OYSTER'S PEARL

Live steps from everything that makes Key West unforgettable. This first‑floor Shipyard condo blends comfort with island charm, offering a bright interior, tile floors, and seamless indoor‑outdoor living through double doors that open to a lush private patio. The gated Truman Annex community provides resort‑style amenities, including a sparkling pool and dedicated parking. From morning walks to the beach to evenings on Duval Street, this location puts the best of Old Town right outside your door.
Please note: This property requires a 28 night minimum stay

Vacation Rental Reviews

• nice

  Stayed 7 days ending in November, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Robert W from Cleveland, OH recommends this vacation rental

  very nice place would stay ther again
  

•  

• Fantasy Fest getaway

  Stayed 7 days ending in October, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  a guest from Cedar Key, FL does not recommend this vacation rental.

  We love Key West and aim to attend Fantasy Fest each year. This was our first time renting this condo. Overall the location is great, easy walking distance to Duval, however we found it sparsely equipped in the kitchen, the only bed filled the room, and there is no patio cover , or heavy drape so the sun heats up the living space. The shower head is fabulous!

•  

• Oyster's Pearl

  Stayed 7 days ending in June, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Mark B from WASHINGTON, MO recommends this vacation rental

  great location, safe, clean, nice pool, everything you want.
  

•  

• Wonderful complex to stay in

  Stayed 7 days ending in May, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Ray V from Conifer, CO recommends this vacation rental

  Stayed in this area for over a decade. Truman Annex is the BEST location which is why we have stayed in this community many times over the years. This unit was very comfortable, well appointed, and colorful and clean. Close to everything including the best beach in Key West right around the corner in the State Park.

•  

• Love Truman Annex Condos

  Stayed 7 days ending in May, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  a guest from Staunton, VA recommends this vacation rental

  We love staying in the Truman Annex Condos. Close to Whitehead and Duval for shopping and restaurants. Easy walk to the waterfront for excellent dining with atmosphere. Easy walk to Zachary Taylor SP to enjoy the best beach on the island. No need for a rental if your plans are to stay in Key West. Compass Realty made the checkin and checkout easy.

•  

• Oysters Pearl

  Stayed 7 days ending in April, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Kevin C from Canandaigua, NY recommends this vacation rental

  Had no real problems. Communicated with rental company via email. Good instructions on how to check in & check out. Very nice place. Small but that’s all we needed. Only minor issue was the amount of construction going on. Sidewalks closed. Looking forward to returning next year

•  

• The most perfect!

  Stayed 7 days ending in March, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Stef L from Sutton Coldfield recommends this vacation rental

  The apartment is great! Well appointed and located. The bed is comfy, the deck is sunny and everything is walkable. When you're in the apartment, you feel like you're worlds away from the busy areas, as it's so quiet. The pool is very handy too

•  

• A Pearl of a Stay

  Stayed 7 days ending in March, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Margaret C from Florence, MA recommends this vacation rental

  We had a great vacation at Oyster’Pearl. Everything was as promised. We highly recommend this unit.

•  

• Great location in Key West

  Stayed 7 days ending in March, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  a guest from Berwyn, PA recommends this vacation rental

  The condo was nice, clean and modern, with a comfortable bed. It would have been nice to have more dishes though.

•  

• LOvely area of condoa

  Stayed 7 days ending in February, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  a guest from Portsmouth, RI recommends this vacation rental

  Best area to stay with convenient access to beach and town

•  

• Oyster Bay Feb 2025

  Stayed 7 days ending in February, 2025

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  a guest from Lawrenceville, PA recommends this vacation rental

  Very nice apartment , clean. patio table needs an umbrella. Double french doors only have sheer curtains, lacks a sense of privacy as you can always look into the first floor apartment .
  The new 28 day rental will not work for me , prefer 7 day , or 14 day rental.

•  

• Gorgeous condo!

  Stayed 7 days ending in April, 2024

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Patrice L from Naples, FL recommends this vacation rental

  We loved our stay in Oyster’s Pearl! The updated kitchen was truly gorgeous! Beautiful colors! I loved the updated bathroom with a magnifying mirror in the cabinet too! Lovely unit. The Truman Annex is the best location on the island. We will definitely book this unit again!

