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800 sq. ft. DISCOUNTED MONTHLY RATES. JANUARY 2026 RENTAL RATE $9598.50. +$220.00 CLEANING FEE AND 12.5% TAX
AMAZING LOCATION in TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all. Large front yard and porch to watch Key West pass by. Beautiful and spacious in/out doors. POOL within 1 walk of condo. We rent for 7 days or more, monthly. Ground Floor for ease and having a beautiful outdoors to enjoy.
120 FIVE-STAR REVIEWS!!! (on our primary site on VRBO #595903)
Book NOW for 2026 DISCOUNTED MONTHLY RATES ! Make the sunny and comfortable Shabby Chicken your monthly destination during 2026.
Our awesome cleaner has been with us for years. Read our reviews on VRBO #595903, historically we always been known to have a spotless and clean place.
5-STAR rating and the best floor plan around. This exceptional, over-sized floor plan 2 bedroom, large bath, full-size kitchen is only offered in a couple of units in the Truman Annex Shipyard. Large deck along with a outdoor patio/dining area. It feels more like a home than a condo. Relax at the Truman Annex Shipyard Pool - which is a minute walk from the condo.
SHABBY CHICKEN BEDROOMS & FLOOR PLAN (Ground Floor)...
The Shabby Chicken has 2 very spacious bedrooms, both with KING beds (or one bedroom can be converted into two twin beds) offering the privacy of each bedroom located on OPPOSITE sides of condo. Each bedroom has a TV, ample room to store clothes.
This exceptional, oversized floor plan is only offered in a couple of units in the Truman Annex Shipyard. The bathroom is also large and has a double vanity, walk-in shower. Our outdoor space is 2-3 times the size of other condos.
Two sets of French doors in the centrally located living room and window in the full-size kitchen provide sunlight and a spacious feeling not found in other units.
LIVING AREA & KITCHEN...
The central living area with new large, leather sectional couch with a full size kitchen provides a great floor plan for 2-4 people. The kitchen is equipped with all new appliances, countertop, modern backsplash and finishes. There is counter-top seating and a large dining table with beautiful lighting and seating for four or more that is stylish and functional.
OUTDOORS...
Two sets of French doors lead to the HUGE, MULTI-SPACE OUTDOORS.
Enjoy morning coffee or an intimate dinner at the comfortable dining table on the large, covered, private deck. Step down to the herringbone brick patio that is able to accommodate a small party to dine alfresco. Or take a relaxing nap or read a book on the lounger under the palm (we're not kidding!). Gas grill on patio.
POOL...
Less than a one minute walk to the pool
AMENITIES...
This ground floor condo is very clean, and has well-appointed bedrooms which have been completely updated with beautiful linens, art work and comfortable beds. A new washer/dryer are located within the unit for your convenience. The fully equipped kitchen with all new appliances, pots & pans, towels & linens and central air conditioning provide all the amenities you want for long- and short-term stays.
You'll also enjoy a 32' flat screen TV in the living room with an Italian-made large, leather sectional. Secure wireless Wi-Fi and and Bluetooth speaker for your device to connect to for music.
Our condo is outfitted with beach towels, beach chairs, a cooler, etc.
PARKING SPOT
We also have on-site parking with your own dedicated parking spot, although it's likely you will not need (or want) to get in your car while you're here.
WHAT MAKES IT SPECIAL...
The Shabby Chicken (for it's shabby chic design) has interesting design elements, such as vintage clocks, modern geometric patterns, original artwork from Cuba and local artists, wood carvings from the Philippines and India, along with beautiful tapestries. The place feels very luxurious, contemporary, and relaxing.
PROXIMITY TO PLACES...
The Shabby Chicken is within easy walking and biking distance to everything Old Town Key West has to offer, including Fort Zachary Beach and a one minute walk to the Truman Annex pool. Walk down to the Truman Annex waterfront to take in a special and low-key sunset for which only the locals know about. Walk or bike through the gorgeous Truman Annex over to happening Mallory Square for shops, museums, and special events.
2023 Updates: All New Highly Insulated Windows and Doors
2022 Completely landscaped front and backyard
2021: New AC
2020: New washer and dryer appliances
2018 Condo Updates: Beautiful walk in shower.
DISCOUNTED MONTHLY RATES.
Cheers! Marie and Tom
Unique Benefits
Our condo is very special with a large floorplan only found in 2 other condos. Truman Annex is a fantastic location in the Heart of Key West historic area.
You'll love our large front porch with huge front yard. The outdoor space is plentiful and multiple seating areas on the backyard with private hedges and lush plants.
Walk 1 block to see a beautiful sunset from the Truman Waterfront Boardwalk!!
The Truman Annex is a coveted historic distric location - close to Duval St., Mallory Square, Zachery Beach, the waterfront for sunsets, and the Green Parrot - you cannot find a more prime location with these amenities anywhere else. You'll love the beautifully landscaped grounds, pool, and access to the waterfront sunsets. The Waterfront Park and amphitheater are a 2-5 minute walk. The Truman Annex is close to the action, but far enough from the riff-raff :)
Within 2-3 blocks of all the attractions, bars, restaurants, parks and sunset by the waterfront and Fort Zachery beach
Yes, I have a recommendation list that I send out for our guests. It's Key West On/Off the Beaten Path.
Yes, I have a recommendation list that I send out for our guests. It's Key West On/Off the Beaten Path.
Washer and Dryer in condo!!
