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Oyster's Pearl at The Truman Annex in Key West

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TV, stereo
TV, stereo
Pool
Fridge, microwave, oven, stovetop
Interior

Reviews

9.4 out of 10
Exceptional

Entire condo

1 bedroom1 bathroomSleeps 2680 sq ft

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.)
    ‪13 min drive‬

Room options

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About the neighborhood

Key West

Located in Key West (Old Town Key West), this condo is within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. .This condo is 0.7 mi (1.1 km) from Florida Keys Beaches and 0.6 mi (0.9 km) from Fort Zachary Taylor Historic State Park.
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What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.3 miles
  • Duval Street - 6 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 8 min walk - 0.4 miles
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles
  • Mallory Square - 14 min walk - 0.8 miles

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Rams Head Southernmost - ‬7 min walk
  • ‪Moondog Cafe & Bakery - ‬8 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
Make yourself comfortable in your air-conditioned condo, featuring a refrigerator and a microwave. There's a private patio. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub.
This smoke-free condo offers a stereo.
Guests will find features like wireless internet access and onsite parking.

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

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

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
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

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

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

10/10 Excellent

Mitch B.

Liked: Cleanliness
Great location and property
Stayed 7 nights in Nov 2025

10/10 Excellent

Randy L.

Liked: Cleanliness
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

8/10 Good

Sharon G., Longmont

Liked: Cleanliness
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
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

8/10 Good

Andrea S.

Pretty good

It was pretty good. Could have been little cleaner with updates.
Stayed 7 nights in Jul 2025

10/10 Excellent

Christi R.

Liked: Cleanliness

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

10/10 Excellent

Bradley K., Staunton

Liked: Cleanliness

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

Barry G.

Liked: Cleanliness

Great

Great place
Stayed 8 nights in Apr 2025

10/10 Excellent

Renay G.

Liked: Cleanliness

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., Freeport

Liked: Cleanliness

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., Sutton Coldfield

Liked: Cleanliness

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

10/10 Excellent

Margaret C.

Liked: Cleanliness

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

10/10 Excellent

Verified traveler

Liked: Cleanliness
Stayed 7 nights in Jan 2025

8/10 Good

Jennifer W.

Liked: Cleanliness

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

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

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

Bob C.

Liked: Cleanliness
Stayed 7 nights in Aug 2024

10/10 Excellent

Jody H.

Liked: Cleanliness

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

Nice getaway

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

10/10 Excellent

Lance D.

Liked: Cleanliness

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

Wonderful Key West Vacation

Awesome!
Stayed 7 nights in Apr 2024

10/10 Excellent

Taylor M., United States

Liked: Cleanliness

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

10/10 Excellent

Shelley H.

Liked: Cleanliness

Hemingway house wedding

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

10/10 Excellent

S

Liked: Cleanliness

Felt like home!

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

10/10 Excellent

Greg B.

Liked: Cleanliness

Oyster's Pearl was a hit.

We rented this property for one week for a trip to Key West. We go to the Florida Keys approx every year. This year we decided to use VRBO, and rented this one BR, one BA property. It was perfect for us. Close to the hustle bustle of Key West, Duval Street, Old town, etc, but just far enough away(~ 3 blocks) to be secluded and quiet. Pool was great. Property was lush with tropical foilage. This is a residential area with some part time and permanent residents. Only negative was lack of a dishwasher, but not a deal breaker.
Stayed 7 nights in May 2023