•  

• 10's All Around!

  Stayed 7 days ending in April, 2024

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Manuel P from Palm Springs, CA recommends this vacation rental

  My husband and I just spent a week at Oyster's Pearl and LOVED every second! The rental company is super informative, close by and attentive. The property is clean, stocked with everything that we needed, super comfortable bed, had 2 bikes, beach chairs and close to all the activities that we were into. The pool is awesome and Truman Annex is safe, clean and beautiful! We can't wait to book our next trip to Key West and stay there again!

•  

• Shipyard

  Stayed 7 days ending in March, 2024

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  a guest from Danvers, MA recommends this vacation rental

  The unit was clean upon arrival. The surrounding units were quiet as were us

•  

• Nice place for a couple

  Stayed 7 days ending in February, 2024

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Frederick R from West Islip, NY recommends this vacation rental

  Very, clean, cute and great location. Needs a new couch.. Management was very very helpful. Only problem was it needs a modern (bigger) toilet bowl

•  

• Unpredictable Issues? not so fast

  Stayed 2 days ending in December, 2023

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Lawrence B from Fenton, MI does not recommend this vacation rental.

  We arrived in the rain and had to figgier out a lock box that was miss marked. after some time trying to figure out, I called and left a message explaining the situation outside in the rain. I was told the number that they had given me was incorrect and the 9 box had been switched with the 6 box (wrong name on box). This took some time, and we were finally able to get into our condo rental. The next day the ceiling started leaking water in the middle of the unit Livingroom. I called and left a message though didn't get a response for some time. By the time (this was Christmas eve) they responded the lights started flashing off and on in one of the rooms (short circuit) and my wife was afraid of a possible fire. They decided to move us to a different unit though I had to go and get keys from another lock box in the rain at 9pm. I was finally able to get the new lockbox open and we moved our things to the car and drove to the new unit. When I opened the door, the unit was full of personal items like someone was there. I slowly closed the door, and we went back to our original unit. I again called and left messages until I received a call back. They explained they were at their Christmas party and were now going to move us to a 4-bedroom unit to stay at for the remainder of our stay. The unit was very nice, and we did enjoy the remainder of our stay. What stood out for me was when they said they knew of the leaking ceiling issue and the shorting lights as the water and electricity will not cause a fire and wanted us to stay in that unit. It's definitely the Christmas eve we will remember. I realize it interrupted their Christmas party, but it was a Christmas eve event that could have been handled better.
  
  The final (last) unit was verry nice (5 stars) and I would recommend it but the first unit and second unit I would not recommend to anyone and communication getting to the last unit was a disappointment......

•  

• Beautiful Improvements

  Stayed 21 days ending in December, 2023

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Steve and Myrna H from Asheville, NC recommends this vacation rental

  We were thrilled to walk into Oyster's Pearl at Shipyard and find the kitchen and bathroom remodeled. We have stayed in this same condo for several years and always found it comfortable; however, this year was the best ever.

•  

• Perfect spot to stay in KW

  Stayed 7 days ending in November, 2023

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Sara Z from Parnell, IA recommends this vacation rental

  Wonderful location and the perfect condo for two. 5 ⭐️. Would definitely stay there again and we are repeat customers of the property management.

•  

• Very Nice Condo

  Stayed 9 days ending in July, 2023

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Bruce S from Murrells Inlet, SC recommends this vacation rental

  We loved Oyster's Pearl. Everything was as described. Perfect for a couple. We've stayed in the Shipyard many times and this condo was among the best in terms of cleaniness and complete furnishings. We'll definitely stay there again when we go back to Key West.

•  

• Disappointed in professional concern.

  Stayed 28 days ending in March, 2023

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Louise M from Berwyn, PA does not recommend this vacation rental.

