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SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool!

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Welcome to Southard Sunset!
Cozy Porch
Relax on the porch
Step into your tropical abode
Open space

Reviews

9.6 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 463.2 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Dining area

About this property

SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool!

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.

COMFORT AND VALUE IN TRUMAN ANNEX…
This two bedroom first floor condominium is located in The Shipyard, a neighborhood of the coveted Truman Annex in the heart of Old Town Key West! Enjoy this comfortable ground floor front porch to sit and take in the passersby in true Key West fashion while you sip your coffee or relax with a glass of wine. With a preferred location and in exceptional condition, this little gem has a remodeled kitchen and bathroom and is located on the ground floor for your convenience. Throw your cares to the wind as you unwind in this charming, tree-shrouded neighborhood with walking paths and lanes. You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! The Shipyard also offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun.
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS AND AMENITIES...
Comfort and functionality greet you as you enter this delightful abode. The fully equipped kitchen has everything you need to create a delicious meal for your loved ones, with a full size refrigerator, dishwasher, microwave, oven/stove and mini island. Gather around the dining table for 4 and then curl up on the couch in the adjacent living area to watch your favorite shows and movies.

SLEEPING ARRANGEMENTS…
Unwind from your day of island fun in one of the two comfy bedrooms. There is a twin bedroom that can be converted to a king if desired and a second room with a queen bed. Both rooms offer a clothing dresser, small flat screen tv and storage/hanging closets. Enjoy a shared hallway bathroom with a large glass-door shower and a washer/dryer closet adjacent to it.

OUTDOOR LIVING…
Open the French door to the fenced private patio, inviting sultry breezes and Key West sunshine inside. This wonderful extension to the living space has a table for four where you can have your morning coffee or enjoy a cocktail after a long day of exploring. Fire up the grill and cook your fresh catch of the day!

PARKING...
This home does offer parking for one vehicle (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community.

PETS...
This is not a pet friendly home.

MULTI MONTH RESERVATIONS...
For monthly reservations, the following fees will be added PER MONTH:
Mid-stay clean
Pet fee (if applicable)

BOOKING DATES...
This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.

CONCIERGE SERVICES...
Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

CANCELLATION...
Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

COME STAY A WHILE...

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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  • Kitchen
  • Washing machine
  • Dryer
9.4 out of 10, Exceptional, (92 reviews)
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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
Property Registration Number 25230-130645

About the area

Key West

Located by the sea, this condo is in Old Town Key West, a neighbourhood in Key West. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum 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. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
Map
Key West, FL

What's nearby

  • Duval Street - 5 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Ernest Hemingway Home and Museum - 7 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 9 min walk - 0.8 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 14 min drive

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Margaritaville - ‬7 min walk
  • ‪Willie T's - ‬6 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk

Frequently asked questions

Is SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool! pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool!?

As of 30 Mar 2026, prices found for a 1-night stay for 2 adults at SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool! on 7 June 2026 start from AU$294, 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.

How much is parking at SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool!?

On-site parking is available at the property.

What time is check-in at SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool!?

Check-in begins at 4:00 PM.

What time is check-out at SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool!?

Checkout is at 10:00 AM.

Where is SOUTHARD SUNSET ~ 2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool! located?

Located in Old Town Key West, this condo building is within a 10-minute walk of Truman Waterfront Park, Duval Street and Fort Zachary Taylor Historic State Park. Ernest Hemingway Home and Museum and Florida Keys Beaches are also within 15 minutes.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 30 out of 36 reviews
Rating 8 - Good. 3 out of 36 reviews
Rating 6 - Okay. 3 out of 36 reviews
Rating 4 - Poor. 0 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

9.2/10

Cleanliness

9.6/10

Check-in

9.4/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jennifer W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, wonderful location and people in the community.
Stayed 28 nights in Feb 2026
Verified

6/10 Okay

Sara R.

Liked: Check-in, communication, location
The location was amazing. I felt a little more care could be taken in the condo. There were quite a few bugs, back patio was a mess and just overall in need of interior repairs and deep cleaning.
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Robin C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Key west walkable

Great stay in walking distance to all attractions
Stayed 7 nights in Nov 2024
From a partner site

10/10 Excellent

Larry G.

Perfect spot for a Key West getaway?

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: Lovely two bedroom unit, exceptionally clean and well provisioned, nice outdoor real patio, and so convenient to anything one wants to do in Key West. Host was very accommodating and communicative regarding anything we asked. Favorite spots: Butterfly and Nature Conservatory, Fort Zachary Taylor Beach, Truman Park, Fritta’s Cuban Burgers, Moondog Cafe, Frenchies Cafe, Higgs Beach.
Verified

10/10 Excellent

Dennis C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location to walk downtown and yet quiet in our area. So restaurants and shops nearby. Location was clean and maintained nicely. Directions for arrival and departure clear. Host responded quickly to any questions. We bought beach chairs to go to fort Jefferson every day. We left them in the closet of the twin beds.
Stayed 14 nights in Oct 2025
Verified

