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Upscale end unit home @ Truman Annex close to Duval St

Photo gallery for Upscale end unit home @ Truman Annex close to Duval St

Ft. Zachary Taylor Beach
Front Entrance - Feel the "southard breezes" as you approach this home....
Southard Breezes Front Entrance - Enter your own tropical paradise!
Front Porch
Front View

Reviews

10 out of 10
Exceptional
1 bedroom1 bathroomSleeps 3

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Parking available

Explore the area

View map
Key West, FL
  • Place, Florida Keys National Marine Sanctuary
    ‪5 min walk‬
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪14 min drive‬

Rooms & beds

1 bedroom (sleeps 3)

Bedroom 1

1 Queen Bed

Other Space 1

1 Double Sofa Bed

1 bathroom

Bathroom 1

Shower only

Spaces

Kitchen
Balcony
Dining area

About this property

Upscale end unit home @ Truman Annex close to Duval St

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and paper products along with handsoap and toiletries. The home has a private entrance and contactless Check-In/Out.

Need to stay connected during your trip? We offer high speed cable internet.

This upscale home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval St. We are just outside the entrance to Ft Zachary Taylor State Park and Beach and so close to many of Key West’s popular attractions. After a full day of taking in many of the island's wonderful experiences, come back to all the comforts of home. This open airy home offers a fully furnished kitchen, eating area, living room and bedroom with a queen size bed and full bath. There are televisions in both the bedroom and living room along with wireless internet access. Two sets of French doors bring in lots of light and open to a large balcony where you can enjoy a meal or relax and sip umbrella drinks on the chaise lounges in your own private tropical paradise. Gated parking lot with one reserved space. (For reviews on our other homes, please see Listing # 877318 Sunset on Southard)

Amenities

- Televisions in bedroom and living area
- 2 Bicycles for Guests to use during their stay
- Bed Linens, Bath & Beach Towels
- Hairdryer
- Beach Chairs & Cooler
- Access to Shipyard Pool
- Partially covered oversize deck
- Reserved parking place
- Secure high speed wireless internet in condo
- Only a few short blocks from Duval Street and Mallory Square
- Short walk to the Fort Zachary Taylor State Park Beach
- Fully equipped Kitchen with Silestone counter and eat in bar- Silverware, Dishes, Cooking Utensils Provided, Stove/Oven, Refrigerator, Microwave, Dishwasher, Coffee Maker & Blender

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Sunset... - Now you know why we named the home "Sunset on Southard"
Unique Home with loft @ Truman Annex
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  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
9.8 out of 10, Exceptional, (119 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

About the area

Key West

Old Town Key West, a neighbourhood in Key West, is home to this condo. 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.
Map
Key West, FL

What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Duval Street - 6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Ernest Hemingway Home and Museum - 9 min walk - 0.8 km
  • Mallory Square - 12 min walk - 1.1 km

Getting around

  • Key West, FL (EYW-Key West Intl.) - 15 min drive

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Margaritaville - ‬7 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪La Concha Bar - ‬8 min walk

Frequently asked questions

Is Upscale end unit home @ Truman Annex close to Duval St pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Upscale end unit home @ Truman Annex close to Duval St?

As of 4 May 2026, prices found for a 1-night stay for 2 adults at Upscale end unit home @ Truman Annex close to Duval St on 4 September 2026 start from NZ$521, 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 Upscale end unit home @ Truman Annex close to Duval St?

On-site parking is available at the property.

What time is check-in at Upscale end unit home @ Truman Annex close to Duval St?

Check-in begins at 4:00 PM.

What time is check-out at Upscale end unit home @ Truman Annex close to Duval St?

Checkout is at 10:00 AM.

Where is Upscale end unit home @ Truman Annex close to Duval St 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. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 15 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 118 out of 125 reviews
Rating 8 - Good. 7 out of 125 reviews
Rating 6 - Okay. 0 out of 125 reviews
Rating 4 - Poor. 0 out of 125 reviews
Rating 2 - Terrible. 0 out of 125 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

8.8/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Melissa G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a great location and able to walk to everything you would want to see with ease! The home was spotless, cozy, and comfortable and would highly recommend!
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Kristyn S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and beautiful place.
The outside of our condo.
The living room
The view from our balcony.
Stayed 7 nights in Oct 2025
Verified

10/10 Excellent

Frank B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Room was very nice and newly renovated. Decor was beachy. Location was near everything. Host communicated well.
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Brian G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great condo! Was very clean and had everything we needed. The location could not be beat and communication with host was excellent.
Stayed 7 nights in Oct 2025
Verified

10/10 Excellent

Janet H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for our needs.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Michelle

Liked: Cleanliness, amenities, property conditions & facilities, communication
Nice unit, good location & well maintained
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Tim S.