  After paying $10,000 for a month's rental, I arrived to discover the kitchen is outdated, the microwave did not work, the convection oven did not work, the glass stove top was stained, the disposal is on it's last legs, the refrigerator never got cold enough and finally stopped working after only 2 weeks. Agents said how 'convenient' it was that my food could go next door in a unit for sale. Nothing was convenient for any of the above issues!
  I took cab rides to the market and had food I need to dispose. They credited me $532.00 for this inconvenience, after 5 days the refrigerator was replaced.
  For Compass to accept my $10,000, and never check the condition of the kitchen showed the complete lack of concern for their customer(s); who, pay their salary!
  
  This took the joy out of my visit to KW, and, so left one week early. I should have asked for $2,000 refund for the last week, I was exhausted with all of the continual issues and left March 17 instead of March 25.
  
  My granddaughter 31 years of age, wanted to speak on my behalf and called
  the office and spoke with Megan. Whose reply was, "None of the other tenants complained about the kitchen, your grandmother calls the office regularly. She was lucky to have her food moved next door, this isn't always the case." How unprofessional and childish and defensive. Instead of a professional response, "We are sorry your grandmother has had to deal with this 'outdated' kitchen, the kitchen should have been inspected. Which the agents should have said to me when I arrived.
  This caused great discomfort for me and took the joy out of my visit to KW.

•  

• Convenient location

  Stayed 7 days ending in January, 2023

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  a guest from Toronto, ON recommends this vacation rental

  Walking distance to everything yet quiet. Place is in good shape and has everything you need. Having a pool is a great addition.

•  

• Another Marvelous Trip to Key West!

  Stayed 16 days ending in December, 2022

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Steve and Myrna H from Asheville, NC recommends this vacation rental

  We stayed at Shipyard, Oyster's Pearl. Wonderfully comfortable place, well-equipped kitchen. Plenty of linens, etc. This is our fifth stay in the same unit.

•  

• Oysters pearl

  Stayed 7 days ending in November, 2022

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Mike U from Chesterfield, MI recommends this vacation rental

  Very clean spacious nice place

•  

• Key West Vacation

  Stayed 7 days ending in April, 2022

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  a guest from Meriden, CT recommends this vacation rental

  Perfect location.. Clean property .. Great price.. would recommend

•  

• Oyster’s Pearl Key West

  Stayed 9 days ending in January, 2022

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Maribeth H from Brant Rock, MA recommends this vacation rental

  A cute condo in the Shipyard, Key West, met our expectations. It was clean and included amenities such as a coffee maker, washer/dryer and lots of nice towels. The bedroom was small containing a queen bed. The two televisions offered basic cable so of you are interested in a wide variety of channels, you will be disappointed. The patio was pretty but offered little privacy which is expected at a condominium complex like this. The grounds were very pretty with gorgeous vegetation and tropical trees. The pool was small and crowded so we avoided going there, but with the beautiful beaches nearby, this didn’t bother us. We loved the location as it is a short walk to Duval Street and many other points of interest. All in all we would recommend this condo if you are looking for a good value and a clean place to stay.

•  

• Our Time in Oyster's Pearl

  Stayed 16 days ending in November, 2021

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Steve and Myrna H from Asheville, NC recommends this vacation rental

  We had a lovely time. This is our fourth stay in Oyster's Pearl, and we love the location, how well the condo is equipped, etc.

•  

• Great stay

  Stayed 7 days ending in November, 2021

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Paul and Barb K from Kenmore, NY recommends this vacation rental

  Condo was clean ,comfortable and located close to Duval St.
  I would stay here again & recommend to anyone looking to stay in Key West.

•  

• Oyster’s Pearl

  Stayed 9 days ending in July, 2021

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Marsha M from Greeneville , TN recommends this vacation rental

  Great accommodations. Great location. Clean. Would recommend to anyone.

•  

• unit 169 review

  Stayed 14 days ending in June, 2021

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Kathy J from Maple Shade, NJ recommends this vacation rental

  The unit was great, clean and had all supplies needed

•  

• Key West holiday

  Stayed 7 days ending in April, 2021

  • Location
    
  • Cleanliness
    
  • Services from rental manager
    
  • Overall satisfaction
    

  Property condition:

  Mike W from San Diego, CA recommends this vacation rental

  Very enjoyable stay

•