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Entire condo

A PLEASANT STAY at The Truman Annex in Key West

Condo with private pool, 6-minute walk to Duval Street

Photo gallery for A PLEASANT STAY at The Truman Annex in Key West

Pool
Fridge, microwave, oven, stovetop
Outdoor dining
Exterior detail
Living area
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

  • Dryer
  • Washer
  • Pool
  • Kitchen
  • Parking available
  • Outdoor Space

Add dates for prices

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

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, have central air conditioning, off street parking, and pool access. Just inside the Truman Annex's main gate on Southard Street this well-appointed, one-bedroom, second floor features tropical views and breezes. 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.

Property amenities

Pool/Spa

  • Communal 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

  • Patio

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

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

Similar properties

Beach nearby, sun loungers, beach towels

Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

  • Pool
  • Kitchen
  • Washer
  • Dryer
10.0 out of 10, Exceptional, 173 reviews
Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

Policies

Check-in

Check-in time starts at 4:00 PM
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

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

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

About the neighborhood

Map
Key West, FL

What's nearby

  • Ernest Hemingway Home and Museum - 6 min walk - 0.4 miles
  • Duval Street - 6 min walk - 0.4 miles
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles
  • Mallory Square - 11 min walk - 0.6 miles
  • Southernmost Point - 14 min walk - 0.8 miles

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk
  • ‪Kaya Island Eats - ‬7 min walk
  • ‪Santiago's Bodega - ‬6 min walk

Frequently asked questions

Is A PLEASANT STAY at The Truman Annex in Key West pet-friendly?

No, pets are not allowed at this 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 We Cycle Key West, Duval Street, and Ernest Hemingway Home and Museum. Mallory Square and Fort Zachary Taylor Historic State Park are also within 15 minutes.

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Reviews

A PLEASANT STAY at The Truman Annex in Key West Reviews

9.2

Wonderful

9.2

Cleanliness

10

Location
Rating 10 - Excellent. 43 out of 67 reviews
Rating 8 - Good. 17 out of 67 reviews
Rating 6 - Okay. 6 out of 67 reviews
Rating 4 - Poor. 1 out of 67 reviews
Rating 2 - Terrible. 0 out of 67 reviews

Reviews

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
This review comes from a trusted partner site and has not been verified.

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

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

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
This review comes from a trusted partner site and has not been verified.

6/10 Okay

Kathleen F.

Uncomfortable Stay

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was somewhat dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: The location was great. The bed was awful,very uncomfortable. The pictures show a table and chairs on the deck , but there was only a table,no chairs.We definitely have stayed in much more updated and comfortable units in the Annex.
This review comes from a trusted partner site and has not been verified.

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.

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

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
This review comes from a trusted partner site and has not been verified.

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
This review comes from a trusted partner site and has not been verified.

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
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

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.

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
This review comes from a trusted partner site and has not been verified.

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
This review comes from a trusted partner site and has not been verified.

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.

10/10 Excellent

Ed H.

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

WiFi

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

10/10 Excellent

David W., Williams Bay Wisconsin

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
This review comes from a trusted partner site and has not been verified.

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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Julie J., Tacoma, Washington

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!!
This review comes from a trusted partner site and has not been verified.

8/10 Good

doug m., Palm City

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

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

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Paul B.

Yearly visit

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 wonderful time. The place was again just great..clean and everything I need. Perfect location close to everything. See you next year.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Paige O.

Spring Break 2023 A Pleasant Stay

Rating Details: The property manager was very helpful. The vacation rental was 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: This is the 3rd time I have dealt with Compass Realty. They are quick to respond and friendly to deal with. I have stayed at 3 properties in Shipyard Condominiums.This property was the smallest, but the location of the door on the street was a nice advantage this time. This particular property was slightly dated, but very much met our needs. There were bugs in the bathroom which would be my biggest complaint. Closet door was broken, only 5 hangers for a week stay, more would have been nice. I will continue to rent from this company as long as prices remain somewhat steady.