CAPTAIN'S WHEEL

This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home featuring an open floor plan with a great rear deck for entertaining and relaxing. The master bedroom has it's own balcony and the guest bedroom features a covered porch offering plenty of outdoor living. This opportunity also includes a carport and a convenient community pool. The President's Walk area of the Truman Annex is located on Southard Street and this particular gem is perfect for both people watching and the best view of several local parades. Complete with updated appliances, 2 TVs, Wi-Fi and a lovely landscaped front and backyard. A perfect little slice of Paradise.

Please note: This property has a 28 night minimum stay

Vacation Rental Reviews

• Wonderful Week

  Stayed 7 days ending in May, 2025

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  Victoria k from Windsor, CO recommends this vacation rental

  We stayed in Captains Wheel for a week. There were four of us and plenty of room. The location is excellent. Close to Duval Street and everything else but also quiet. Absolutely beautiful area. The house itself could use some work and updating.. broken blinds, dirty yard, old mattresses, broken drawers on dresser. The management staff was quick to respond with questions and concerns.

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• 1 month in paradise

  Stayed 35 days ending in February, 2025

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  Lisa D from Fairfield, CT recommends this vacation rental

  5 weeks in paradise. Mostly. Could not beat the central location to everything. Had a wonderful time overall. Wish we were made aware of construction on the unit next to us that began at 8:30. Woke us most mornings. And when on vacation that's not what you want to happen. Also southard is extremely busy due to construction occurring at the park. Very loud. If you want quiet and peaceful do not stay on Southard for now. Or at least until they finish construction. Unit could use updating but was fine for our needs. Again. Location location location.

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• Key West Vacation

  Stayed 7 days ending in November, 2024

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  Timothy H from Elk River, MN recommends this vacation rental

  Quite surroundings. Sat on the front porch and watched people walk by! Very peaceful !

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• Great Place!!

  Stayed 7 days ending in June, 2024

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  Branden Y from Lebanon, OH recommends this vacation rental

  This place is amazing. From the location to the folks at Compass. We stay every year and this year was the same amazing experience e we always get! Thanks!

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• Let West never disappoints

  Stayed 7 days ending in April, 2024

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  Erin Z from Woodbridge, VA recommends this vacation rental

  We stayed at Captains Wheel in Truman Annex for a week in April. Of course the location is perfect ...everything in Old Town/Historic KW within walking distance, and Mallory Square is just down the street...seriously. We arrived on a Saturday and retrieving keys to the TH was super easy and convenient. We absolutely loved the unit! Clean, stocked with just about everything we needed. Beds were comfortable as was the furniture in the LR. A balcony off each BR makes for great morning to drink your beverage of choice. Loved the community pool as well! Truman Annex in general is just beautiful and quiet too! I will definitely will be returning to KW and Truman Annex will be where I stay again. I’m already missing the Palm Trees ��
  One final thing...the staff at Compass was great! They made the checking in and out process super easy.

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• Perfect!!!

  Stayed 56 days ending in March, 2024

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  Mary Alice D from West Hartford, CT recommends this vacation rental

  Lucky to be there!

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• Key West Vacation

  Stayed 7 days ending in January, 2024

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  Eric K from Rockford, MI does not recommend this vacation rental.

  Cozy, clean place, 2 bedrooms, 2.5 baths. Nice private patio with grill. Great location and easy to walk to all points on Key West.
  Cons: Construction next door made it difficult to enjoy patio (main off living room and bedroom) with construction activity and noise going on during the day. Find it odd we weren't notified or at least an apology note. I've stayed a lot of places and construction does happen, but company/management always up front about it and try to make it right.
  Beds: Very old, worn and need to be replaced. Others and I woke to back pain daily. All pillows were firm with no other options available.
  Bedroom bathrooms need to be upgraded. Nearly impossible to turn on one of faucets and non-stop dripping of shower/tub.
  With the current condition of bedrooms, I wouldn't recommend this location or stay there again until issues addressed. The Truman Annex is a perfect location with a lot of natural beauty. There are several other properties to choose from.

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• Great overall property

  Stayed 10 days ending in December, 2023

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  Brian N from Windsor Locks, CT recommends this vacation rental

  Roomy and in a great location
  A little extra pre-arrival inspection would be nice to ensure all electronics and battery operated systems are working correctly

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• Captains Wheel

  Stayed 9 days ending in July, 2023

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  Kelly J from Naples, FL does not recommend this vacation rental.

  We Enjoyed our stay at The Captain's Wheel, however This property is just OK stocked primarily in The Kitchen. No hot pads, washcloths, kitchen towels or cleaning supplies etc. Beds need to be upgraded too. The Queen bedded room is only good for sleep. My husband and I kept sinking into the middle. The other twin bedded room the mattresses are so hard/stiff. I think beds are so important & that is why I would not recommend to family or friends. A little bit of tweak would bring this property to five stars.
  

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• Perfect Key West Location

  Stayed 7 days ending in June, 2023

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  Cyndie H from Mountain City, TX recommends this vacation rental

  We had a great time staying in this rental. It was comfortable and in a great, nice location.

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• Great place to stay

  Stayed 7 days ending in May, 2023

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  a guest from DELPHI, IN recommends this vacation rental

  Great place to stay, great location centrally located near Duval st. Lots of room. Nice little pool that was not over crowded.

