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Sailor's Story at The Truman Annex in Key West

Photo gallery for Sailor's Story at The Truman Annex in Key West

Living area
Pool
Exterior
Private kitchen
Private kitchen

Reviews

9.2 out of 10
Wonderful
2 bedrooms2+ bathroomsSleeps 61 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Air conditioning

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Twin Beds

Other Space 1

1 Double Sofa Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet

Bathroom 3

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area

About this property

Sailor's Story at The Truman Annex in Key West

The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located less than a half mile from one of the best beaches on the island, Fort Zachary Taylor State Park and Beach. The Presidents Walk properties are two level townhouses which have private courtyards on the first level and balconies on the second level. All properties are outfitted with washer/dryer, fully equipped kitchen, towels and linens, have central air conditioning, off street parking and pool access.

Please note: This property is monthly rental - This property has a 28 night minimum stay
Our prices include all fees. No hidden fees.

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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
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

About the neighborhood

Key West

Located near the beach, this vacation home 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 Mel Fisher Maritime Museum are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
View more Vacation Homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Duval Street - 5 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Ernest Hemingway Home and Museum - 7 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 9 min walk - 0.8 km

Getting around

  • Key West Intl. Airport (EYW) - 14 min drive

Restaurants

  • ‪Green Parrot Bar - ‬3 min walk
  • ‪Margaritaville - ‬5 min walk
  • ‪Willie T's - ‬5 min walk
  • ‪Blue Heaven - ‬7 min walk
  • ‪Jack Flats - ‬6 min walk

Frequently asked questions

Does Sailor's Story at The Truman Annex in Key West have a pool?

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

How much does it cost to stay at Sailor's Story at The Truman Annex in Key West?

As of Mar 31, 2026, prices found for a 1-night stay for 2 adults at Sailor's Story at The Truman Annex in Key West on Apr 26, 2026 start from $296, 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.

Is Sailor's Story 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 Sailor's Story at The Truman Annex in Key West?

Check-in begins at 4:00 PM.

What time is check-out at Sailor's Story at The Truman Annex in Key West?

Check-out is at 10:00 AM.

Where is Sailor's Story at The Truman Annex in Key West located?

Located in Old Town Key West, this vacation home is within a 5-minute walk of We Cycle Key West and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 36 out of 51 reviews
Rating 8 - Good. 7 out of 51 reviews
Rating 6 - Okay. 7 out of 51 reviews
Rating 4 - Poor. 1 out of 51 reviews
Rating 2 - Terrible. 0 out of 51 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

8/10 Good

D D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved the backyard patio. With iguana.
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Kimberly R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Overall we had a great stay at Sailor's Story in The truman Annex. She house was very clean, had everything we needed, exactly like the pictures posted, and in a great location. Would definitely stay there again.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Tisha C.

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

Overall Great Stay

The check in procress was easy, the unit was clean and good location. This our second time staying at the Truman Annex and would definitely stay again.
Stayed 7 nights in May 2023
From a partner site

10/10 Excellent

Mandy H.

Vacation in 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: Home was very clean with a tropical patio. Very close to the pool and attractions. Loved it!!
Verified

10/10 Excellent

Jayson H.

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

Key West Perfection

Everything that you would want out of a Key West visit is all here. Close to everything, great surroundings and wonderful people to work with.
Stayed 7 nights in May 2024
Verified

10/10 Excellent

Bart R.

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

Family KW trip

Excellent place to stay Excellent location Excellent communication I do think the decor could be updated Definitely would stay there again
Stayed 7 nights in Nov 2024
Verified

10/10 Excellent

Donna S.

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

Key West Vacation April 2024

The Sailor's Story was very clean. It was close to everything that we wanted to go to on Duval St., Hemingway House. Michelle from Compass Realty was very helpful with any questions we had, Will stay there again .
Stayed 7 nights in Apr 2024
From a partner site

10/10 Excellent

chris h.

Great Location

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: Condo was very clean, well appointed, and the location was great.
Stayed 7 nights in Nov 2023
Verified

10/10 Excellent

Katie C.

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

Beautiful neighborhood

Great place to stay. Helpful staff. The neighborhood is so picturesque. Pool is nice. Parking is very very tight. And figuring out how to get in and out of the Annex is challenging but once you figure it out, it’s easy!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Joe M.

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

Great location

We have stayed in Truman Amex many times. and enjoyed our stay. The property was well appointed with close proximity to the pool and parking. Electronics all easy to use with fast internet. The only improvement would be the inclusion of some beach chairs
Stayed 7 nights in Feb 2023
From a partner site

10/10 Excellent

John S.

Birthday Celebration

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 with pool to relax during afternoons
From a partner site

10/10 Excellent

Kim S.

Great place for a great vacay

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 the second time we have stayed in this place. It is perfect for our trip. Close to everything we want to do. Great pool. The place is clean and comfortable. We will be staying there again for sure.
From a partner site

10/10 Excellent

julie d.

A Tremendous Week!

