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Captain's Wheel at The Truman Annex in Key West

Photo gallery for Captain's Wheel at The Truman Annex in Key West

Living area
Exterior
Exterior
Private kitchen
Private kitchen

Reviews

9.0 out of 10
Wonderful
2 bedrooms2+ bathroomsSleeps 6

Popular amenities

  • Heated pool
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony

Explore the area

View map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪13 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area

About this property

Captain's Wheel at The Truman Annex in Key West

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

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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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
On-site 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 that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Key West

Located by the sea, this holiday home is in Old Town Key West, a neighbourhood 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. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
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Map
Key West, FL

What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Duval Street - 6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum - 8 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 14 min walk - 1.2 km

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Rams Head Southernmost - ‬7 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk

Frequently asked questions

Does Captain's Wheel 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 Captain's Wheel at The Truman Annex in Key West?

As of 23 April 2026, prices found for a 1-night stay for 2 adults at Captain's Wheel at The Truman Annex in Key West on 1 May 2026 start from NZ$400, 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 Captain's Wheel at The Truman Annex in Key West pet-friendly?

No, pets are not allowed at this property.

How much is parking at Captain's Wheel at The Truman Annex in Key West?

On-site parking is available at the property.

What time is check-in at Captain's Wheel at The Truman Annex in Key West?

Check-in begins at 4:00 PM.

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

Checkout is at 10:00 AM.

Where is Captain's Wheel at The Truman Annex in Key West located?

Located in Old Town Key West, this holiday home 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.

Reviews

9.0

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 23 out of 38 reviews
Rating 8 - Good. 10 out of 38 reviews
Rating 6 - Okay. 4 out of 38 reviews
Rating 4 - Poor. 1 out of 38 reviews
Rating 2 - Terrible. 0 out of 38 reviews

9.2/10

Cleanliness

9.6/10

Check-in

9.0/10

Communication

10/10

Location

9.2/10

Listing accuracy

Reviews

From a partner site

10/10 Excellent

Timothy H.

Key West Vacation

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

10/10 Excellent

Cyndie H.

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

Wonderful

Great location and clean condo. Couldn’t navigate the tv but not a big deal on vacay. No kitchen linens but paper towels and bathroom hand towels sufficed. Rental co was great to work with on our early arrival and late departure. Location was fantastic!
Stayed 7 nights in Jun 2023
Response from VrboOwner on 14 July 2023
Thanks for staying with Compass Realty! Please let us know next time about the kitchen towels and we will bring some right over.
Verified

6/10 Okay

Chrystine P.

Liked: Location, listing accuracy

TRUMAN ANNEX

THE PROPERTY NEEDS UPDATES, BEDS ARE HORRIBLE!!
Stayed 7 nights in Oct 2020
Response from VrboOwner on 15 December 2020
Thank you for your feedback...we regret you did not like the beds...being that this property is very popular in our program, we have taken the time to poll our last 10 groups of guests and they were satisfied with their recent stays in this home. We can offer you a 10 percent discount on a future booking with us in a different property ? We have been managing over 100 of these properties in the Truman Annex for over 25 years and you would have plenty to choose from... please consider us again. Best, Compass Realty
From a partner site

8/10 Good

Victoria k.

Wonderful Week

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 recommend this vacation rental. Reviewer Comments: 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.
From a partner site

8/10 Good

Ella K.

My daughter wedding

Rating Details: The property manager was adequately helpful. The vacation rental was spotless. I was more than 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 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.
Verified

10/10 Excellent

Randall M.

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

Truman Annex

We have stay at the property before. We love the location of this condo. The floors were a little dirty but everything else was clean. The lamps in the back bedroom needs replaced or rewired. One lamp the wire was twisted up and electrical tape on it. Definitely not to code. The two plugs also need’s replaced as nothing would stay in them. Overall it’s a great place and we will stay there again
Stayed 7 nights in Jun 2023
Response from VrboOwner on 20 June 2023
Hi Randall! Thank you for bringing these items to our attention. I have notified housekeeping regarding the floors and had them replace the lamp. We also have the electrician coming out to fix those outlets. Please keep in mind next time you stay with us that I can have anything remedied while you are here, as to make your stay perfect! We sincerely hope you can stay with us here at Compass Realty again soon!
From a partner site

10/10 Excellent

Erin Z.

Let West never disappoints

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 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.
Stayed 7 nights in Apr 2024
Response from VrboOwner on 23 April 2024
Erin thank you for this wonderful review, we are so glad you enjoyed your stay with us here at Compass Realty and hope to host you again next time you visit the island!
From a partner site

10/10 Excellent

Timothy H.

Key West Vacation

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: Quite surroundings. Sat on the front porch and watched people walk by! Very peaceful !
From a partner site

10/10 Excellent

Branden Y.

Great 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: 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!
From a partner site

10/10 Excellent

Mary alice D.

Perfect!!!

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: Lucky to be there!
From a partner site

6/10 Okay

Eric 8 K.

Key West Vacation

Rating Details: The property manager was more than helpful. The vacation rental was spotless. I was more than 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: 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.
Stayed 7 nights in Jan 2024
From a partner site

10/10 Excellent

Brian W.

Great overall property

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: 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
From a partner site

10/10 Excellent

Kelly J.

Captains Wheel

Rating Details: The property manager was very helpful. The vacation rental was 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: 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.
From a partner site

10/10 Excellent

A guest from DELPHI, IN

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

8/10 Good

Robert C.

Nice stay in Key West

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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.
From a partner site

10/10 Excellent

Brian W.

An Excellent Rental

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: 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
From a partner site

4/10 Poor

KEITH B.

Short Paradise Stay

Rating Details: The property manager was adequately helpful. The vacation rental was somewhat dirty. 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 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.
From a partner site

10/10 Excellent

Edmund T.

Fun in the Keys!!

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: We had a really great time.
Verified

6/10 Okay

Jennifer M.

Liked: Cleanliness, check-in, communication, location

Good location

This property is not exactly how they show it, on room has queen size bed however the mattress has you both rolling into each other in the center. The other room which is pictured as large bed is actually 2 twin size beds, not exactly the most accommodating for a married couple. The fact that it had a washer/dryer on sight was nice. And the property is within walking distance to a lot of destinations.
Stayed 7 nights in Jun 2022
From a partner site

10/10 Excellent

Glenn S.

Amazing time !!!

Rating Details: The property manager was very 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: Place is perfect, great location, walking distance to most everything. House has everything you need for a great vacation stay.
From a partner site

6/10 Okay

Chrystine P.

Truman Annex

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was very dissatisfied with the condition of the vacation rental. Overall, I do not recommend this vacation rental. Reviewer Comments: 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!
From a partner site

10/10 Excellent

Captains Wheel Stayq

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: 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.
From a partner site

10/10 Excellent

Captains Wheel Truman Annex 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 very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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!
From a partner site

8/10 Good

Margaret H.

November 2021

Rating Details: The property manager was very helpful. The vacation rental was very 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: 23rd year vacationing in Key West. Always hate to leave. Have highest regard for Compass Realty. This unit is not well maintained.
From a partner site

8/10 Good

Deanna S.

Captains Wheel New Years

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 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.

About the host

Hosted by Compass Realty Vacation Rentals & Property Management

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