Captain's Wheel at The Truman Annex in Key West

Key West, Florida
$311 avg/night Minimum Stay 28 Nights
Bed 2

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

Night 28 nights

Min Stay

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

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Carport
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Fenced Yard
  • POOL/SPA

    Heated Pool Shared/communal Pool
  • BATHROOMS

    2.5 Bathrooms Bathtub Or Shower Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Cycling Nearby Ecotours Nearby Fishing Nearby Golf Nearby Jet Skiing Nearby Marina Nearby Sailing Nearby Scuba Diving Nearby Water Park
  • ENTERTAINMENT

    Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    In The City Center Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Victoria k.

    Submitted May 15, 2025

    Stayed May 7, 2025

    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.

  • Timothy H.

    Submitted Nov 25, 2024

    Stayed Dec 31, 1969

    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 !

  • Timothy H.

    Submitted Nov 24, 2024

    Stayed Nov 16, 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: Quite surroundings. Sat on the front porch and watched people walk by! Very peaceful !

  • Branden Y.

    Submitted Jul 1, 2024

    Stayed Dec 31, 1969

    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!

  • Erin Z.

    Submitted Apr 22, 2024

    Stayed Apr 13, 2024

    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.

  • Mary alice D.

    Submitted Apr 15, 2024

    Stayed Dec 31, 1969

    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!

  • Eric 8 K.

    Submitted Jan 29, 2024

    Stayed Jan 20, 2024

    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.

  • Brian W.

    Submitted Dec 28, 2023

    Stayed Dec 31, 1969

    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

  • Kelly J.

    Submitted Aug 3, 2023

    Stayed Dec 31, 1969

    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.

  • Cyndie H.

    Submitted Jun 24, 2023

    Stayed Jun 17, 2023

    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!

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Total

Includes taxes and fees
$311+
View details