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Oyster's Pearl at The Truman Annex in Key West

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

Private kitchen
Pool
Living area
Private kitchen
Private kitchen

Reviews

9.4 out of 10, Loved by Guests
Top 10% based on
1 bedroom1 bathroomSleeps 263.2 sq m

Popular amenities

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

Explore the area

View map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪6 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪13 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 inviting first‑floor 1‑bedroom, 1‑bath property in the coveted Truman Annex offers a renovated kitchen, an updated living room seating area, and a cozy bedroom with a queen‑size bed, making it the perfect Key West retreat. Guests enjoy access to a communal pool, Wi‑Fi, and the convenience of an in‑unit washer and dryer, along with a regular drip coffee maker and all the essential appliances needed to feel right at home. Ideally located just steps from Duval Street’s dining, shops, and entertainment, it’s also only a 15‑minute walk or 10‑minute bike ride to the island’s best beach at Fort Zachary Taylor State Park. The community provides plenty of bike racks for your rental bikes—the easiest and most enjoyable way to get around Key West—and nearby grocery stores make it simple to pick up all your necessities. A private outdoor deck offers a beautiful, quiet space to enjoy your mornings or afternoons, complete with an umbrella for shade, and an off‑street designated parking space adds extra ease to your stay.
Please note: This property requires a 28 night minimum stay

Add dates for prices

Amenities

Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
Parking available

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House Rules

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

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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

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

What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Duval Street - 6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum - 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

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Willie T's - ‬6 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬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 does it cost to stay at Oyster's Pearl at The Truman Annex in Key West?

As of 28 March 2026, prices found for a 1-night stay for 2 adults at Oyster's Pearl at The Truman Annex in Key West on 23 April 2026 start from NZ$239, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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.

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. 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

10/10

Check-in

9.6/10

Communication

10/10

Location

9.8/10

Listing accuracy

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
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

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

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

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

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

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
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

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

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

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

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

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
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

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
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
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
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

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

About the host

Hosted by Compass Realty Vacation Rentals & Property Management

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