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Oyster's Pearl at The Truman Annex in Key West

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TV, stereo - Oyster's Pearl at The Truman Annex in Key West (Key West)
Fridge, microwave, oven, stovetop - Oyster's Pearl at The Truman Annex in Key West (Key West)
Interior - Oyster's Pearl at The Truman Annex in Key West (Key West)
A water park with a red slide, a water fountain, and palm trees. - Oyster's Pearl at The Truman Annex in Key West (Key West)
TV, stereo - Oyster's Pearl at The Truman Annex in Key West (Key West)
Nestled in the back of the Shipyard, this condo offers a serene retreat with an extra large living room featuring a big screen TV. Enjoy music from your favorite services via Sonos WiFi speaker and take advantage of nearby Ft Zachary Taylor State Park with its pristine beach.

Reviews

9.4 out of 10
Exceptional

Entire condo

1 bedroom1 bathroomSleeps 263 sq m

Popular amenities

  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space
  • Parking available

Add dates for prices

About this property

Oyster's Pearl at The Truman Annex in Key West

  • 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

Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the condo: Free WiFi

Parking and transport

  • Parking on site

Food and drink

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub
  • Shower
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Stereo
  • TV

Outdoor areas

  • Fenced yard
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre

Things to do

  • Water park

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Unit size: 680 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in and check-out are available

Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

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 indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

Located in Key West, this condo is in the city centre. Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park 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. Visit our Key West travel guide
View more Condo rentals in Key West
Map
Key West, FL

What's nearby

  • Florida Keys Eco - Discovery Center
    Florida Keys Eco - Discovery Center
    3 min walk - 0.3 km
  • Duval Street
    Duval Street
    6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum
    Ernest Hemingway Home and Museum
    8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park
    Fort Zachary Taylor Historic State Park
    8 min walk - 0.7 km
  • Florida Keys National Marine Sanctuary
    5 min walk - 0.4 km

Getting around

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

Restaurants

  • Green Parrot Bar
    4 min walk
  • Blue Heaven
    8 min walk
  • Mangoes Restaurant
    7 min walk
  • Moondog Cafe & Bakery
    8 min walk
  • Rams Head Southernmost
    7 min walk

Frequently asked questions

Is Oyster's Pearl at The Truman Annex in Key West pet-friendly?

No, pets are not allowed at this property.

How much is parking at Oyster's Pearl at The Truman Annex in Key West?

On-site parking is available at the property.

What time is check-in at Oyster's Pearl at The Truman Annex in Key West?

Check-in begins at 4:00 PM.

What time is check-out at Oyster's Pearl at The Truman Annex in Key West?

Checkout is at 10:00 AM.

Where is Oyster's 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 Ernest Hemingway Home and Museum. Florida Keys Beaches and Fort Zachary Taylor Historic State Park are also within 15 minutes.

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Oyster's Pearl at The Truman Annex in Key West Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 46 out of 61 reviews
Rating 8 - Good. 10 out of 61 reviews
Rating 6 - Okay. 3 out of 61 reviews
Rating 4 - Poor. 1 out of 61 reviews
Rating 2 - Terrible. 1 out of 61 reviews

9.8

Cleanliness

9.8

Location

Reviews

Verified

10/10 Excellent

Mitch B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and property
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Jody H.

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

Lobster Season Vacation

Property was very nice and clean and well located to all Key West has to offer. Safe off street assigned parking is a huge luxury in key west!
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

April P.

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

Loving Key West

We enjoyed staying at the Southard Pearl in Key West Truman Annex. We stay stay in Truman Annex every year during the October Trop Rock event. Great music and great fun.
Stayed 7 nights in Oct 2024
Verified

10/10 Excellent

Stef L.

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

Really perfect!

The apartment is very well appointed and spacious. The bed is comfy, the kitchen well stocked for cooking, and everything is really close.Lovely to be able to take a walk to see the ocean, just minutes away, or pop up to Duval, which is just 5 minutes away.The deck and pool are very sunny too
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Renay G.

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

Excellent!

Lovely community. Very clean, close to everything. Highly recommend!! Thank you for everything. :)
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Bradley K.

