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A Pleasant Stay at The Truman Annex in Key West

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A heated pool - A Pleasant Stay at The Truman Annex in Key West (Key West)
Living area - A Pleasant Stay at The Truman Annex in Key West (Key West)
Exterior - A Pleasant Stay at The Truman Annex in Key West (Key West)
Outdoor dining - A Pleasant Stay at The Truman Annex in Key West (Key West)
A heated pool - A Pleasant Stay at The Truman Annex in Key West (Key West)
Tucked away in Key West's old town area, Shipyard Condominiums offer a tranquil retreat. Unwind on the spacious rear deck surrounded by lush palm trees or take a short stroll to the private pool. Central air conditioning and off-street parking provide comfort and convenience.

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

Add dates for prices

About this property

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

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

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  • Kitchen
  • Washer
  • Dryer
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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 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

About the area

Located by the sea, this condo is in Old Town Key West, a neighborhood in Key West. 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 Florida Keys Eco - Discovery Center are also worth visiting. With jet skiing, scuba diving, and snorkeling nearby, you'll find plenty of adventures in the water. Visit our Key West travel guide
View more Condo rentals in Key West
Map
Key West, FL

What's nearby

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

Frequently asked questions

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

Yes, this property has a pool. Pool types include heated pools.

Is A Pleasant Stay at The Truman Annex in Key West pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Check-out is at 10:00 AM.

Where is A Pleasant Stay 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 Mallory Square are also within 15 minutes.

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A Pleasant Stay at The Truman Annex in Key West Reviews

Reviews

Wonderful

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
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

Cleanliness

10

Location

Reviews

Verified

10/10 Excellent

David W.

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

Key West is Great

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

10/10 Excellent

Elizabeth C.

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

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
From a partner site

10/10 Excellent

tony p.

Great Spot

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 to DUVAL St and Taylor beach State Park!
Stayed 8 nights in Jun 2024
From a partner site

10/10 Excellent

Dorothy K.

A Pleasant Stay

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: Great location in walking distance to everything. Compass Realty people are friendly, helpful and will fix any issue that may come up.
Verified

10/10 Excellent

Courtney H.

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

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
From a partner site

10/10 Excellent

Mathew G.

Truly was a pleasant stay

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: It was my wife and I first time together in Key West. We got married in key west and then honeymooned there as well. Location was perfect. Short walk to anywhere.
Verified

10/10 Excellent

Dan C.

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

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
Verified

8/10 Good

Clay W.

Liked: Cleanliness, location

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
From a partner site

10/10 Excellent

Carolyn W.

Great Stay

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: Perfect location and great accommodation
Stayed 8 nights in Nov 2024
From a partner site

10/10 Excellent

Matt S.

A Very Pleasant Stay

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: First time staying at this location and in this rental. The proximity to everything was very ideal, nice walks to Southernmost and to the Harbor Walk. The Green Parrot is very close by, and became our nightcap for the evening. Rental was clean and was just enough for us. The neighborhood is quaint and quiet. The pool area was very nice as well. We will be looking at this rental on our future KW stays. Thank you!
Stayed 7 nights in Nov 2024
From a partner site

10/10 Excellent

Julie J.

Another fantastic stay

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: This unit is clean, extremely well located and had the most comfortable bed. Great for relaxing after a day enjoying everything Key West has to offer. It has a private deck, which is a great place to read and watch the weather. They installed new windows over the last year and they are wonderful. It's also the only property in key west I've stayed that has a bathtub/shower, which makes me very happy.
From a partner site

10/10 Excellent

Julie J.

Another fantastic stay

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: This unit is clean, extremely well located and had the most comfortable bed. Great for relaxing after a day enjoying everything Key West has to offer. It has a private deck, which is a great place to read and watch the weather. They installed new windows over the last year and they are wonderful. It's also the only property in key west I've stayed that has a bathtub/shower, which makes me very happy.
From a partner site

8/10 Good

Tommy D.

Cayo Hueso

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: The swimming pool closed at 6 p.m.This may be a deal breaker as we enjoy taking a swim at the end of the day
From a partner site

10/10 Excellent

Paul B.

Family get together ❤️

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: Another awesome time. Third year in a row at A PLEASANT STAY. Wonderful unit, can't wait till next year.
From a partner site

10/10 Excellent

Stephen H.

Key West is Our Happy Place

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 always enjoy staying in the Truman Annex.
From a partner site

10/10 Excellent

Julie J.

Pleasant Stay is paradise

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 Shipyard Condominiums are in the prefect location. This condo is very close to almost every attraction you will want to see. The condo itself was clean and very comfortable. The deck is a fantastic place to unwind after a day of biking around Key West. The bed provides a super comfy, high quality sleep!! I am returning next year. For a single person or couple, it is truly paradise. Sunsets are located one block down the street!! Perfection!!
From a partner site

8/10 Good

doug m.

This condo needs renovatin

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 recommend this vacation rental. Reviewer Comments: This upstairs condo is in serious need of renovation. Other than painting it doesn't look like anything has been done since it was built in the early'90s. It was clean and functional but most of the units in Truman annex have been renovated. I'd stay there again but it wouldn't be my first few choices. There was a problem with the TV but it was fixed fairly promptly by Compass the property manager
Verified

10/10 Excellent

Anthony R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay!
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Agnes B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was very clean , quiet and close to everything.
Stayed 14 nights in Dec 2025
From a partner site

10/10 Excellent

Keith M.

A Pleasant Stay

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: This is a wonderful rental to stay in. This is our second time there and my wife and I love it. So nice and convenient to everything that Key West has to offer !!!
Verified

10/10 Excellent

Brent H.

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

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
Verified

10/10 Excellent

Susan B.

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

Shipyard 1 BR

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

10/10 Excellent

Belinda P.

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

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
From a partner site

10/10 Excellent

Stephen H.

A Pleasant Stay

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. Absolutely love Key West!!!
Verified

10/10 Excellent

Ronald N.

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

Very enjoyable

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