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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

A two-story white house with a porch, surrounded by palm trees and a white picket fence.
A coastal hotel with a flagpole, a welcome sign, and a white picket fence.
A swimming pool with blue chairs, surrounded by palm trees and a two-story building with a white fence.
A bedroom with a bed, two bedside tables, a ceiling fan, and large windows with blinds.
A lush garden with various tropical plants and a white fence in the background.

Reviews

9.0 out of 10
Wonderful

Highlights

  • Room to spread out
    Enjoy a spacious layout that gives everyone more room to relax.
  • Onsite parking available
    Convenient and secure onsite parking, a rare amenity in the area.
  • At the center of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Close to Duval Street
2 bedrooms2+ bathroomsSleeps 6

Popular amenities

  • Balcony or patio
  • Waterpark access
  • Swimming pool
  • Internet access
  • Air-conditioning
  • Refrigerator

Explore the area

View in a map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪11 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

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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

Property # 4696494
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. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
View more Holiday homes in Key WestOpens in a new window
Map
Key West, FL

What's nearby

  • Florida Keys Eco - Discovery Center - 3 min walk - 0.3 km
  • 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

Getting around

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

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Margaritaville - ‬7 min walk
  • ‪Moondog Cafe & Bakery - ‬8 min walk
  • ‪Mangoes Restaurant - ‬7 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 6 Sept, 2026, prices found for a 1-night stay for 2 adults at Captain's Wheel at The Truman Annex in Key West on 15 Sept, 2026 start from S$12,049, 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.

About the host

Hosted by Compass Realty Vacation Rentals & Property Management

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Languages:

English

Premier Host

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