fun

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 Excellent

Lisa Y.

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

Family vacation

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 Excellent

Matthew S.

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

Great Place

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

10/10 Excellent

Jessica L.

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

Perfect location-better than expected!

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 Excellent

Pamela W.

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

Fantastic week

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 Excellent

Tammy B.

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

Family getaway

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 Excellent

Brian R.

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

Truman annex shipyard

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 Excellent

Doug H.

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

Great escape to Key West with friends and family.

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

10/10 Excellent

David O.

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

FAMILY Christmas in Key West

This was my 4th time staying in Key West and I have to say this was by far the best place I've stayed. The location is perfect, just a short walk wherever you want to go. We did use the heated pool and the splash area while there, both were fun for the family. The place had plenty of room for 6 adults and a 16 month old. Everything we needed was there, just needed to stop at Public's and pick up what we wanted. I would certainly recommend this place to anyone, and will book here again in the future.

8/10 Good

Nathan F.

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

Nice place but...

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

10/10 Excellent

Laura T.

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

Family Vacaton

We rented this property for our Twin HS Graduation Trip. The property was very clean and much more beautiful than the pictures! We thoroughly enjoyed ourselves!
Stayed 7 nights in Jul 2020

10/10 Excellent

Shelly M.

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

Fun time!

Great time!
Stayed 7 nights in Jul 2019

About the host

Hosted by Craig & Cindy Key West Rentals

Host profile image
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!

Why they chose this property

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 once many years ago and we just missed out on acquiring it...so 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 the property, Cindy has applied her 'magic' and it has been repainted, new ceiling fans, lots of new artwork, completely remodeled kitchen, new linens and towels, new furniture and we added a third full bathroom and remodeled the other two full bathrooms, installed a new flooring, and revamped the loft to add 4 twin beds. We also added flat panel TV's in each bedroom, a large Smart TV in the living room, and installed a complete stereo system including a CD player full of music from Frank Sinatra to Kid Rock (with plenty of Jimmy Buffett). We even have an Amazon Echo ("Alexa play some Bob Marley"). There is also a Blu Ray DVD player with movies and Smart TV so you can watch your Netflix.

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

The ultimate flexibility in sleeping arrangements. There are 3 bedrooms (King, Queen & Queen beds) plus Loft #1 has an additional 2 Twin beds and Loft #2 also has 2 additional Twin beds. 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!

Languages:

English
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