Located in the heart of Key West's downtown, this charming home at Key West Charming offers a warm welcome with a private wooden deck perfect for sunbathing. Within walking distance to Fort Zachary Taylor State Park and Duval Street, enjoy restaurants, bars, galleries and Sunset Celebration at Mallory Square. A well-equipped kitchen makes meal prep easy and the community swimming pool is great for soaking up the afternoon sun.
Reviews
9.09.0 out of 10
Wonderful
Entire home
2 bedrooms1 bathroomSleeps 460 sq m
Popular amenities
Pool
Kitchen
Washing machine
Dryer
Free Wi-Fi
Air-conditioning
Add dates for prices
About this property
Communal Pool | Gated Community | Month-Long Stays | Key West Charming
*Please note that this home is available for 28+ night stays only.*
PLEASE READ PRIOR TO BOOKING THIS PROPERTY: The Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests. *The rates for the month of August have already been discounted to reflect the loss of the amenity.*
Located at the Shipyard Condominiums downtown Key West, this first floor, 2 bedroom, 1 bathroom home has been lovingly cared for by the owners. The living and dining area opens to a large wooden deck in the backyard to relax and soak up the sun in privacy.
The master bedroom has a queen-size bed. The second bedroom has 2 twins. The bathroom is conveniently located in the hallway between the two. A well-equipped kitchen makes any meal you prepare a breeze.
Key West Charming offers the benefit of a great downtown location, within walking distance to all the sights and attractions including Fort Zachary Taylor State Park with one of the nicest beaches on our island. The property is just minutes from Duval Street with restaurants, bars, galleries, tourist attractions, and Sunset Celebration at Mallory Square.
Ride your bike or walk through the beautiful Truman Annex. Play all day out and around town or soak up the afternoon sun at the community swimming pool. Perfect for a couple or a small family.
Key West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!
*Home Truths:* - This home has access to a shared pool. - This home is part of a gated community. - Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay. - All bookings 28 days or longer require a security deposit to be charged after booking. - This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area. - Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area. - We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet. - Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance. - Please note that max occupancy includes infants. - Please be advised that documentation may be necessary for ESA/service animals to gain entry. - PLEASE READ PRIOR TO BOOKING THIS PROPERTY: The Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests.
Parking Details: - One parking space per unit, no guest parking. - No vehicle over 18’ long or 80” wide allowed. - No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex. - Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches. - All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse). - All others will be subject to ticketing and towing.
---
The room configuration is as follows:
Primary Bedroom / Queen bed Bedroom 2 / Two twin beds
---
This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.
As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.
Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees.
There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.
As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.
IDs will be requested for verification after booking.
We report and prosecute all Credit Card Fraud.
Property amenities
Beach
Beach nearby
Pool/Spa
Communal pool
Internet
Available in the house: Free WiFi
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Oven
Refrigerator
Bedrooms
2 bedrooms
Bedsheets provided
Bathroom
1 bathroom
Bathtub or shower
Hair dryer
Towels provided
Entertainment
Smart TV
Outdoor areas
Garden
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Pets
Service animals only (pets not allowed)
Suitability/Accessibility
Smoke-free property
Location highlights
In the city centre
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
Deadbolt lock
General
Garden
Gated community
Unit size: 646 square feet
Similar properties
Key West Casa | Pool Access | BBQ & Patio | Near Duval Street | Month-Long Stays
Old Town Key West
Key West Casa | Pool Access | BBQ & Patio | Near Duval Street | Month-Long Stays
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets not allowed (service animals are welcome, and are exempt from fees)
Children and extra beds
Children are welcome
Events
No events allowed
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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
About the area
Located near the beach, this holiday home is in Old Town Key West, a neighbourhood in Key West. Southernmost Point and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting. Visit our Key West travel guide
Does Communal Pool | Gated Community | Month-Long Stays | Key West Charming have a pool?
Yes, this property has a pool.
Is Communal Pool | Gated Community | Month-Long Stays | Key West Charming pet-friendly?
No, only service animals are welcome at the property.
What time is check-in at Communal Pool | Gated Community | Month-Long Stays | Key West Charming?
Check-in begins at 4:00 PM.
What time is check-out at Communal Pool | Gated Community | Month-Long Stays | Key West Charming?
Checkout is at 10:00 AM.
Where is Communal Pool | Gated Community | Month-Long Stays | Key West Charming 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.
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Communal Pool | Gated Community | Month-Long Stays | Key West Charming Reviews
Reviews
Wonderful
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Great location. Quiet area but close to everything.
Daniel A.
Stayed 7 nights in Feb 2025
Verified
10/10 Excellent
Debra B
4 Jan 2024
Liked: Cleanliness, amenities, property conditions & facilities, communication
Any issues were handled immediately and followed up to make sure everything was good. The home was immaculate and so comfortable. Kitchen was a little small but had everything we needed to prepare meals. Would absolutely stay again.
Debra B
Stayed 7 nights in Dec 2023
From a partner site
10/10 Excellent
Cliff M.
27 Aug 2021
Great location, comfy digs!
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:
Everything about the property was first rate. The location is ideal for walking or touring the town.
Cliff M.
From a partner site
10/10 Excellent
A guest from Webster, NY
25 Oct 2021
October 2021
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:
Great time,
A guest from Webster, NY
From a partner site
10/10 Excellent
A guest from CARLISLE, PA
5 Oct 2021
A fantastic location
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:
Our rental was well appointed with many items that aren't always found in many rentals. The location was fantastic! Being right in Old Town made it very easy to walk to most of what we wanted to see.
A guest from CARLISLE, PA
From a partner site
8/10 Good
Kathy O.
