See all properties
Entire condo

Oyster's Pearl at The Truman Annex in Key West

Condo near Duval Street in Key West

Choose dates to view prices

Photo gallery for Oyster's Pearl at The Truman Annex in Key West

TV, stereo
Pool
Interior
Exterior
Pool

Reviews

9.4 out of 10
Exceptional

Entire condo

1 bedroom1 bathroomSleeps 263 sq m

Popular amenities

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

Explore the area

View in a map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪15 min drive‬

Room options

You may also like

Ad
6 outdoor pools, free cabanas, pool umbrellas

Oceans Edge Key West Resort, Hotel & Marina

Stock Island
  • Pool
  • Pet friendly
  • Free WiFi
  • Restaurant
4.5 out of 5, Wonderful, 1,865 reviews
The price is CA $268
CA $385 total
includes taxes & fees
Jun 29 - Jun 30
Oceans Edge Key West Resort, Hotel & Marina

About the area

Key West

Heart of Key West.Within a 10-minute walk of this Old Town Key West condo, you'll find Duval Street and Ernest Hemingway Home and Museum. Also, Mallory Square is within half a mile (1 km) and Florida Keys Beaches is within 2 miles (3 km).
View more Condo rentals in Key WestOpens in a new window

What's nearby

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

Getting around

  • Key West Intl. Airport (EYW) - 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

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

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

Similar properties

Apartment (2 Bedrooms) | Interior
Beach House Condo by Avantstay Communal Pool Gated Community Great Location Month Long Stays
Old Town Key West
  • Pool
  • Kitchen
  • Washer
  • Dryer
Beach House Condo by Avantstay Communal Pool Gated Community Great Location Month Long Stays

Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Food and drink

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

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center

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

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in 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

  • No pets 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
Onsite 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 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher and a smoke detector in each accommodation.

Property is also known as

Oyster's Pearl in the Truman Annex
Oyster's Pearl @ the Truman Annex Key West
GREAT DEAL!! Oyster's Pearl @ the Truman Annex
Oyster's Pearl @ the Truman Annex Private vacation home
20% Off Summer Special Oyster's Pearl @ the Truman Annex
Oyster's Pearl @ the Truman Annex Private vacation home Key West
2698-193317

Frequently asked questions

How close is Oyster's Pearl at The Truman Annex in Key West to the airport?

This condo is 4.1 mi (19-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.

Does Oyster's Pearl at The Truman Annex in Key West have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Oyster's Pearl at The Truman Annex in Key West to the beach?

This condo is a short 14-minute walk from Florida Keys Beaches and 0.8 mi (8-min drive) from South Beach. Don't forget your sunscreen!

Does Oyster's Pearl at The Truman Annex in Key West offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Oyster's Pearl at The Truman Annex in Key West?

No, there is no casino at this condo.

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

Check-in begins at 4:00 PM.

Is there free parking at Oyster's Pearl at The Truman Annex in Key West?

Free parking is not available at this condo.

Does Oyster's Pearl at The Truman Annex in Key West have a pool?

This condo does not have a pool.

Does Oyster's Pearl at The Truman Annex in Key West have a spa?

There are no spa services available at this condo.

How close is Oyster's Pearl at The Truman Annex in Key West to downtown Key West?

This condo is 0.2 mi away from Key West.

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

Reviews

9.4

Exceptional

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

9.8/10

Cleanliness

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

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

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
Verified

10/10 Excellent

Barry G.

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

Great

Great place
Stayed 8 nights in Apr 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
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!
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
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

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
Verified

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
Verified

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
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

Joni K.

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

Wonderful Key West Vacation

Awesome!
Stayed 7 nights in Apr 2024
Verified

10/10 Excellent

Shelley H.

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

Hemingway house wedding

Perfect … location, weather, decor!
Stayed 7 nights in Mar 2024
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

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
Verified

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
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
From a partner site

8/10 Good

michelle d.

Convenient location

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: Walking distance to everything yet quiet. Place is in good shape and has everything you need. Having a pool is a great addition.
Stayed 7 nights in Jan 2023
Verified

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
From a partner site

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