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

Nice place, great location

Enjoyed our stay at the Truman Annex. Short walk to Duval street and the park and beach behind the annex are nice too. Would stay again - no complaints!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Michael L.

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

Southard Breeze

Loved our stay here, super clean, super convenient to walk everywhere and comes with 2 bikes if you dont want to walk. Very comfortable place to stay and would definitely stay here again
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

John M.

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

Great location in Key West

Great vacation in Key West at a great condo that worked very well for my wife and I. Location is close to everything in Old Town and having bikes was great as well !
Stayed 7 nights in May 2024
From a partner site

10/10 Excellent

Bernie S.

Can’t go wrong here!

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: This is a great spot, and a great space. Clean, well-appointed and in a great area. Close to everything, and quiet. The owners are extremely easy to work with and the balcony is just beautiful and relaxing. Rent here, you won’t be sorry!
Verified

10/10 Excellent

Sarah V.

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

Wonderful

Property was clean, great location, we enjoyed it thoroughly.
Stayed 7 nights in Jul 2022
Verified

8/10 Good

John M.

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

Shipyard 2nd floor condo. Great location

We had a nice 3 weeks, everything we needed was supplied except a step stool
Stayed 21 nights in Mar 2025
Verified

10/10 Excellent

Katie Todd F.

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

25th Anniversary Trip

Southward Breezes was perfect for our trip! Close in distance to everything we wanted to do on the west end of the island! Easy in and out and great access to pool and bikes. Definitely a place we would come back to!
Stayed 7 nights in Apr 2024
Verified

10/10 Excellent

Kathy J.

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

Perfect location

Great location-10 minute walk to Duval Street, Mallory Square, Fort Zachary Taylor park, southernmost point. Rental had everything we needed. Would definitely go back!
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Thomas C.

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

Awesome stay

Great location, very clean and updated. I would love to make this a regular stay. I have stayed in the same complex for years with friends, this time it was just my wife and I this condo was perfect.
Stayed 7 nights in Nov 2022
Verified

10/10 Excellent

June L.

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

Key West vacation

The condo was exactly like the photos. The porch was perfect for morning coffee!
Stayed 7 nights in Oct 2023
Verified

10/10 Excellent

Leslie R.

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

Key west vaca

Loved the condo. Close to everything. Really enjoyed having the bikes. Comfortable bed. We had a great week!
Stayed 7 nights in Sep 2024
Verified

10/10 Excellent

Michelle S.

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

November 25 2023

Enjoyed our stay & we'll be back! Property is amazing, condo clean & beautiful, location fantastic.
Stayed 7 nights in Nov 2023
Verified

10/10 Excellent

tammy e.

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

kids first trip to key west

We loved this property. Loved the deco and furnishings and it had all the conveniences of home. We would definitely rent this condo again!! loved the whole neighborhood and pool amenities and closeness to the beach also!!
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Verified traveller

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

Fantastic location, bonus to have use of bicycles

The condo is within walking distance to everything that we wanted; Beach, restaurants, and shops. The bikes were in great shape and we used them to get to the beach, just used the picnic tables there.
Stayed 7 nights in Oct 2023
Verified

10/10 Excellent

Tom and Valerie W.

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

Awesome unit and location

The unit was in a perfect location and was very nice. The entire unit has been updated with new appliances and furnishings. All the action on Duval St is close but not too close. And Ft. Zachary Taylor is in close walking distance or a short bike ride using the nice bikes that were supplied. We would definitely stay here again!
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Michelle Beaumont O.

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

Great week in Key West

The condo was adorable and within walking distance to all the fun places on Duval. Truman Annex neighborhood was very pretty and quiet, loved the pool to cool off. Great communication with Tracey. Thank you, we will be back!
Stayed 7 nights in Sep 2022
Verified

10/10 Excellent

Dawn W.

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

Perfect location

This condo is central to everything Key West. Bicycles made it super easy to get around, but everything is close enough to walk. Beautiful property. Easy access. Great communication with owners.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Angelene A.

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

Perfect 2🌟🌟🌟🌟

Everything you would ever need is in this condo. It's clean and well maintained. The deck is a beautiful area to have your morning coffee or just relax. The location is excellent. Within walking distance to many sights. Highly recommend and cannot wait to come back.
Stayed 7 nights in Oct 2021
Verified

10/10 Excellent

AMBI B.

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

Paradise!

We thoroughly enjoyed our stay. The condo was exactly as describe….beautifully decorated and stocked with everything you would need. The LOCATION was perfect! A huge plus was the bikes that were provided. We rode them everywhere and really enjoyed living the Key West lifestyle while we were there. If we ever return to Key West I will definitely book this property again!
Stayed 7 nights in Jun 2021

About the host

Hosted by Key West Property Services, LLC

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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