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A Pleasant Stay at The Truman Annex in Key West

Condo near Duval Street in Key West

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Photo gallery for A Pleasant Stay at The Truman Annex in Key West

A heated pool
Living area
Exterior
Outdoor dining
A heated pool

Reviews

9.2 out of 10
Wonderful

Entire condo

1 bedroom1 bathroomSleeps 21 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

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

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About the neighborhood

Key West

Seaside stay .Within a 10-minute walk of this Old Town Key West condo, you'll find Duval Street and Ernest Hemingway Home and Museum. Also, Florida Keys Beaches is within half a mile (1 km) and Southernmost Point is within 2 miles (3 km).
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What's nearby

  • Florida Keys Eco - Discovery Center - 3 min walk - 0.2 miles
  • 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

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.

A Pleasant Stay at The Truman Annex in Key West

Just inside the Truman Annex's main gate on Southard Street, this well-appointed, very popular one-bedroom, second floor gem features tropical views and breezes and yet it's only two blocks from the heart of Old Town Key West, with an easy walk to restaurants, shops and many other Key West attractions. A Pleasant Stay boasts a large rear deck with a 50% overhang to protect you from the elements while enjoying the shade of lush palm trees and other vegetation. You'll stroll through floral-lined lanes to Shipyard's around-the-corner private pool. Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, central air conditioning, off street parking, and pool access.
Please note: This property has a 28 night minimum stay

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Property amenities

Pool/Spa

  • Communal pool
  • Heated pool
  • Private pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby

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

  • Gated community
  • Unit size: 1 square foot

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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. 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

Pleasant Stay Truman Annex House Key West

Pleasant Stay Truman Annex House

Pleasant Stay Truman Annex Key West

Pleasant Stay Truman Annex

A Pleasant Stay in the Truman Annex

A Pleasant Stay @ the Truman Annex Key West

A Pleasant Stay @ the Truman Annex Private vacation home

20% off Summer Special A Pleasant Stay @ the Truman Annex

2698-193239

Frequently asked questions

How close is A Pleasant Stay 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 A Pleasant Stay at The Truman Annex in Key West have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is A Pleasant Stay at The Truman Annex in Key West to the beach?

This condo is a short 12-minute walk from Florida Keys Beaches and 0.8 mi (8-min drive) from South Beach. Don't forget your sunscreen!

Does A Pleasant Stay at The Truman Annex in Key West offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at A Pleasant Stay at The Truman Annex in Key West?

No, there is no casino at this condo.

What time is check-in at A Pleasant Stay at The Truman Annex in Key West?

Check-in begins at 4:00 PM.

Is there free parking at A Pleasant Stay at The Truman Annex in Key West?

Free parking is not available at this condo.

Does A Pleasant Stay at The Truman Annex in Key West have a pool?

Yes, there's a private pool.

Does A Pleasant Stay at The Truman Annex in Key West have a spa?

There are no spa services available at this condo.

How close is A Pleasant Stay at The Truman Annex in Key West to downtown Key West?

This condo is 0.2 mi away from Key West.

A Pleasant Stay at The Truman Annex in Key West Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 45 out of 69 reviews
Rating 8 - Good. 17 out of 69 reviews
Rating 6 - Okay. 6 out of 69 reviews
Rating 4 - Poor. 1 out of 69 reviews
Rating 2 - Terrible. 0 out of 69 reviews

9.2/10

Cleanliness

Reviews

10/10 Excellent

Agnes B.

Liked: Cleanliness
It was very clean , quiet and close to everything.
Stayed 14 nights in Dec 2025

10/10 Excellent

Anthony R.

Liked: Cleanliness
Wonderful stay!
Stayed 7 nights in Dec 2025

10/10 Excellent

Kathy P.

Stayed 7 nights in Jul 2025

10/10 Excellent

Susan B.

Liked: Cleanliness

Shipyard 1 BR

perfect size with a great porch.
Stayed 7 nights in Apr 2025

8/10 Good

Alex S.

Stayed 14 nights in Mar 2025

8/10 Good

Ronald E.

Liked: Cleanliness
Stayed 7 nights in Mar 2025

10/10 Excellent

Dan C.

Liked: Cleanliness

Delightful week

We had a wonderful week staying in unit 102-11. Very clean, nice deck, comfortable bed and couch. Kitchen had everything we needed. Made good use of the washer and dryer. All needed supplies were in the unit. Excellent location. Close to everything….including the Green Parrot!
Stayed 7 nights in Jan 2025

8/10 Good

Clay W.

Liked: Cleanliness

Incredible Location!

The property is in an incredible location for visiting Key West. We would stay at the property again. The unit itself was dated and a bit tired. It is in need of updating and refreshing. I would not stay in the same unit again at the price. The unit also had bugs and spiders; it is south Florida so it did not freak us out but it would some people.
Stayed 10 nights in Dec 2024

10/10 Excellent

Elizabeth C.

Liked: Cleanliness

A VERY pleasant stay!