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Nov 29 - Dec 21 2025 | $395 | 7 nights | |||
Dec 22 - Dec 26 2025 | $495 | 28 nights | |||
Dec 27 2025 - Jan 03 2026 | $695 | 28 nights | |||
Jan 03 - Feb 01 2026 | $11,600 | 28 nights | |||
Jun 05 - Jun 30 2026 | $345 | 28 nights |
Fees:
Notes:
Zelle and Venmo electronic payments have NO FEES. Personal checks are also accepted
Upon the last payment, there is a $300 security deposit that is requested. It is refundable upon our cleaning and ensuring all is in good working order.
Weekly stays in 2025 are available.
Monthly 2026 stays and rates are noted online; this is 28 days or more stay at a time. There is a 60 day cancellation policy.
Last updated on October 28, 2025
Tami B.Perfect Getaway
My husband, two grown children, and I had a wonderful week long stay at The Shabby Chicken located in beautiful Truman Annex! The proprietor was amazing to work with! The property was exactly as pictured and the location could not be more amazing! We met lovely people at the communal pool and were a short walk from great bars, beaches, galleries, and shopping. We look forward to staying here again. Absolutely perfect!
Stayed: August 2025 Submitted: August 08, 2025
Matt Y.Not too shabby!
The shabby chicken was exactly as advertised: comfortable, functional and located near the action. The condo is decorated tastefully and while on the first level, it was very quiet and felt private. The upstairs guests foot traffic was sometimes noticeable, but generally was not an issue. The water pressure was a bit lacking, particularly the shower, but we asked the owner and apparently there had been issues the city was trying to address. It never really got much better, however, after bringing it to their attention, but we understand this is island living and is out of much of the owner’s control. We did not use the pool, though we did walk past it just to see it. It’s small, but very functional if you want an alternative to the beach. Zachary Taylor beach is within walking distance, but it’s not a short walk particularly if you are carrying beach gear. Driving is an option though the line of cars trying to enter the park can at times be long. We rented a car and parked in the adjacent lot in the owner’s designated spot (no extra charge). Getting to and from the condo to the car was easy through the back door which is accessible through a shared path that runs along the back of all the condos. The backyard is small, but given the proximity to all the other condos, felt very private. We did see people walking on the shared path from time to time, but again was not excessive or noisy. The beds are firm but comfortable and can be arranged as twins or as a king prior to your arrival. Even though the bedrooms faced the street, we rarely heard traffic or people with the windows shut. One bit of advice: we ran out of toilet paper and ended up buying some at the CVS on Duvall. This isn’t a hotel so some of the things you expect you must take care of yourself. Shampoo and soap bring another amenity you would find at a hotel and some of our party did not bring any which we also purchased. The kitchen has all the essentials and more so if you plan on cooking it more of less feels like home in terms of cookware, dishes and the like. Internet was great and TV service was basic but we weren’t there to watch TV so it wasn’t an issue. Pay particular attention to all of the documentation the owner sends you as it is very good in describing how to check in and out as well as other important information. Overall, we felt the Shabby Chicken was comfortable and provided us with a convenient oasis in the heart of Key West.
Stayed: January 2025 Submitted: January 05, 2025
Host response
"Matt, Thank you for your thorough review of the Shabby Chicken. You summed it up well with our place is comfortable, functional and located near the action. Our place being in the Truman Annex complex is such a gem on the island and having a dedicated parking spot is quite the premium. We hope to hear again from you when the Key West winds call you back down. Cheers, Marie"
Jan P.Love The Shabby chicken
The condo is in great location & close to Duval st, Truman waterfront & Fort Zachary. It’s in a quiet neighborhood with a nice pool area! The condo is well stocked with everything you would need & has comfortable beds & furniture!! Marie is amazing to work with! We have stayed here multiple times & she is always available if you have any questions or concerns!! We highly recommend this condo & hopefully be back next year.
Stayed: December 2024 Submitted: December 14, 2024
Host response
"Jan, Thank you for the glowing review. We are so appreciative of how you mentioned how great the location is, that our neighborhood is quiet and has a pool. Additionally, that our place is comfortable - have a comfortable bed and furniture to lounge is always an important thing after a long day in Key West. Lastly, thank you for saying I'm amazing to work with - this means a lot to me as I've been at this for over a decade and love what I do. Cheers and see you again. Marie"
Terri H.Lovely condo, great location!
My husband and I enjoyed 8 nights in July at the Shabby Chicken. The condo had everything we needed and couldn’t ask for a better location!
Stayed: July 2024 Submitted: August 05, 2024
Host response
"Thank you so much Terri for your review. We're so happy that our condo had everything you needed. You're right the location is unbeatable. Cheers! Marie"
Joseph A.Perfect condo for our needs
Location was perfect as it is closer to the entrance of Truman Annex and in turn only steps away from Duval, Mallory Square and Truman Waterfront park. Owner's were very friendly, extremely responsive and provided excellent instructions for the stay. The condo itself was very clean, spacious and well equipped for our needs. It was a perfect space for "working from home" while mixing in sunshine and relaxation. Highly recommend and will consider for return trips!
Stayed: February 2021 Submitted: March 16, 2021
Host response
"Thank you Joe for your glowing review. I'm so glad you could work from paradise! We appreciate your mention of the perfect location, how clean, spacious and well equipped the condo is. Thank you for your comments on how responsive I am along with the thorough instructions, which include a map, parking info, Wi-Fi, etc are. We look forward to hearing from you when you can get down to the Keys again. Cheers! Marie"
Yes, there is a nice full size washer and dryer located in the condo. We provide you a little detergent, enough for a few loads during your stay.
Yes, we love having guests stay as long as they'd like. We have multi-week and monthly discounts.
Member since 2020
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