Ground-floor Old Town condo with a private wooden deck. Parking at your door. 28-night minimum.
Key West Charming is a 2-bedroom, 1-bath first-floor condo in the Shipyard section of Truman Annex close enough to Duval Street to walk to anything, far enough that you won't hear the noise from your deck. Lovingly maintained by the owners and built for extended stays of a month or more.
Monthly rates range from $3,900 (June) to $13,000 (February). Full breakdown below.
Note: The Shipyard community pool will be closed Aug 1 Sep 1, 2026 for deck replacement. If your stay overlaps, the pool will be unavailable during that window.
Inside
- Single-level ground-floor layout no stairs
- Open living and dining area flowing out to the back deck
- Two bedrooms, one full bath (queen in primary, two twins in second)
- Twin beds convert to a king on request ($75, 48hr notice)
- Well-equipped kitchen with everything you need to cook
- In-unit washer and dryer
Outside
- Large private wooden deck off the living area sun, privacy, and room to relax
- Shared community pool with palm-shaded paths and landscaped grounds
- Assigned parking spot directly in front of the unit door
The location
Truman Annex is gated, walkable, and a few minutes from everything that makes Key West Key West. Walk or bike to Duval Street's shops, galleries, and restaurants. Steps to Fort Zachary Taylor State Park (the island's best beach and sunset spot). A short walk to Mallory Square's nightly sunset celebration, the Hemingway House, and Truman Little White House.
Concierge service
Stays include access to AvantStay's concierge fridge stocking, private chefs, transportation, beach gear, and special occasion planning, all on request.
Monthly rates:
- June 2026 - $3,900
- July 2026 - $4,800
- August 2026 - $5,900
- September 2026 - $5,700
- October 2026 - $7,400
- November 2026 - $9,300
- December 2026 - $9,900
- January 2027 - $11,800
- February 2027 - $13,000
- March 2027 - $11,800
- April 2027 - $7,000
- May 2027 - $6,000
The fine print
- 28-night minimum stay
- Stays of 28+ nights require additional scheduled cleanings (billed separately based on length of stay)
- Security deposit required for all 28+ night bookings
- Max occupancy includes infants
- One assigned parking space; no guest parking. Vehicle size limit: 18' long, 80" wide. No trailers, RVs, vans, or campers. Truman Annex parking pass required.
- Service/ESA animals: documentation may be required for entry
- Key West wildlife (geckos, lizards, frogs, chickens) and seasonal insects are part of life on the island; the unit is on a monthly pest control schedule
- Construction and road work in Old Town can occur without notice; AvantStay is not liable for related disruptions
Reach out with your dates, and we'll confirm availability and walk you through the next steps!
Apartment amenities
Property amenities
Air Conditioning
Bakeware
Basic Cooking Essentials
Beach
Beddings and Sheets
Ceiling Fan
Cleaning Supplies
Cookware (Pots, Pans, Cutting Boards, Knive...
Deadbolt Lock
Dinnerware (Bowls, Plates, Mugs)
Dishwasher
Downtown
Drip Coffee Maker
Dryer
Fire Extinguisher
First Aid Kit
Freezer
Garden/Backyard
Glassware
Ground Coffee & Tea
Hot water included in rent
Kitchen
Kitchen Cleaning Supplies
Laptop Friendly Workspace
Laundry: In Unit
Laundry: Shared
Outdoor Dining Area
Oven
Patio
Patio Balcony
Pillows and Blankets
Private Entrance
Refrigerator
Serveware
Silverware (Forks, Spoons, Knives)
Smartlock
Smoke Detector
Stove
Swimming Pool
TV
Towels
Travel-Sized Toiletries (Shower Gel, Shampo...
Washer
Water Filter
Wifi
Pet policy
No cats allowed
No dogs allowed
Pricing comparison
$583
At $3,900, this listing is priced $583 cheaper than the current market rate for a 2 bedroom home in Bahama Village.
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