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

Excellent all the way around

The owner was great to work with from reservation to checkout. The location of the unit is perfect for a stay in Key West, easy walk or Duval Loop bus to all locations. The complex is tropical and well maintained, we loved sitting on the porch watching the activities below us. Pool less than a minute walk. Short 1/2 mile walk to the state park beach with new sand. Hopefully after Jan 1st they can still rent weekly. Thanks Pam for a great stay!
Stayed 7 nights in May 2025
From a partner site

10/10 Excellent

Nancy R.

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

10/10 Excellent

John E.

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

Post Cruise

The property was quiet and well maintained. The stay was truncated due to maintenance on adjoining properties. For a 1-bedroom property it has plenty of space, and great appliances.
Stayed 6 nights in Sep 2024
Verified

10/10 Excellent

Lance D.

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

Return to Key West

Our last Key West vacation was 2007. When I priced out week stay at same hotel the prices were insane so checked out VRBO and found the perfect accommodation. The condo provided the privacy we prefer, and the unit fit our style perfectly. We rented a golf cart for the whole week and covered every inch of key west . We even took several trips over to Stock Island for Kayak tour. We especially liked the community swimming pool and the property management staff.
Stayed 7 nights in May 2024
Verified

10/10 Excellent

Taylor M.

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

Perfect week in Truman annex

This 1 bedroom gem in the best location on the island did everything we needed. It even had free bikes included! Beautiful kitchen. Clean and had a strong AC unit. Nicely done bathroom. The only small nit picks I could maybe say is that the tv’s are older and don’t have smart TV capability. And the bed could’ve been a bit softer. But we had a fantastic time. No real complaints here! The closet was stocked with beach chairs, bike chains, extra sun tan lotion. Would absolutely re rent here!
Stayed 7 nights in Apr 2024
Verified

8/10 Good

Jennifer W.

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

Lovely well equipped condo

The most convenient place to stay to take advantage of beach and town. It’s a beautiful and quiet area of condos. Just a couple of suggestions: 1. The listing said that we would have bikes which we did, but without baskets on them they were worthless for a ride to the beach. If we had backpacks we could have managed, but we did not. Also there were no locks for the bikes. We did not want to have them stolen and be held accountable 2. The front porch had a very bright light which we could not turn off. It shone directly into the bedroom window. The blinds on the window did little to keep out the light. Fortunately there was a curtain rod above the window and we hung a blanket from it. 3. The back deck was mostly I useable during daylight hours. There was no table umbrella to block direct sun
Stayed 7 nights in Feb 2025
From a partner site

6/10 Okay

Lawrence B.

Unpredictable Issues? not so fast

Rating Details: The property manager was adequately helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: 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......
Stayed 2 nights in Dec 2023
From a partner site

10/10 Excellent

Patrice L.

Gorgeous condo!

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: 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!
From a partner site

10/10 Excellent

clare t.

10's All Around!

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: 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!
From a partner site

10/10 Excellent

james l.

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: The unit was clean upon arrival. The surrounding units were quiet as were us
From a partner site

10/10 Excellent

Fred R.

Nice place for a couple

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: 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
From a partner site

10/10 Excellent

Myrna H.

Beautiful Improvements

Rating Details: The property manager was adequately 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: 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.
From a partner site

10/10 Excellent

Sara Z.

Perfect spot to stay in KW

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

10/10 Excellent

Randy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was very clean. Location was awesome by the pool and short walk to Duval St. Kitchen was well stocked. Nice Tv's.Back patio was nice. I would have liked a table and chairs on the patio though. Would definitely stay here again Great property.
Stayed 9 nights in Nov 2025
Verified

10/10 Excellent

Anthony D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My wife and i stayed here for a week and it was great. The check-in process was seamless. The location was perfect. Newer appliances and bathroom was everything we could ask for. We will definitely stay here again.
Stayed 7 nights in Sep 2025
Verified

10/10 Excellent

Christi R.

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

Key West Paradise

My husband and I spent a little over a week here exploring Key West. We loved the pool and the closeness to everything. The grounds were beautiful and we made friends with the lizards.
Stayed 8 nights in Jun 2025
Verified

10/10 Excellent

Barry G.

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

Great

Great place
Stayed 8 nights in Apr 2025
From a partner site

6/10 Okay

Debi A.

Fantasy Fest getaway

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: 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!
From a partner site

10/10 Excellent

Mark B.

Oyster's Pearl

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

10/10 Excellent

S

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

Felt like home!

Highly recommend, we absolutely loved stay!
Stayed 7 nights in Mar 2024