A Siesta Bay by AvantStay | Key West Walkable | Gated Community, Shared Pool | House in Key West

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.*
Here is your perfect opportunity to stay in one of the most popular complexes of Key West, the Truman Annex!
This beautiful two-bedroom one-bath second-floor condo rental just steps away from the shared pool and within walking distance of anything you'd want to do in Key West. Bright, airy, and with plenty of charm, Siesta Bay provides all the comforts you are looking for in a home away from home.
This property is the perfect combination of a quiet retreat and the best location for walking and biking throughout the entire island. All on one level the condo features a recently updated kitchen that is fully equipped with everything you need to prepare meals and a dinette with seating for 4 to enjoy dinner.
The inviting living room has glass doors that open to a wonderful balcony where you can unwind after a long day of sightseeing, sip a margarita and watch the breezes blow through the lush tropical landscaping. The master bedroom has a comfy queen size bed and the second bedroom has two twin beds. A full bathroom sits in the hallway between the two bedrooms just outside of each door for easy access.
When you are ready to cool down, the shared pool offers a perfect escape to take a dip in crystal clear waters, lounge poolside, and soak up some sun or read a book in the shade. And when you are ready to venture out you will find yourself only a hop skip and a jump from Duval Street, Mallory Square, and Fort Zachary Taylor State Park - to enjoy the bounty of restaurants, exciting nightlife, and beautiful beaches.
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!
AvantStay provides an upscale experience with services that elevate your stay and save time so you can enjoy every moment. Guests have access to a 24/7 support team. Whether it’s fridge stocking or in-home massages, AvantStay offers a variety of upgrades & experiences to enhance your stay.
*Home Truths:*
- This home has access to a shared pool and is part of a gated community.
- 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.
- 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.
- Please note that the twins at the property can not be converted into a king.
- 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.
- 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. All bookings over 30 days require a security deposit.
We report and prosecute all Credit Card Fraud.

A Siesta Bay by AvantStay | Key West Walkable | Gated Community, Shared Pool is located in Truman Annex. A Siesta Bay by AvantStay | Key West Walkable | Gated Community, Shared Pool provides accommodation, featuring Air Conditioner, Pool, TV, among other amenities. This House features Air Conditioner, Pool, TV, to make your stay a comfortable one.

A Siesta Bay by AvantStay | Key West Walkable | Gated Community, Shared Pool has 2 Bedrooms , 1 Bathroom, and max occupancy of 4 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Truman Annex has interesting places to visit. If you want to learn more about the House in Truman Annex, such as places to visit and things to do nearby, you can check below to learn more.