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.
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.
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The room configuration is as follows:
Primary Bedroom / Queen bed Bedroom 2 / Two twin beds
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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.
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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
About the area
Key West
Located near the beach, 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. USCGC Ingham Maritime Museum and Florida Keys Eco - Discovery Center are also worth visiting.
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.) - 15 min drive
Restaurants
Green Parrot Bar - 4 min walk
Blue Heaven - 8 min walk
Mangoes Restaurant - 7 min walk
Moondog Cafe & Bakery - 8 min walk
Rams Head Southernmost - 7 min walk
Frequently asked questions
Does Communal Pool | Gated Community | Month-Long Stays | Key West Charming have a pool?
Yes, this property has a pool.
How much does it cost to stay at Communal Pool | Gated Community | Month-Long Stays | Key West Charming?
As of 12 May, 2026, prices found for a 1-night stay for 2 adults at Communal Pool | Gated Community | Month-Long Stays | Key West Charming on 5 Jul, 2026 start from S$242, 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 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.
Reviews
9.0
Wonderful
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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
Response from VrboOwner on 3 Jul, 2025
Thanks, Zachary! We're glad you enjoyed the cleanliness and upkeep of the place. Appreciate you noting the parking—a common challenge in Key West. We'd love to host you again!
Great location. Quiet area but close to everything.
Daniel A.
Stayed 7 nights in Feb 2025
Response from VrboOwner on 17 Feb, 2025
Thank you, Daniel! We're so glad you enjoyed the charming location and the peaceful yet convenient setting of Key West. We’d love to host you again in the future!
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.
Response from VrboOwner on 19 Sept, 2022
Thank you for sharing, Cliff! We would be thrilled to host you again soon. Please reach out if you need any assistance planning your next stay!
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
Response from VrboOwner on 19 Sept, 2022
Thank you for the kind words! We’re so happy your stay surpassed your expectations. Would you mind sharing with your family and friends who are due for a vacay? We’d love to continue providing a great experience to awesome customers like you. Thanks again!
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
Response from VrboOwner on 19 Sept, 2022
Thank you for your kind words!
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.
Response from VrboOwner on 21 Sept, 2022
Thank you for sharing! We would be thrilled to host you again soon. Please reach out if you need any assistance planning your next stay!
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.
Response from VrboOwner on 27 Sept, 2022
Thank you for sharing such a lovely review, Lisa! Here at AvantStay, we strive to ensure our guests have an amazing experience!
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
Response from VrboOwner on 19 Sept, 2022
We’re so excited to hear that you enjoyed your stay! Please reach out if you need any assistance planning your next vacation. We'd love to host you and your group again soon!
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
Response from VrboOwner on 21 Apr, 2025
Thank you, Wayne. We're happy to hear you enjoyed the convenient location and the quiet, clean space. Glad we could quickly take care of the washing machine issue, especially during a busy time like Fantasy Fest. Appreciate you staying with us and hope to welcome you again!
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.
Response from VrboOwner on 23 Sept, 2022
Thank you for your thoughtful review, Jennifer! Please reach out if you need any assistance planning your next vacation. We'd love to continue providing a great experience to awesome guests like you here at AvantStay!
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.
Response from VrboOwner on 19 Sept, 2022
Thank you so much for taking the time to review, Stephen! Your feedback is greatly appreciated. We'd love to host you and your group again soon!
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.
Curt W.
Stayed 7 nights in Feb 2018
Response from VrboOwner on 18 Mar, 2020
Curt, Thank you for taking the time and writing this review about Key West Charming. This is a great 2 bedroom rental, located in one of the most popular complexes in Key West - Truman Annex, only steps to Duval Street and short bike ride to Fort Zachary Taylor Beach.
We apologize the property did not meet your needs 100% but please give us a call next time when planning your trip to Key West, we will be happy to assist you again in finding the perfect rental for you. Thank you again.
At Home In Key West
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
Response from VrboOwner on 15 May, 2022
Amy,
Thank you for reviewing Key West Charming, one of our rentals in Truman Annex
At Home In Key West team
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!
Diane T.
Stayed 7 nights in Feb 2022
Response from VrboOwner on 21 May, 2022
Diane,
Thank you for leaving a review
We hope to see you again soon!
At Home In Key West team
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
Response from VrboOwner on 3 Apr, 2020
Robert,
Thank you for leaving a review
At Home in Key West team
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!
Carrie K.
Stayed 7 nights in Mar 2018
About the host
Hosted by AvantStay
At AvantStay, we pride ourselves on our guest experience. We do the trip planning - so you can spend more time on vacation. With 24/7 customer support, a dedicated concierge, and tech-enabled touchpoints from the moment you book to an easy and seamless check-out, we make your experience as carefree as you could possibly want it to be. AvantStay features 500 homes in 30+ destinations and is growing quickly. For any questions about your next trip, please don't hesitate to reach out directly and we'd be more than happy to help your vacation come true.
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They consistently provide great experiences for their guests