A PLEASANT STAY

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

Vacation Rental Reviews

• A Pleasant Stay

  Stayed 8 days ending in October, 2025

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  Keith M from Myrtle Beach, SC recommends this vacation rental

  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 !!!

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• Family Gathering

  Stayed 10 days ending in May, 2025

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  Paul B from Pewaukee, WI recommends this vacation rental

  Like always outstanding.

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• EYW MARCH VISIT/2025

  Stayed 7 days ending in March, 2025

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  Jane and Sterling R from MARBLEHEAD, MA recommends this vacation rental

  GREAT PLACE, GREAT LOCATION.

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• A Pleasant Stay

  Stayed 21 days ending in February, 2025

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  Dorothy K from Chicago, IL recommends this vacation rental

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

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• Delightful week

  Stayed 7 days ending in January, 2025

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  Dan C from South Deerfield, MA recommends this vacation rental

  We had a wonderful week 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 supplies that we needed were included. Great location, close to everything....including the Green Parrot!

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• A Very Pleasant Stay

  Stayed 7 days ending in November, 2024

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  Matthew S from Columbiana, OH recommends this vacation rental

  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!

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• Great Stay

  Stayed 8 days ending in November, 2024

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  a guest from Illogan recommends this vacation rental

  Perfect location and great accommodation

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• Another fantastic stay

  Stayed 12 days ending in November, 2024

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  Julie J from Tacoma, WA recommends this vacation rental

  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.

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• Truly was a pleasant stay

  Stayed 7 days ending in October, 2024

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  Mathew G from New Port Richey, FL recommends this vacation rental

  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.

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• Cayo Hueso

  Stayed 7 days ending in June, 2024

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  Tommy D from Old Hickory, TN recommends this vacation rental

  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

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• Great Spot

  Stayed 8 days ending in June, 2024

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  Anthony P from Denver, CO recommends this vacation rental

  Great location to DUVAL St and Taylor beach State Park!

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• Family get together ❤️

  Stayed 11 days ending in April, 2024

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  Paul B from Pewaukee, WI recommends this vacation rental

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

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• Key West is Our Happy Place

  Stayed 7 days ending in January, 2024

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  Stephen H from West Harrison, IN recommends this vacation rental

  We always enjoy staying in the Truman Annex.

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• Pleasant Stay is paradise

  Stayed 12 days ending in November, 2023

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  Julie J from Tacoma, WA recommends this vacation rental

  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!!

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• This condo needs renovatin

  Stayed 12 days ending in October, 2023

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  Doug M from Palm city, FL recommends this vacation rental

  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

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• Yearly visit

  Stayed 13 days ending in April, 2023

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  Paul B from Pewaukee, WI recommends this vacation rental

  Another wonderful time. The place was again just great..clean and everything I need. Perfect location close to everything. See you next year.

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• Spring Break 2023 A Pleasant Stay

  Stayed 7 days ending in April, 2023

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  Sheri O from Henderson, KY recommends this vacation rental

  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.

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• Wonderful two weeks

  Stayed 14 days ending in March, 2023

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  Sue C from Danville, KY recommends this vacation rental

  We have rented a condo in the Shipyard community in Truman Annex from Compass Realty at least 20 times. We love the location because it is within walking distance of all the places we like to go. Compass Realty makes renting very easy. We have stayed at nearly every one bedroom condo that Compass manages over the last many years. I like some a little better than others and Pleasant Stay was fine. Only one complaint. The bedroom closet was so full of bedding, blankets, pillows, etc. and with no dresser for clothes, it was difficult to find a place to put suitcases or to unpack. Also be aware that this condo does not have a dishwasher. That said, Key West is so great, a little inconvenience is ok.

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• Maybe

  Stayed 7 days ending in February, 2023

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  Thomas H from Sorrento, FL recommends this vacation rental

  Overall it was a good stay. A loading/unloading area would be nice but I understand that is not within your control. After kicking my shoes off and walking around our new home for the week, I noticed that my feet (previously clean) were black as night. Floors were dirty and rugs (bath mat) looked as they they are never washed. Tub is very slippery ( a rubber would might help). Toilet stopped up solid on second use. The water saving minimal gallonage flush might be to blame. Luckily they had a plunger and (WOW) a bottle of Draino! Neither worked and I am a fairly handy guy. A repairman/plumber was sent in short time and situation resolved. We were a little skeptical but with minimal use and extra flushes we had no more issues. Bed was a little small and mattress slopes to the center. The couch may be the same brand as bed because it also slopes to the center. Very uncomfortable. Neck is a little sore from having to look hard right to see the TV. A/C...well I assume you know because you said don't run it below 74 degrees. That 74 felt like 76 or 78. Hard to sleep when you are sweating. With the fan on high and the 6" thick North Pole bed spread removed it was tolerable. Last, we could not find the "Outside trash receptacle" but there was only a 1/3 can of trash. Didn't have time to do the laundry. With only a 1/3 can of trash and maybe a 1/2 load of laundry I truly believe the $$$ cleaning fee would MORE than cover it. That is apparently all they do for cleaning. Sorry if I sounded harsh but we have stayed at much nicer, grander homes on the water with pool and much less rules for the same price. They weren't on Key West but just. outside. I will add the location is perfect if you are walking Key West. Thanks

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• A Pleasant Stay

  Stayed 7 days ending in January, 2023

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  Stephen H from West Harrison, IN recommends this vacation rental

  We loved our stay. Absolutely love Key West!!!

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• Great stay!!

