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.
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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 indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
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.
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
Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
Mallory Square - 11 min walk - 0.9 km
Getting around
Key West, FL (EYW-Key West Intl.) - 14 min drive
Restaurants
Green Parrot Bar - 4 min walk
Margaritaville - 7 min walk
Blue Heaven - 8 min walk
Mangoes Restaurant - 7 min walk
Rams Head Southernmost - 7 min walk
Frequently asked questions
Is A Southard Pearl at the Truman Annex in Key West pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at A Southard Pearl at the Truman Annex in Key West?
As of 5 Aug 2026, prices found for a 1-night stay for 2 adults at A Southard Pearl at the Truman Annex in Key West on 20 Aug 2026 start from AU$6,819, 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.
How much is parking at A Southard Pearl at the Truman Annex in Key West?
On-site parking is available at the property.
What time is check-in at A Southard Pearl at the Truman Annex in Key West?
Check-in begins at 4:00 PM.
What time is check-out at A Southard Pearl at the Truman Annex in Key West?
Checkout is at 10:00 AM.
Where is A Southard Pearl at the Truman Annex in Key West 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
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Rating Details:
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:
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.
A guest from Washington, DC
From a partner site
10/10 Excellent
Helder C.
15 Nov 2025
Best Stay In Key West
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:
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.
Helder C.
From a partner site
8/10 Good
Mike S.
14 Nov 2024
On A Scale of 1-10 It Was A 7
Rating Details:
The property manager was very helpful.
The vacation rental was clean.
I was more than 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 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.
Mike S.
From a partner site
10/10 Excellent
Joan D.
13 May 2024
Great condo for couples
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:
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.
Joan D.
About the host
Hosted by Compass Realty Vacation Rentals & Property Management