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: Sailor's Story was the perfect getaway from the frigid cold of Wisconsin. The accommodations, pool, and staff made for a great vacation.We will be back!
From a partner site

10/10 Excellent

Very nice place to 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: It is a nice, well equiped apartment with a lovely king size bed. For us the steep staircase was a little problem but we are 70+. The railing could be improved (only one side now).The first rental car (a big SUV) didn't fit in the assigned parking.
From a partner site

10/10 Excellent

Scott M.

Great location, great space!

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: Highly recommend this rental. Large and open, nice deck, great pool and hot tub. Decent gym. Great restaurants north and south. Easy access to bike trails. Pickle ball and tennis court. Jonell was excellent with communication.
Stayed 7 nights in Mar 2023
From a partner site

8/10 Good

Roger D.

Key West Adventure

Rating Details: The property manager was more than helpful. The vacation rental was very clean. 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 took our daughters and spouses and it was perfect for us. The house is beautiful, especially the back outdoor space, which we spent most of our time while there. The pool was right behind us and heated perfectly. My only recommendation would be to have a more comfortable pull out sofa bed.
From a partner site

8/10 Good

Brian A.

Sailors Story

Rating Details: The property manager was adequately 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 do not recommend this vacation rental. Reviewer Comments: This rental was better than previous rentals. The second bedroom is very small and the associated bathroom shower was difficult to stand in. This rental would be acceptable for a week stay. We are disappointed that one week stays may no longer be available. We are not interested in a month rental, so we will be looking for accommodations other than the Truman Annex.
Verified

6/10 Okay

Scott B.

Great place to stay

Overall, we thoroughly enjoyed our stay here and would probably stay again. Great home and very comfortable, with only a few issues that caused minor inconvenience. Supposed to have a grill, but apparently it had been removed and the details had not been updated on HomeAway. This affected our plans for sure and had to find another place to cook all the food we brought. Asked a couple times to have the 2nd bedroom set up as a king. Was still two single beds. Wifi password on either the printed map or sent directly to tenant would have been more convenient than having to call the off hours number. All in all, still a nice property.
Stayed 7 nights in Oct 2018
From a partner site

6/10 Okay

Wayne C.

A Rental With Potential

Rating Details: The property manager was more than helpful. The vacation rental was somewhat dirty. I was more than 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 stayed here before in 2020 and liked it. The unit has a lot going for it-location, nice patio, two baths. The furniture was fairly comfortable, and for TV lovers there is a huge TV--though its difficult to stream as the owners have left their own account info active. Unfortunately, though the regular cleaning staff was thorough, the unit has seen a lot of hard use in the last two years and at a minimum needs a deep cleaning. The sofa and rugs need a good shampooing, etc. Also, the bathrooms are original and show it. The way the kitchen was stocked was odd-lots of some things (like pitchers) but missing other day to day items.
From a partner site

10/10 Excellent

Gisele F.

relaxing stay 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 more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The condo was lovely. The reservation process was super easy. A few things to note - 1- the TV setup is extremely complicated. - They need some instructions also someone needs to check the batteries in all the remotes. 2- The water pressure in the master shower is very slow - 3-Have the ice maker started before you arrive. 4- The sheets could be replaced. Looking a bit wornWe enjoyed our stay. It was very clean - The management was very quick to respond. Did a great job
From a partner site

6/10 Okay

Jennifer C.

Overall Nice but had some issues

Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: Compass was mostly attentive to our needs, but there were a couple of things that didn’t get addressed. Upon our arrival we noticed (as did our family staying nearby) a musty smell as you walked in, not pleasant. We had a shower issue that was addressed after the second email. The home itself was clean and the patio out back gorgeous & private. Construction next door was happening but luckily didn’t dampen our visit that much. Kitchen could do with a little updating but it served our needs. During our stay the pool was full during the day, so we had to resort to going in the evening since it’s small. Which is the case with many properties in key west, as expected.
From a partner site

10/10 Excellent

Deb E.

Sailor’s Story Review March 2024

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: Sailor’s Story is clean and nicely appointed with well stocked kitchen essentials and beach towels for the pool. Location is quiet (sans for the remodeling construction next door) and centrally located with easy access to the pool and main gate. Reserved parking spot is covered and just a few steps away from the unit. I recommend replacing the sleeper sofa as it is broken and mattress too thin for the springs. Also recommend listing HOA rules as we were “cited” for a beach towel drying on the front railing
From a partner site

10/10 Excellent

Bob K.

Feb. 10 -24 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: Very nice stay,great location. Compass folks were great. Only minor issue a few outlets were not working and TV in smaller bedroom. Already booked for next year. Thanks again Bob
From a partner site

10/10 Excellent

Steve S.

Very nice place

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: This place was very nice and clean, great location,parking was good,
From a partner site

10/10 Excellent

Carolyn K.

Key West Trip #6

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: Have rented from Tareci (Compass) for years now and the properties are always clean and in good condition. Very easy and convenient process from start to finish and if there is an issue, someone will answer you promptly!

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