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Condo

Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town

Photo gallery for Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town

Exclusive gated community in the heart of OId Town Key West
Pool
Outdoor dining
Living area
Living area

Reviews

9.4 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪4 min walk‬
  • Place, Florida Keys National Marine Sanctuary
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Other Space 1

1 Double Sofa Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town

Shipyard Pool Closure
The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. We expect the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026.



Best Deal in Truman Annex – Céad Míle Fáilte!
2 Bedroom | 1 Bathroom | Sleeps Up to 5 Guests

Welcome to Innis-free, our little slice of paradise in Key West—where you're greeted with Céad Míle Fáilte, an Irish expression meaning “a hundred thousand welcomes.” Whether you're traveling from near or far, we’re delighted to share our home with you.

Nestled in the heart of the exclusive Truman Annex, our cozy ground-floor condo offers the perfect combination of comfort, convenience, and charm. With two bedrooms and one bathroom, the space comfortably accommodates up to five guests and is ideal for couples, families, or small groups of friends.

Why You'll Love It Here:
Reserved parking—leave the car and explore on foot or by bike
Steps from iconic spots: Green Parrot, Margaritaville, and Duval Street
A short ride to Fort Zachary Taylor State Park—home to the island’s best beach
Relax in the community pool or unwind on your private back deck
Enjoy tasteful decor, hardwood floors, and a new maplewood kitchen

From lazy beach days to lively nights out, everything Key West has to offer is right at your doorstep. So kick back, soak up the sunshine, and enjoy a truly warm welcome—a hundred thousand times over.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space

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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
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

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 Mel Fisher Maritime Museum are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.
Map
Key West, FL

What's nearby

  • Duval Street - 4 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 6 min walk - 0.6 km
  • Ernest Hemingway Home and Museum - 8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 9 min walk - 0.8 km
  • Mallory Square - 12 min walk - 1.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 9 min drive

Restaurants

  • ‪Green Parrot Bar - ‬5 min walk
  • ‪Margaritaville - ‬8 min walk
  • ‪Mangoes Restaurant - ‬8 min walk
  • ‪Blue Heaven - ‬9 min walk
  • ‪Rams Head Southernmost - ‬8 min walk

Frequently asked questions

Does Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town have a pool?

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

How much does it cost to stay at Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town?

As of 24 April 2026, prices found for a 1-night stay for 2 adults at Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town on 31 May 2026 start from NZ$229, 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 Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town pet-friendly?

No, pets are not allowed at this property.

How much is parking at Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town?

On-site parking is available at the property.

What time is check-in at Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town?

Check-in begins at 4:00 PM.

What time is check-out at Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town?

Checkout is at 10:00 AM.

Where is Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town located?

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

Reviews

9.4

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. 61 out of 81 reviews
Rating 8 - Good. 15 out of 81 reviews
Rating 6 - Okay. 4 out of 81 reviews
Rating 4 - Poor. 1 out of 81 reviews
Rating 2 - Terrible. 0 out of 81 reviews

9.8/10

Cleanliness

10/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

9.4/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Monika K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Closeness to everything we wanted to do.
Stayed 7 nights in Dec 2025
Response from VrboOwner on 14 January 2026
So glad that you had a fabulous stay.
Verified

10/10 Excellent

Denise R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Easy check in. Fabulous location.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 15 November 2025
Wonderful to hear. Thanks so much Denise
Verified

10/10 Excellent

Richard G.

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

Key West getaway!

Amazing quiet secluded spacious condo! Would absolutely stay here again.
Stayed 7 nights in Nov 2023
Verified

10/10 Excellent

Chris B.

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

Great place

Great location. Just positive all around
Stayed 6 nights in Jul 2023
Response from VrboOwner on 31 August 2023
Thank you Chris. You were a great guest and would most definitely be welcome back.
Verified

10/10 Excellent

Valerie D.

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

Boat Race Week

Great service by the office, great location for boat race week and general island visiting.
Stayed 7 nights in Nov 2024
From a partner site

10/10 Excellent

Paul G.

Irish Cottage in The Shipyard

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This place is very clean and well kept. Close to everything.
Verified

10/10 Excellent

Nick T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great to work with, helped immediately when an issue popped up late in the evening that was out of everyone’s control. Went out of their way to make sure we were taken care of. Thank you!
Stayed 6 nights in Aug 2025
Response from VrboOwner on 9 September 2025
Thank you Nick. This is fantastic to hear. Also we really appreciate you being understanding guests.
Verified

8/10 Good

Siniša P.

Liked: Cleanliness, communication, location, listing accuracy

Nice, close to everything

Clean and neat. Close to Duvall, yet peaceful.
Stayed 9 nights in Jul 2019
Response from VrboOwner on 21 June 2023
Thank you Sinisa, We hope you will stay again
Verified

10/10 Excellent

Valerie H.

Key West

Wonderful
Stayed 9 nights in May 2019
Response from VrboOwner on 21 June 2023
Thank you Valerie, I hope you will stay with us again.
Verified

10/10 Excellent

Louise V.

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

Overall stay was wonderful!

We enjoyed the condo and location to restaurants, Mallory square, shopping, and beaches. Things to improve: WiFi was not showing as secure dishwashing leaked on floor when ran (alerted rental Co.) keys left on table opened the pool gate but not gates to Truman annex after 6pm.
Stayed 7 nights in Apr 2024
Archival

10/10 Excellent

Sue M.

Key West Vacation

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Loved the condo, patio and location.
Response from VrboOwner on 21 June 2023
So glad you had a great time. Please come back and stay with us again.
Verified

10/10 Excellent

Shelby G.

