A SOUTHARD PEARL

A "Southard Pearl" is a charming condo in the Shipyard in the Truman Annex and is outfitted with washer/dryer, pots/pans, towels, linens, central air conditioning, off street parking, and heated pool access. Just inside Truman Annex's main gate on Southard Street, this is a well-appointed, one-bedroom, second floor, end unit with quiet three-side exposure to tropical views and breezes. Southard Pearl, decorated with private art and lots of mirrored walls, boasts a large rear deck with a 50% overhang to protect you from the elements while enjoying the shade of lush palm trees and other vegetation. Shipyard Condominiums are located in the prestigious gated community of the Truman Annex in Key West’s Old Town neighborhood. The condos are located 2 blocks from Duval Street and many Key West attractions. The properties are also ¼ mile walk//drive/scooter, etc. from Fort Zachary Taylor State Park and Beach. Full access to a heated community pool and assigned off street gated parking.
Please note: This property requires a 28 night minimum stay.

Vacation Rental Reviews

• Southerd Pearl

  Stayed 28 days ending in January, 2026

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  Michael O from Jasper, TN recommends this vacation rental

  Condo was exceptionally clean! Mgt company went out of their way, called us when packages arrived in their office and our coffee pot died on a Saturday morning and we had a new one by 10:30!
  
  Only issue and it’s a small one is the outside cushion have seen much better days and need replaced.
  
  Great location!

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• Best Stay In Key West

  Stayed 10 days ending in November, 2025

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  Helder C from Hamilton Parish, Hamilton recommends this vacation rental

  As soon as I opened the door and went up the stairs and saw this apartment I instantly loved it. Perfect size, layout and loved it had a balcony. Everything was clean, organized and ready for my stay. It was the perfect location as I was there to participate in the Key West world championship boat racing. I would book this apartment year after year without hesitation. Thank you to your staff for a smooth booking procedure and hassle free stay.

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• Another perfect stay

  Stayed 7 days ending in October, 2025

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  Lisa S from New Orleans, LA recommends this vacation rental

  Stayed in the condo for a week celebrating our anniversary. Love Key West

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• Great Stay!

  Stayed 14 days ending in May, 2025

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  Dawn W from New York, NY recommends this vacation rental

  Loved this unit! it was clean and well-appointed, and the location was great! Would definitely book it again!

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• Review - Southard Pearl

  Stayed 7 days ending in March, 2025

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  a guest from Washington, DC recommends this vacation rental

  Overall, the experience was excellent. The rental had all of the amenities that would make a stay ideal. Everything was spotless. I would highly recommend this location to anyone looking for a perfect vacation spot.

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• Another perfect stay

  Stayed 7 days ending in January, 2025

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  Lisa S from New Orleans, LA recommends this vacation rental

  We have stayed at many different properties in the Annex. This is tops on our list. As always, the property managers were very accommodating and helpful! Can't wait to return!!

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• Perfect Pearl on Southard

  Stayed 7 days ending in December, 2024

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  Robyn M from Rising Sun, IN recommends this vacation rental

  This is our second stay in the Shipyard and first at Southard Pearl. It lived up to all expectations - great location to Duval and everything Old Town, the condo was as pictured, the back deck was private overlooking the courtyard. Compass Realty was awesome - very responsive and answered all our questions. Would definitely book this unit again as well as work through Compass when finding a rental.

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• On A Scale of 1-10 It Was A 7

  Stayed 7 days ending in November, 2024

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  Mike S from Pensacola, FL recommends this vacation rental

  The only issues were related to the TV service and the internet service. The source of the problem was the same for both services. There were printed directions for operating the TV which were incorrect and outdated. The printed instructions for the internet were also wrong. Otherwise it was fine for two people.

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• Great condo for couples

  Stayed 7 days ending in April, 2024

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  a guest from Worcester, MA recommends this vacation rental

  Well equipped condo in a great location. Everything you want to do within walking distance. Property is well maintained and the proximity to Zachery Taylor State Park and beach a 5 minute walk. Would definitely rent again.

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• I'll be back!

  Stayed 7 days ending in November, 2020

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  Lisa O from ESSEX, MA recommends this vacation rental

  Everything about this rental was great - the location and the unit itself. The location of the Truman Annex is close to so much, but set apart enough as a residential community, so that it's quiet and peaceful. The City's waterfront park is directly behind and a great alternative to Mallory for those days you want to catch the sunset in a more low key environment. The unit at Seagull Lull was so comfortable and very clean. The rear deck was probably where I spent the most time - even though other units are nearby, the deck felt private, up among the trees - I just loved it. I can't say enough good things about the spot and the unit, and I honestly can't think of one thing wrong with the entire visit!

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• Location

  Stayed 7 days ending in October, 2020

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  Charles E from DRYDEN, MI recommends this vacation rental

  Though this unit is in need of a update everything you expect was there. We enjoyed the back deck, pool and ease of coming and going. Would we book it again? Yes. 6th time in the Annex and each unit has its pluses and minus just weigh then a pick one you’ll enjoy yourself.

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