  Stayed 9 days ending in November, 2022

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  Susan H from Sisseton, SD recommends this vacation rental

  The place was clean and we had everything we needed. We loved the sun on the deck! The area was quiet and we felt very safe. We were able to ride bikes or walk everywhere we went. It was a great stay and we hope we can get back next year!!

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• Needs updating

  Stayed 10 days ending in October, 2022

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  DAVID G from PEWAUKEE, WI does not recommend this vacation rental.

  Unit needs serious updating. The bathroom fan worked the first two days then died. The garbage disposal did not work. The bathroom faucets were both loose. Everything seems to be original. Light bulbs were missing or burnt out in lamps. Stairway carpeting needs cleaning.

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• A pleasant stay

  Stayed 8 days ending in May, 2022

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  Sara Z from Parnell, IA recommends this vacation rental

  We would stay here again.

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• Vacation, sunset cruise, fishing, hanging with friends!!

  Stayed 9 days ending in April, 2022

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  Paul B from Pewaukee, WI recommends this vacation rental

  Great time. Love the location, close to Truman Park to watch sunsets within walking distance of everything. Love the Condo very clean,love sitting on the deck having my coffee and listening to the roosters. I'll be back next year.

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• Unit Needs Updating

  Stayed 7 days ending in March, 2022

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  Diane B from Mount Carroll, IL does not recommend this vacation rental.

  The unit needs updating. It has very old kitchen cabinets that are in rough shape and the tile floor has many cracks. The outer shower curtain has visible mold at the bottom and the inner plastic curtain was ripped all across the top.

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• Paradise

  Stayed 7 days ending in February, 2022

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  a guest from Randolph, NJ recommends this vacation rental

  We enjoyed this unit. The home is nicely decorated, the kitchen is easy to use and everything we needed was available. The deck is very private and quiet. A relaxing place. A lot of thought has been put into making this comfortable for the guests. My only suggestion would be installation of grabs in the bath tub.

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• Key West Truman Annex condo

  Stayed 7 days ending in January, 2022

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  Doug M from Palm city, FL recommends this vacation rental

  We stayed the first week in January. We have stayed in several of the Truman Annex condos over the years. This one has not been updated. That didn’t really affect our stay however. Overall it was a nice unit.

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• A Pleasant Stay

  Stayed 7 days ending in January, 2022

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  a guest from Huntington, IN recommends this vacation rental

  Upper unit with an amazing deck. Close to everything we needed.

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• Key west

  Stayed 7 days ending in November, 2021

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  Howard L from Kalamazoo, MI recommends this vacation rental

  Love everthing about key west , weather , people , entertainment. Unfortunately internet didnt work first 4 days tv in living NEVER worked the whole 8 days . Thought they should have offered a little money back

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• Dirty and disrespectful

  Stayed 7 days ending in November, 2021

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  Matt W from Denver, CO does not recommend this vacation rental.

  I've stayed in these properties before, but the quality was not there this go. High touch surfaces were good, but everything else was plain gross. Towel bars, racks, shelves, etc., all had a measurable layer of dust and grime. I had to clean when I got there because it grossed me out. Also, they asked to enter my rental on the first day of my stay because they were replacing cable. Firstly, after they did that the cable didn't work the remainder of the stay, then they left a note on my thermostat with words circled and underlined saying never put the thermostat below 73 or I'll be responsible for all damages, etc. I had it at 68, it was 75 out. I realize systems can freeze up but that method of communicating was extremely rude. I had zero doors or windows open and I would expect an AC system to handle a 2 degree drop, especially if you advertise you have AC. The final straw was the quality of items. The TVs could vote and you could tell. The speakers vibrated so bad you couldn't understand anything. This was low volume. Mattress wasn't bad, sofa was decent shape. The shower curtain had mold and shower liner was ripped to shreds. I plan on not staying with them again.

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• Fantasy in Key West

  Stayed 14 days ending in November, 2021

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  David S from North Port, FL recommends this vacation rental

  Nice one Bedroom with large deck. Second Floor -Ugg

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• Vacation for 2

  Stayed 14 days ending in October, 2021

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  Melanie K from Mustang, Oklahoma recommends this vacation rental

  It was convenient to everything. Patio furniture is not as shown in photos. There are only 2 small chairs.

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• A very “Pleasant Stay”

  Stayed 8 days ending in June, 2021

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  Lloyd H from Bethlehem, PA recommends this vacation rental

  This was a great location, condo was spacious enough, clean and quiet (with the exception of the roosters). Very easy walks to anything you might want to see or do on the island. We enjoy yes it totally and would stay there again.

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• Outdoor Space a Huge Disappointment

  Stayed 7 days ending in May, 2021

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  a guest from Elk Grove Village, IL does not recommend this vacation rental.

  We've stayed at the Shipyard many, many times. This unit is clean and satisfactory, HOWEVER, the pictures of the outdoor space were completely inaccurate. All that is out on this large balcony are two upright chairs and a plant stand. Would not book this unit again. Also, we were not given our parking space number, so had to go back and forth to finally find it at the end of the street, NOT in the main lot. And someone was parked in our spot!
  

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• Uncomfortable Stay

  Stayed 14 days ending in March, 2021

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  Kathleen F from Penn Field, NY does not recommend this vacation rental.

  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.

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• Nice little stay

  Stayed 7 days ending in March, 2021

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  roger b from Indianola, IL recommends this vacation rental

  It was a nice rental, but not a NICE rental, it was just ok, we love the Truman Annex area and have stayed in numerous units over the years, this one was just ok. The bedding itself was nice but the mattress was hard as a rock. The kitchen was sufficient but could use updating. The unit was very clean and served the basic purpose of a place to sleep and relax in between our outdoor activities.

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