13 Dec 2021
Nice 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 satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
The location is very convenient. The swimming pool was steps from our condo. Condo was very clean and lots of towels and everything that we needed. It was a bit dated, but the back patio was beautiful.
Kathy O.
From a partner site
10/10 Excellent
Lisa C.
30 Dec 2021
Ontario Hot Chicks Key West December 2021
Rating Details:
The property manager was more than 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:
Excellent!! Great location!! Great Back Yard!!!! Need plastic//acrylic glasses for pool area
Lisa C.
From a partner site
10/10 Excellent
A guest from Weirton, WV
25 May 2021
Cute place in Truman Annex
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:
Very clean and location was prime. Everything you need , washer & dryer , coffeemaker, towels, blankets in closet and hangers. Patio had table and chairs with beautiful plants and flowers surrounding the area. Was a comfortable stay
A guest from Weirton, WV
Archival
10/10 Excellent
Wayne B.
29 Nov 2015
FANTASY FEST WEEK
Place was clean, quite, easy access to Duval Street. Only had a problem with washing machine that was fixed with just one phone call on Fantasy Fest Friday. Got my security deposit returned in less than 3 weeks.
Wayne B.
Stayed 7 nights in Oct 2015
From a partner site
10/10 Excellent
Jennifer S.
18 Jan 2021
Quiet getaway close to Duval St.
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:
This was a nice getaway place to stay with our two young adult children. We wanted a place with two bedrooms and separate beds in the second bedroom. The living room furniture was not very comfy as the sofa is a hid-a-bed, but we didn't spend much time there. The beds were comfortable with a firm mattress in the master. Kitchen is supplied with the basics. Complex is quiet and well-maintained. Walking distance to Duval Street, Fort Zachary Taylor Historic State Park and Beach, bars/restaurants, and many other destinations on Key West.
Jennifer S.
From a partner site
10/10 Excellent
Stephen Z.
4 Mar 2021
Key West Charming
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:
The condo is comfortable and clean. It is well located to walk to restaurants, bars, and points of interest. The TV was very old and the picture was stretched and not in focus. We contacted At Home in Key West to report the problem and were pleasantly surprised to have a new TV installed three days later thanks to Jessica Robb, who was so knowledgable, professional, and efficient in installing the new TV. We were thrilled that we were able to stream shows using the new TV.
Stephen Z.
Verified
8/10 Good
Curt W.
20 Mar 2018
Nice location, on the quiet side of the property
The location is on the quiet side of the property and the parking space is right in front of the unit. The small kitchen is well supplied and has been updated. The bathroom is very small. The main bedroom has a queen size bed and two twins in the second room. The furniture in the living room is dated as is the outdoor furniture. The unit was clean, plenty of towels were provided and having the washer/dryer was great. They provided enough bathroom/kitchen/detergent supplies for a one week stay. Missing is a barbeque, lounge chairs for outside and there are not any bikes or beach items. Since all local beaches require you to pay for umbrellas and chairs ($10 each) it would be nice if some items were provided at the unit. Others we have stayed in do provide those items. It was our second time at Truman Annex and the location is really the positive attribute if you like to walk to Duvall Street, Mallory Square, restaurants, museums and shopping. The downside is a very small, crowded pool and it is quite a distance from the beaches so you need bikes, a car or a moped. Overall, our stay was very nice.
This property is in an absolutely perfect location. We loved our stay here! Only complaints: We had to check in and check out at a location offsite, which is inconvenient. I would have preferred a key pad at the property like many places do—although the staff at the office were immensely kind and hospitable. Also, the queen size bed wasn’t comfortable, so my husband and I slept in the two twins. The kitchen was certainly a plus, but it could use some replenishing of pans and cooking utensils. Water pressure in the shower was amazing!! Again—perfect location!! I certainly would not hesitate to stay here again. Amazing times!
Amy B.
Stayed 7 nights in Mar 2022
From a partner site
8/10 Good
Diane T.
14 Feb 2022
great location
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
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:
Very clean, great location, great management company. Outdoor patio chairs are old and don't fit the table but minor concern. Everything was very comfortable. Would rent again!
The place was as advertised. Property is conveniently located near Duval Street.
The only issue we had with the stay was the Wi-Fi. Reception was nonexistent at worst and poor at best. Do not plan to work remotely from this stay…enjoy your vacation instead.
Signed,
A Serious Workaholic
The unit was nice, clean and suitable for accommodations.
I had a BIG problem with the parking situation. I understand we couldn’t park our F350 there since it is 20’ long. But my problem was we had 2 golf carts and had passes for both from security. We parked both in our parking space, but received a ticket. They said we could only park 1 golf cart in the space. We paid for the space and we were not outside the parking space. They said it didn’t make a difference. We will probably NEVER stay at the Truman Annex again. The security guards are terrible. They think they have all the authority to do what they want you to do. They were VERY ARROGANT! If I had people like that working for me,, they wouldn’t work very long. I did not see anything in the paperwork that said we couldn’t park 2 golf carts in our space. It is a good way to make people stop staying at the Truman Annex. For the price we paid, we should have been able to provide parking for our Golf carts.
This was a great property located in a wonderful section of Old Town Key West. Convenient to many attractions. Neighbors nearby were extraordinarily friendly. We enjoyed spending our mornings out on the patio drinking coffee and pine or day before heading out to see the local attractions. Would definitely recommend.
Robert H.
Stayed 7 nights in Jan 2020
Verified
8/10 Good
Carrie K.
1 Apr 2018
Great little hideaway.
The property is really cute, clean and very conveniently located. We had a few maintenance issues during our stay, but the staff was super responsive and did everything they could to minimize inconvenience. Thanks Brigit and Samantha!