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• Nice stay in Key West

  Stayed 7 days ending in December, 2022

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  Robert C from Lakewood, NJ recommends this vacation rental

  Trumann Annex is in a great location in Key West. We were 2 short blocks from Duvall which made it convenient but far enough away for no disturbance. Each day we would take our 1 mile walk down Duvall over to the Galleon where our friends had their boat docked and another who was staying at the Galleon. The unit we stayed in was clean and had everything we needed but the bedding needs to be replaced as the MBR bed was uncomfortable. The unit could also use some updating. Other than that it had everything we needed.

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• An Excellent Rental

  Stayed 7 days ending in December, 2022

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  Brian N from Windsor Locks, CT recommends this vacation rental

  Wonderfully located and has anything you might need. I don’t know about high season, but it was quiet and there were no problems. As usual for a Compass rental

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• Short Paradise Stay

  Stayed 7 days ending in October, 2022

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  Keith B from New Port Richey, FL does not recommend this vacation rental.

  THe unit itself was very mediocre. Of all the units we have stayed in the Truman Annex, this was by far the worst. And we were there only one night due to Hurricane Ian. We had lighting that did not work, tv that did not work, floors dirty, etc etc. The only reason to stay here again would be to use up the time that the staff graciously gave to us due to the weather conditions. I would much rather stay in another unit.

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• Fun in the Keys!!

  Stayed 7 days ending in July, 2022

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  Edmund T from ALMA, GA recommends this vacation rental

  We had a really great time.

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• Nice locaction

  Stayed 7 days ending in June, 2022

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  Jennifer M from TOLEDO, OH does not recommend this vacation rental.

  The location of this rental is within walking distance of Duval street, Mallory Square and many other places. The only problem with this rental is the sleeping arrangements, the pictures show what appears to be large beds in both bedrooms. However, one bedroom has 2 twin size beds which are hard, and the bedroom that does have a queen size bed the mattress has you rolling into each other in the center. The unit does have a washer/dryer unit which was convenient.

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• Excellent stay and location

  Stayed 7 days ending in May, 2022

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  Tina S from New Smyrna Beach, FL recommends this vacation rental

  This is our 6th stay at the Truman Annex thru Compass Realty and our 2nd stay at this same unit. Excellent service and will continue to be a repeat customer.

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• Captains Wheel New Years

  Stayed 7 days ending in January, 2022

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  Deanna S from Chattanooga, TN recommends this vacation rental

  Very nice! We have stayed in the Truman Annex many times but this was the first time of being on the main road into Truman Annex. We stayed in the front bedroom and the traffic noise was pretty bad. Also, the pools in Truman are just too small. Large families staying come and take over the pool. I know this is the busiest time of the year, but they were both very crowded.

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• My daughter wedding

  Stayed 7 days ending in December, 2021

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  a guest from Sterling, VA recommends this vacation rental

  It was good. The property needs some work.I hate being in vacation have someone in my place fixing stuff with out letting me know earlier that would happen.

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• Key West Dream

  Stayed 7 days ending in December, 2021

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  a guest from Cheshire, CT recommends this vacation rental

  Wonderful location- a close walk to Duval St and Z. Taylor beach. Lovely setting in Truman Complex. Unit was clean and nicely furnished. Happily surprised to see washer/dryer. Hope to return again next year!

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• November 2021

  Stayed 7 days ending in November, 2021

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  Margaret H from Elizabethtown, PA does not recommend this vacation rental.

  23rd year vacationing in Key West. Always hate to leave. Have highest regard for Compass Realty. This unit is not well maintained.

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• Captains Wheel Truman Annex in Key West

  Stayed 7 days ending in September, 2021

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  Suzanne R from Mechanicsburg, PA recommends this vacation rental

  This was our 2nd stay at Captains Wheel. Compass Realty was fantastic at managing the property. It is a very nice and clean townhouse to stay in. Great location to downtown and to Fort Zachary Beach. Quiet in the evening. In walking distance to mist everything!

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• Amazing time !!!

  Stayed 8 days ending in May, 2021

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  Glenn S from Tampa, FL recommends this vacation rental

  Place is perfect, great location, walking distance to most everything. House has everything you need for a great vacation stay.

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• A great week in Key West

  Stayed 7 days ending in May, 2021

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  Robert R from Leesburg, VA recommends this vacation rental

  We loved this property! Location was great, super clean and the beds were comfy! Highly recommend!

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• Captains Wheel Stayq

  Stayed 7 days ending in January, 2021

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  a guest from Ocean City, NJ recommends this vacation rental

  We had a great overall experience with our stay. We found the house clean and in good condition.
  The bathrooms are a bit small and the appliances could use an update but are in good working order.
  

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• Truman Annex

  Stayed 7 days ending in October, 2020

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  Chrystine P from West Brookfield, MA does not recommend this vacation rental.

  The unit needs some serious updates. The beds(and we tried all 4 sleeping areas) are horrible! The pillows, just as bad! The dishwasher is ancient. There are broken things in the unit, routine maintenance would have found, The area rugs appear dirty. We are in the real estate business, you must put back into your property what you expect to get out of it. The location was wonderful!

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