See all properties
Condo

OYSTER'S PEARL at The Truman Annex in Key West

Condo with patio, 6-minute walk to Duval Street

Photo gallery for OYSTER'S PEARL at The Truman Annex in Key West

Private kitchen
Private kitchen
Private kitchen
Interior
Exterior

Reviews

9.4 out of 10
Exceptional
1 bedroom1 bathroomSleeps 263.2 sq m

Popular amenities

  • Dryer
  • Parking available
  • Washer
  • Air conditioning
  • Outdoor space
  • Free WiFi

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Mallory Square
    ‪11 min walk‬
  • Place, Southernmost Point
    ‪14 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Spaces

Deck or patio

About this property

OYSTER'S PEARL at The Truman Annex in Key West

This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard backing up to the entrance to Ft Zachary Taylor State Park, which has the nicest beach in Key West. New renovated kitchen & bathroom.
“Beginning January 2026, all properties in the Truman Annex will require a minimum of a 28 night stay”

Add dates for prices

Amenities

Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
Parking available

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Welcome to Paradise!
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
  • Pool
  • Kitchen
  • Washer
  • Dryer
10.0 out of 10, (39 reviews)
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

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

About the area

Key West

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 Smathers Beach. USCGC Ingham Maritime Museum and Mel Fisher Maritime Museum are also worth visiting.
Map
Key West, FL

What's nearby

  • Ernest Hemingway Home and Museum - 6 min walk - 0.5 km
  • Duval Street - 6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 11 min walk - 1.0 km
  • Southernmost Point - 14 min walk - 1.2 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
  • ‪Moondog Cafe & Bakery - ‬8 min walk
  • ‪Kaya Island Eats - ‬7 min walk
  • ‪Santiago's Bodega - ‬6 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 We Cycle Key West, Duval Street and Ernest Hemingway Home and Museum. Fort Zachary Taylor Historic State Park and Mallory Square 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. 44 out of 59 reviews
Rating 8 - Good. 10 out of 59 reviews
Rating 6 - Okay. 3 out of 59 reviews
Rating 4 - Poor. 1 out of 59 reviews
Rating 2 - Terrible. 1 out of 59 reviews

9.8/10

Cleanliness

10/10

Check-in

9.6/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

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

8/10 Good

Andrea S.

Liked: Check-in, location

Pretty good

It was pretty good. Could have been little cleaner with updates.
Stayed 7 nights in Jul 2025
This review comes from a trusted partner site and has not been verified.

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!

8/10 Good

Dan S.

Liked: Cleanliness, location, listing accuracy

Nice stay

Enjoyed the property and location to area activities. Place was clean. Wish I was given more complete check in instructions
Stayed 7 nights in Apr 2023

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

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

8/10 Good

Sharon G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Compass changed our unit which was disappointing, but the stay was good, unit well equipped & loved the front door opening onto Southard
Stayed 13 nights in Oct 2025

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
This review comes from a trusted partner site and has not been verified.

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.

10/10 Excellent

Barry G.

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

Great

Great place
Stayed 8 nights in Apr 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kevin C.

Oysters Pearl

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: 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

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

6/10 Okay

Larry R.

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

Looks good but!

Although the location was good and the kitchen and the bathroom were new, the living room furniture is worn and should be on the curb. The bed mattress should also be tossed! did not get a good nights sleep in the whole week we there.
Stayed 7 nights in Mar 2025

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
This review comes from a trusted partner site and has not been verified.

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.

10/10 Excellent

Margaret C.

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

Great stay

Everything was as advertised. Lovely spot. We has to leave early and received an unexpected partial refund.
Stayed 7 nights in Mar 2025

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

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

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

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

10/10 Excellent

Jason R.

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

Nice getaway

Very well maintained property and everyone was extremely nice
Stayed 10 nights in Jun 2024

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

10/10 Excellent

Joni K.

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

Wonderful Key West Vacation

Awesome!
Stayed 7 nights in Apr 2024
This review comes from a trusted partner site and has not been verified.

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!
This review comes from a trusted partner site and has not been verified.

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!

About the host

Hosted by Compass Realty Vacation Rentals & Property Management

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback

Hotels

Holiday Rentals