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

Honeymoon trip

The trip was great all around. The condo was very clean & communication was easy. No problems here!!
Stayed 7 nights in Aug 2023
Response from VrboOwner on 4 September 2023
Thank you Shelby. We are glad you enjoyed your Honeymoon in Key West.
From a partner site

10/10 Excellent

Bill M.

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

Location, location, location?

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Shipyard condos are the perfect location for a Key West vacation.
Stayed 14 nights in Oct 2019
Response from VrboOwner on 21 June 2023
Thank you William, Come stay with us again
From a partner site

8/10 Good

Valerie H.

Comfortable Condo

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Condo was well equipped and very clean
Stayed 9 nights in May 2019
Response from VrboOwner on 21 June 2023
Thank you Valerie
From a partner site

10/10 Excellent

Paul G.

Irish Cottage in The Shipyard

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great spot in Key West! Near everything.
Response from VrboOwner on 21 June 2023
Best winter guests ever.
From a partner site

10/10 Excellent

Rosie B.

Beautiful location, safe gated development

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great place to stay with all amenities included, good location, walking distance to shops and museums and the beach. Very comfortable for 4 people.
Response from VrboOwner on 4 September 2023
Thank you Rosie
From a partner site

10/10 Excellent

Linda H.

Irish in Truman Annex

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Quite delightful. Great location, very clean and comfortable. However small bathroom and kitchen. Would stay there again. Julia was fabulous
Response from VrboOwner on 28 October 2023
Thank you LInda
From a partner site

10/10 Excellent

Keri A.

Perfect Location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Fantastic vacation spot. Easy access to everything. I recommend renting bikes for easy access to the beach. The house was very clean and well stocked. We greatly appreciated the beach chairs.
Stayed 6 nights in Jun 2023
Response from VrboOwner on 21 June 2023
Great to hear. Thank you
From a partner site

8/10 Good

kathryn w.

Perfect location and quiet

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Some appliances were a bit outdated but they worked. Comfortable and clean. Didn't have to buy anything extra for cleaning, paper goods, or laundry. Would stay again.
Stayed 6 nights in Aug 2023
Response from VrboOwner on 5 September 2023
Thank you
Verified

10/10 Excellent

David P.

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

Great place close to Duval

Overall a great place to stay. I would get the shower drain cover fixed. There are no screws holding it down. Also the WiFi account isn’t being broadcast. I do like it a bit cooler at night 74 was a bit warm for sleeping. Still a great place to stay.
Stayed 10 nights in Jul 2023
Response from VrboOwner on 18 July 2023
Thank you for taking the time to share your feedback. I will be certain to share the shortcomings you had mentioned to the maintenance team. Glad to hear you enjoyed your stay with us. Thanks again.
From a partner site

8/10 Good

Littleton K.

A Wonderful Time Was Had by All

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property is pretty and was clean. A bit dated inside, but a nice common space. Location was pretty great. Management company was AWESOME! Response times to needs was only a few minutes. Could use a few more kitchen items, i.e., cookie sheet, utensils.
Stayed 5 nights in Apr 2020
Response from VrboOwner on 21 June 2023
Thanks for your review. We will check on your suggestions, we appreciate the communication.
From a partner site

10/10 Excellent

Nancy and Larry M.

Truman Shipyard

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Condo was clean and in a great location for walking to many restaurants and shops in Key West. Overall the rooms are small, kitchen is one person at a time. Outdoor deck area was nice, but when we were there it was very hot outdoors, even at night, so didn't get to enjoy it much. The pool is great, had shade when needed and a short walk from the condo.
Response from VrboOwner on 11 October 2023
Thanks for your review.
Verified

10/10 Excellent

Bill M.

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

Location, location, location!

Excellent location. Unit is a bit run down and in need of updating. That said, the price was less than I normally pay for a 1 BR also in Shipyard. On arrival, the security require the name of the owner. There is no name on the contract, just the property manager. Fortunately the security guy let it slide, in the past they have more insistent. If this unit were cleaned up and the bulky furniture swapped out it would easily be a 5*.
Stayed 14 nights in Oct 2019
Response from VrboOwner on 21 June 2023
Thanks for your review. We will pass on your comments to the Owners. However you did manage to book at the low season price and it is normally not that low.
Verified

8/10 Good

Debbie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We stayed here for a week and overall the location was excellent—close to everything—and the condo itself was cozy and clean. We’ve stayed at other rentals in the Shipyard community, but this was the first that really didn’t provide any “extras.” The toilet paper was 1-ply, there were no paper plates or cups, only a half-roll of paper towels, and the complimentary toiletries were minimal (a tiny hand soap and small sample-size shampoo/conditioner).Since we travel often and usually stay for at least a week, we know to pack most of our own supplies, but it still felt a little bare compared to other places we’ve stayed. We were also asked to start the linens in the washer and dryer before leaving, but only one laundry tablet was provided. For the price we paid, it would have been nice to have at least a little more consideration—something as simple as filling the ice trays with water would’ve made a difference.That said, the condo itself was comfortable and in a great spot, just be prepared to bring along the basics if you book here.
Stayed 7 nights in Aug 2025
From a partner site

6/10 Okay

Thomas K.

OK but needs TLC

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The property was under renovation and needs some TLC - especially the back deck: door shutters were propped up against the fence along with an old bucket and a can of stain or paint. Bikes were half covered with an old, tattered blue tarp, the umbrella, door mat and cushions were worn and really need to be updated. The kitchen appliances and utensils were functional but bare minimum quality. We've stayed at many condos in Truman Annex and they were all better maintained and updated. We were also disappointed in the condition of the pool surface. I understand it will be resurfaced soon, which is good, it needs it. Overall, this property might be OK for young people there to party but middle-aged couples will probably prefer something more updated.
Stayed 8 nights in Oct 2024

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