8/10 Good

Mark T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Enjoyed our stay

Excellent location. Clean. Property needs some updating and repairs
Stayed 7 nights in Mar 2023
Verified

10/10 Excellent

Yiseni S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Mini lobster season

We needed a last minute room for additional family members to join us for mini lobster season - this was quick and easy process with everything you need for key west stay. Family enjoyed there stay.
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Kathleen M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Prefect Location

The property was well maintained and exceeded our expectations. We enjoyed the outdoor patio. The location was prefect - close to Duval Street and Mallory Square. I would definitely recommend the condo.
Stayed 7 nights in Oct 2023
Verified

10/10 Excellent

Andrea K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Location

The location was great. Unit was exactly as advertised. A map of where to park and where the unit was located prior to arrival would have been amazing but Representative Via Text helped a little.
Stayed 7 nights in Dec 2024
From a partner site

10/10 Excellent

David L.

Key West Vacation

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than 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 and perfect location
Verified

10/10 Excellent

Amanda W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great space and location

Property was very comfortable and in a great location. We enjoyed the pool and surrounding area. Will definitely visit again! Property was clean and very accommodating. One suggestion would be a small vanity area for dressing/ makeup. We stay in Truman Annex often and this is one thing that would be such a nice addition, it we rarely find.
Stayed 7 nights in Jul 2024
From a partner site

10/10 Excellent

Diane R.

Key west

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: Great location
Stayed 7 nights in Feb 2023
From a partner site

10/10 Excellent

Linda B.

Just Off Duval October Review

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: We've stayed at this condo before. Great location and well maintained. Would recommend to anyone looking for a vacation rental in this area.
From a partner site

8/10 Good

Theresa R.

Nice rental

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: Great for a family rental.
Verified

10/10 Excellent

Jane B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Southard Sunset

The property is very nice. the location is perfect to Duval and Front Street. My only complaint is 4 adults with one bathroom is sometimes difficult and there wasn't an oven.
Stayed 14 nights in Mar 2023
From a partner site

10/10 Excellent

Randy S.

Great Property

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: We were so pleased with the location. Property was perfect for my family of four.
Stayed 7 nights in Dec 2023
From a partner site

10/10 Excellent

Chris A.

Great Stay

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: We were very pleased with our stay. The house was in great shape, well equipped and the Truman annex is an excellent location on Key West. The check-in and check-out process was very smooth.
From a partner site

10/10 Excellent

William S.

A hidden treasure in the Shipyard Condominiums at 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: As advertised. No surprises. Great location. Beautiful gardens throughout the community and backyard. If you’re looking for a comfy and perfect location for short term or long term stay then this is your place. Very smooth communication with Team Zintmaster. You’ll quickly understand why they’re the best in Key West!
Verified

10/10 Excellent

John R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vacation 2024

This property was in a quiet neighborhood near everything . We sat outside every morning having our coffee in a beautiful setting in back yard. In the evening we sat on front porch with a glass of wine. We will be back to Truman Annex !!
Stayed 10 nights in Apr 2024
From a partner site

10/10 Excellent

Carsten K.

Key West Perfect

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: One of the very best places we have ever stayed. Great location, clean and sooo comfortable. The management staff (Whitney) made it perfect. Thank you.
From a partner site

10/10 Excellent

Bonnie B.

Great vacation!

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: Great location! Quiet but can walk to restaurants, museums, and beach. Condo very clean and in excellent condition. Beach towels and 2 beach chairs were provided along with a fishing pole. The property management was very responsive to any questions.
From a partner site

10/10 Excellent

Leslie B.

Great 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: We just spent a week in Key West and had a very good experience. The condo was just as pictured. It was clean when we arrived. The best part is the location. We walked to Duval St daily and didn’t have to worry about finding parking. Lots of restaurants nearby.
Stayed 7 nights in Jul 2023
From a partner site

8/10 Good

A guest from SCHUYLKILL HAVEN, PA

Nice location close to Duval and Mallory Square.

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: The property description is accurate, it is close to Duval and Mallory Sts. The location had broken tiles covered by a rug in the bedroom. The landscaping outside could use some clean up and maintenance in the back yard.
Verified

10/10 Excellent

michael i.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Can"t get much better

My wife and I stayed at this wonderful condo 2/23. The location could not be better, Truman Annex is in the middle of everything worth experiencing in Key West. Easy walking distance to Truman White House, Duval Street is 1 block away but the condo is located in a quiet neighborhood, Fort Zackary is a short walk away. And of course many of the wonderful restraurants are a short walk .The check in process was seamless. Condo manager keep me posted as to when the condo was available, and was always available for any questions we had. Overall a wonderful condo, wonderful vacation.
Stayed 7 nights in Feb 2023
From a partner site

10/10 Excellent

Rebecca S.

Love Key West

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: Great condo in Truman Annex. Very clean and comfortable. Easy walk to downtown/ restaurants or rent a bike and explore! There is so much to see! Property manager provided seamless check in and was readily available should a question arise. Enjoyed our stay. Thank you.

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