Everything was within walking distance, and being so near the Truman Water park for sunsets was fantastic! We enjoyed the small neighborhood feel of the Truman annex and are planning to return next year!
Stayed 7 nights in Jul 2024

10/10 Excellent

Ed H.

Liked: Cleanliness

WiFi

Had trouble with password taking affect.
Stayed 7 nights in Mar 2024

10/10 Excellent

David W., Williams Bay Wisconsin

Liked: Cleanliness

Key West is Great

The condo is as described with a great location.
Stayed 7 nights in Feb 2024

10/10 Excellent

Courtney H.

Liked: Cleanliness

2nd wedding anniversary

Wr enjoyed our stay very convenient to duval street. Loved the condo and will definitely want this location again in 2 yrs when we come back as we come to key west every other year since we got married in key west in 2021.
Stayed 8 nights in Jun 2023

10/10 Excellent

Belinda P.

Liked: Cleanliness

Pleasant Stay

Overall very satisfied with our accommodations. We highly recommend this Condo for it’s location and community setting. We rented bicycles for the week and it was easy to get out and explore everything Key West has to offer.
Stayed 7 nights in May 2023

10/10 Excellent

Brent H.

Liked: Cleanliness

Great little place

This condo was a great little place to stay in Key West. It was within walking distance of just about everything. We would definitely stay there again.
Stayed 7 nights in May 2023

8/10 Good

jim h.

Disliked: Cleanliness

Buffet show

Unit needs updating
Stayed 7 nights in Feb 2023

10/10 Excellent

Ronald N.

Liked: Cleanliness

Very enjoyable

Small but nice. No diswasher but lots of supplies in the unit.
Stayed 7 nights in Jan 2023

10/10 Excellent

Susan H., Lake City SD

Liked: Cleanliness

Great location and everything we needed

The place was clean and had everything we needed. We really enjoyed the morning sun on the deck. The location was very close to Duval which was great since we either walked or rode bikes. It would have been nice if the bike racks were closer. We didn’t have time to use the pool but it looked nice. We do prefer key pads as it was inconvenient to sit outside while one of us returned the keys. We would definitely stay here again.
Stayed 9 nights in Oct 2022

10/10 Excellent

Verified traveler

Liked: Cleanliness

Good time

Perfect spot for everything to do
Stayed 7 nights in Jul 2022

10/10 Excellent

Thomas P.

Liked: Cleanliness

Perfect Location

Perfect location to old town. Very quiet neighborhood. The bathroom sink and bath tub drains need some attention. We would stay here again.
Stayed 8 nights in May 2022

8/10 Good

Jeff B., Indianapolis IN

Location Location Location

We love staying at Truman Annex - it’s close to everything, including the Green Parrot and a short bike ride to Fort Zach, Duval, and the pier. While we also enjoy the pool, this was our first time visiting in May and it could be quite crowded and loud. The condo was just what we needed - plenty of dishware, washer & dryer, and patio seating. Our only wish is a small one in that we wished there was more storage space for our clothes but we totally made do.
Stayed 7 nights in May 2022

8/10 Good

Sara Z.

Liked: Cleanliness

Perfect spot in KW

Stayed several days in KW. This condo is a great location with a parking spot, pool access and walking distance to a lot of popular spots. Would rent it again.
Stayed 8 nights in May 2022

8/10 Good

Ray C., Brandon, Fl

Liked: Cleanliness

Perfect location

We enjoyed our stay here. The unit itself was well stocked and clean. Outside veranda was perfect for unwinding or...winding. it's a second floor condo but the stairs weren't too bad for a Senior with a bum knee. We did wake up to ANTS the first morning in the kitchen area. The office was closed so I sent an email advising of the problem. Never did get a response but we solved the problem with a $5.00 ant trap from CVS. Not a deal killer but that should be addressed. Location: We've stayed in KW many times and this was the best so far. The Truman Annex is just enough off the beaten path to be very peaceful in the evenings. Nice walking area close to a beautiful park just steps away to your left. Walk 1 1/2 blocks the other way(East) and you're on Whitehead St, 1 block from Duvall. Courthouse Deli(breakfast) on one corner. The Green Parrot on the other. Hemingway House is just up the street. If you need bikes, we highly recommend We Cycle which is on Southard just before Whitehead. $10.00 per day. Steve was very helpful. All in all. A great 7 days
Stayed 7 nights in Apr 2022

10/10 Excellent

Bonnie S., Fleetwood, Pennsylvania

Liked: Cleanliness

Wonderful

Our stay was wonderful.
Stayed 7 nights in Apr 2022

8/10 Good

Kimberly B.

Liked: Cleanliness

Nice time at Truman Annex

Would definitely come to Truman Annex again but, would probably stay in a different house. I was hoping it would have a more coastal feel to it. The pool was nice but very small. Also, it wasn't very clear where to take the garbage and parking. We definitely enjoyed our stay.
Stayed 7 nights in Mar 2022

10/10 Excellent

Justin R.

Liked: Cleanliness

Great location

This was a great condo for 2 people. I would recommend the location as a safe and quiet place that was walking distance to almost everything.
Stayed 7 nights in Feb 2022