Located in Old Town Key West, this vacation home is within a 10-minute walk of popular sights such as Duval Street and Ernest Hemingway Home and Museum. The vacation home includes a kitchen, a patio, and a refrigerator.
Ernest Hemingway Home and Museum - 6 min walk - 0.4 miles
Duval Street - 6 min walk - 0.4 miles
Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles
Mallory Square - 11 min walk - 0.6 miles
Southernmost Point - 14 min walk - 0.8 miles
Getting around
Key West Intl. Airport (EYW) - 15 min drive
Restaurants
Margaritaville - 7 min walk
Blue Heaven - 8 min walk
Green Parrot Bar - 6 min walk
Bourbon Street Pub - 8 min walk
Mangoes Restaurant & Island Cuisine - 7 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Key West Charming by AvantStay | CommunalPool | GatedCommunity | Week Long Stays
Roof replacement project in Shipyard is scheduled to start on March 28, 2025, and is expected to take approximately 8-9 months to complete. While work is ongoing, residents and guests may remain in their units, as all units will remain accessible. However, please be aware that there will be noise and construction activity during work hours. The work is done in sections so not all properties will be affected at the same time. Please contact AvantStay for more information regarding the approximate schedule for your unit.
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for stays of 28+ days only.*
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.
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.
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The room configuration is as follows:
Primary Bedroom / Queen bed Bedroom 2 / Two twin beds
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Accidental Damage Protection: A non-refundable accidental damage protection plan has been included in the price of your reservation. Under this plan, you will not be held responsible to pay for accidental damage or loss to the rental property resulting from you or others in your party up to $2000. This plan does not cover intentional acts of a guest, gross negligence, or willful and wanton conduct, and/or damages caused by pets. This plan is not available for reservations 28 days or longer or reservations that require a security deposit.
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.
The vacation home is air-conditioned and features a kitchen and a patio, and there's space to spread out with 2 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine and a coffee maker.
Property manager
AvantStay
Languages
English
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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
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Pets
Service animals exempt from fees
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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
Check-in: 4:00 PM
Check-out: 10:00 AM
Minimum check-in age: 25
We should mention
Details about charges, deposits, or other important information:
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.
Property is also known as
62f5f566-de0d-11ec-92c4-c768cd68ffab
Frequently asked questions
What is there to do around this vacation home?
This vacation home is situated in Old Town Key West within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. You'll also find Mallory Square and Fort Zachary Taylor Historic State Park less than a mile away.
Will I be able to park at this vacation home?
No, there isn't parking at this vacation home.
Is this vacation home adjacent to a casino?
No, this vacation home is not connected to a casino.
Will I find an indoor pool at this vacation home?
No, there is no indoor pool at this vacation home.
What amenities will couples enjoy at Key West Charming by AvantStay | CommunalPool | GatedCommunity | Week Long Stays?
Couples staying at this vacation home will appreciate amenities like a kitchen and a smart TV as well as a garden.
Does Key West Charming by AvantStay | CommunalPool | GatedCommunity | Week Long Stays have a hot tub?
No, there isn't a spa tub at this vacation home.
Does this vacation home include breakfast service?
No, this vacation home doesn't offer breakfast.
Will this vacation home allow pets to stay free of charge?
No, pets aren't allowed at this vacation home though service animals are welcome.
Does this vacation home have connecting rooms?
No, this vacation home doesn't feature connecting guestrooms.
How far is the airport from this vacation home?
The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 4.1 mi away (15 minutes by car).
Are there rooms with balconies at Key West Charming by AvantStay | CommunalPool | GatedCommunity | Week Long Stays?
Yes, every accommodation at Key West Charming by AvantStay | CommunalPool | GatedCommunity | Week Long Stays comes with a deck.
Key West Charming by AvantStay | CommunalPool | GatedCommunity | Week Long Stays Reviews
Reviews
9.0
Wonderful
All reviews shown are from real guest experiences. Only travelers 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.
Rating 10 - Excellent. 14 out of 21 reviews
10 - Excellent
14
Rating 8 - Good. 5 out of 21 reviews
8 - Good
5
Rating 6 - Okay. 1 out of 21 reviews
6 - Okay
1
Rating 4 - Poor. 0 out of 21 reviews
4 - Poor
0
Rating 2 - Terrible. 1 out of 21 reviews
2 - Terrible
1
9.4/10
Cleanliness
10/10
Amenities
10/10
Property conditions & facilities
10/10
Eco-friendliness
Reviews
10/10 Excellent
Zachary L.
Jul 3, 2025
Liked: Cleanliness
Key west vacation
Very clean and well maintained place. Would definitely stay again. Only downside is limited parking but that’s everywhere in Keywest.
Zachary L.
Stayed 7 nights in Jun 2025
10/10 Excellent
Daniel A.
Feb 17, 2025
Liked: Cleanliness
Key West Charming
Great location. Quiet area but close to everything.
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
10/10 Excellent
Amy B., Louisville, KY
Mar 18, 2022
Liked: Cleanliness
Perfect location!!
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
10/10 Excellent
Andrew W.
Feb 6, 2022
Liked: Cleanliness
Southernmost Regatta
We had an amazing time. It was located perfectly. Super convenient and beautiful. Looking forward to coming back!
Andrew W.
Stayed 7 nights in Jan 2022
6/10 Okay
Emma C.
Jan 5, 2022
Liked: Cleanliness
Christmas Getaway
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
Emma C.
Stayed 8 nights in Dec 2021
2/10 Terrible
Rose Ann Z.
Nov 16, 2021
Liked: Cleanliness
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.
Rose Ann Z.
Stayed 7 nights in Nov 2021
10/10 Excellent
Ashley J.
Nov 5, 2021
Liked: Cleanliness
Great location
We loved the place. Our favorite part was the beautiful back patio. It was close to everything.
Ashley J.
Stayed 7 nights in Oct 2021
8/10 Good
Robert H.
Jan 16, 2020
First-time visitor to Key West
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
8/10 Good
Carrie K.
Apr 1, 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!
Carrie K.
Stayed 7 nights in Mar 2018
8/10 Good
Curt W.
Mar 20, 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.
Curt W.
Stayed 7 nights in Feb 2018
10/10 Excellent
Wayne B.
Nov 29, 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.