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Upscale end unit home @ Truman Annex close to Duval St

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Beach - Upscale end unit home @ Truman Annex close to Duval St (Key West)
Fridge, microwave, oven, stovetop - Upscale end unit home @ Truman Annex close to Duval St (Key West)
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A heated pool - Upscale end unit home @ Truman Annex close to Duval St (Key West)
Dining - Upscale end unit home @ Truman Annex close to Duval St (Key West)
Nestled in the tranquil Truman Annex community of Old Town Key West, this upscale home offers a serene escape. With its private entrance and contactless Check-In/Out, enjoy the peaceful tropical landscape and pool just 2 blocks from Duval St. Unwind with televisions in both bedrooms and living rooms, access to Shipyard Pool, high-speed internet access.

Reviews

10 out of 10
Exceptional

Entire condo

1 bedroom1 bathroomSleeps 3

Popular amenities

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

Add dates for prices

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

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool

Internet

  • Available in the condo: Internet access

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • Bedroom
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Wood stove

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Limited housekeeping
  • Phone

Location highlights

  • Near a hospital
  • Near the sea

Things to do

  • Bicycles
  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles

Similar properties

Courtyard
The Grand Guesthouse
Old Town Key West
  • Breakfast included
  • Parking included
  • Free Wi-Fi
  • Air-conditioning
9.6 out of 10, Exceptional, 1,000 reviews
The price is AU$233
includes taxes & fees
6 July - 7 July
The Grand Guesthouse
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
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
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

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
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

About the area

Located by the sea, this condo is in Old Town Key West, a neighbourhood in Key West. Southernmost Point 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. Jet skiing, scuba diving and snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby. Visit our Key West travel guide
View more Condo rentals in Key West
Map
Key West, FL

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    6 min walk - 0.5 km
  • A brick corridor with arched ceilings and benches.
    Fort Zachary Taylor Historic State Park
    8 min walk - 0.7 km
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    9 min walk - 0.8 km
  • A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.
    Mallory Square
    12 min walk - 1.1 km
  • Florida Keys National Marine Sanctuary
    5 min walk - 0.4 km

Getting around

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

Restaurants

  • Green Parrot Bar
    4 min walk
  • Margaritaville
    7 min walk
  • Blue Heaven
    9 min walk
  • Mangoes Restaurant
    7 min walk
  • Rams Head Southernmost
    7 min walk

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Upscale end unit home @ Truman Annex close to Duval St Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers 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.
More informationOpens 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

Cleanliness

10

Location

10

Staff & service

8.8

Property conditions & facilities

Reviews

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

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

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
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

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

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

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

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

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

Jen H.

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

Great choice for 2 people

Southard Breezes was very nice for me and my husband. The deck was large and had both shade and sun so it was convenient to have coffee or an afternoon cocktail. Bed and pillows were comfortable. The washer and dryer were a little loud but we would do the laundry when we were not in the bedroom! Having laundry available was a plus, though! Truman Annex is close to everything but just far enough away! Thanks for the great week!
Stayed 7 nights in Nov 2024
From a partner site

10/10 Excellent

Key West Trip

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 was our second stay at Southard Breezes. We love the location. We are two blocks from Duvall Street and a short bike ride to Truman waterfront park and Zachary Taylor State Park. The sunsets at Truman Waterfront Park are beautiful. We also seen a pod of Manatees. You are a short bike ride to all the restaurants and bars. Tracy was very responsive to any questions we had. Southard Breezes was as described very nice and clean. We will definitely be back to Southard Breezes again.
Verified

10/10 Excellent

Teresa C.

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

Cozy Condo

This cozy condo is ideally located and is great for two people. The area is generally safe and quieter than two blocks away on Duval. Fort Zach Beach and restaurants are only minutes away. Upon arrival, the house was immaculate, and contactless check-in was easy. The house has quality finishes and is well-appointed. Two bicycles and Tommy Bahama beach chairs are available, which is a nice touch. The queen bed was comfy. There are wood blinds on the bedroom window but no blackout curtains, so I will bring an eye mask if we go again. Having the washer/dryer available is convenient, and starter amounts of products are provided. The partially covered balcony expands the living space and was a nice spot on a rainy morning. There is a designated parking space, but we did not use it. We would stay there again if it were a couple's trip.
Stayed 7 nights in Nov 2024
From a partner site

10/10 Excellent

Maureen C.

Perfect location and great accommodations

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: Enjoyed every minute of our stay. The condo was very clean and homey. Plenty of space and everything you will need to enjoy your vacation. The location can’t be beat. Easily walkable to everything. If Key West is your destination, this is your location. Highly recommended!
Stayed 7 nights in Oct 2024
From a partner site

10/10 Excellent

Jennifer V.

Cozy Vacation Home

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 absolutely love this condo and the beautiful property. Location is perfect for walking everywhere .This is our 3rd time renting from Tracy and we again on our next trip to Key West, Our Happy Place.
From a partner site

10/10 Excellent

charles b.

nice week in the 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: A cute condo in Truman Annex that was perfect for 2. The bikes were in very good condition. The pool was refreshing and the location was great. Very clean condo with everything you would need. I would stay here again.
Stayed 7 nights in Aug 2024
From a partner site

10/10 Excellent

Skip W.

Birthday Week Shipyard Condo

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: Spent a week at the Condo to celebrate my birthday. Condo was beautiful, clean, and so close to everything we walked everyday. Would definitely stay here again. Everything was provided even detergent to wash your clothes. Only suggestion, a broom or vacuum to keep the floors clean.
Stayed 7 nights in Jun 2024
From a partner site

10/10 Excellent

Christy T.

Definitely Recommend

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 was a great property. The layout was very nice with a larger bathroom than most Shipyard condos. Everything was clean and it had all the supplies we needed. I would definitely recommend this condo! Also renting from Tracy is always a good experience!
From a partner site

10/10 Excellent

Kathleen F.

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: I have nothing but positive things to say! The rental was clean, in a nice location, and comfortable. I would definitely recommend it to anyone and I would stay here again!
From a partner site

10/10 Excellent

KARIN W.

Great location and condo

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 loved our stay here and found the location was perfect as we were able to walk everywhere. The condo was clean and well stocked and had everything we needed. We used the coffee pot daily and enjoyed sitting on the deck in the morning. We appreciated the beach chairs, cooler, and beach towels. We never did get around to using the bikes, but would have been great I'm sure! We found the bed a little uncomfortable (compared to ours's at home) and wish there were more pillows. We had an issue with the air conditioner (it was super hot during our stay) and reached out to Tracy who communicated back immediately and had a service company there in an hour! She was great to work with and we would definitely recommend staying here.
Stayed 7 nights in Aug 2023
From a partner site

10/10 Excellent

Thomas G.

What a Week

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 thoroughly enjoyed our stay at the Key West Condos Truman Annex. The condo was clean, well appointed and in a great location. Only had a couple of questions and the Owner answered promptly and patiently. Definitely would stay there again!
Stayed 7 nights in Sep 2023
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

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

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