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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

New Upscale Rental in Truman Annex!

Bedrooms 1
Space 580 sq ft
Property type condo
Minimum Stay 6 - 7 nights


About the property

Beautifully Remodeled -1BR/1BA End Unit Shipyard Condo in Truman Annex

Location, Beauty and Comfort! Southard Breezes has what you are looking for! 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 or 929455 Sunrise off Southard)


Our Condo includes the following:

- Bedroom with Queen Bed & Television

- Family room large television & queen sleeper sofa

- Bath/Shower combination in bathroom

- Fully equipped kitchen*

- 2 Bicycles for Guests to use during their stay

- Ft. Zachary Taylor Beach Pass

- Bed Linens, Bath & Beach Towels

- Hairdryer

- Beach Chairs

- Cooler

- Full size stacked washer & dryer

- Access to Truman Annex Pool

- Partially covered oversize deck

- Gated parking place in front of condo

- 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

* Kitchen- Full Kitchen Silverware, Dishes, Cooking Utensils Provided, Stove/Oven, Refrigerator, Microwave, Dishwasher, Coffee Maker & Blender

This is a sister property to Sunset on Southard (VRBO Listing #877318) & Sunrise off Southard (VRBO Listing #929455). Please see these properties for owner reviews and additional availability.

More Details

Tracy & Harold Dubensky
Member since: 2016
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
April 26, 2018

About Tracy & Harold Dubensky

We have been visiting Key West for more than a decade. Each time we returned, we fell more in love with the island. We finally decided we had to have a piece of this paradise! We have since added two more to our family of Key West homes!! See our other properties located in the Shipyard community of the Truman Annex. (Sunset on Southard #877318 & Sunrise off Southard #929455) We hope you enjoy the beautiful island and all it has to offer as much as we do.

Tracy & Harold Dubensky purchased this condo in 2017

Why Tracy & Harold Dubensky chose Old Town

This home has a unique layout which offers some benefits over other 1 BR homes in The Shipyard. It has a large open living area with an open kitchen/dining area. There are 2 sets of French doors opening to a large rear balcony making it feel larger and making the transition to the outdoors appear seamless. The ceiling in the living area has been raised to expose the beams which have been whitewashed along with the hardwood floors which you don't see often in Key West! Additionally, the bathroom is almost twice the size of most comparable homes with a 48" vanity and a large glass enclosed shower with beautiful tilework.


Old Town Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 2
Building Type:
  • building
  • Guests provide their own meals
Floor Area:
  • 580 sq ft
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 3
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets considered ...
  • Non smoking only
Location Type:
  • Near The Ocean
  • Air Conditioning
  • Clothes Dryer ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Telephone ...
  • Towels Provided ...
  • Washing Machine ...
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 4 people
  • 1 Bathroom
  • Bathroom 1 - toilet , shower
  • Large teak vanity and medicine cabinet. Beautiful tiled shower with multi spray dual showerhead
  • 1 Bedroom, Sleeps 3
  • Bedroom 1 - 1 queen
  • TV in Bedroom
  • Books
  • Satellite / Cable ...
  • Television ...
  • Balcony ...
  • Bicycles ...
  • 2 bicycles
Pool / Spa:
  • Communal Pool ...
  • Heated Pool
  • botanical garden
  • churches
  • cinemas
  • library
  • marina
  • museums
  • playground
  • restaurants
Leisure Activities:
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • paddle boating
  • photography
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • kayaking
  • parasailing
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • swimming
  • water tubing


5/5 -
(1 traveler review)

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New Upscale Rental in Truman Annex!
average rating of 5.0 based on 1 reviews

1st trip to KW! We will be back and, unless we bring a ton of people, will stay in this unit again!!

  • 5 of 5

It is very clear Tracy and Harold have spent quite a bit of time in Key West! They truly thought of everything when buying and putting together this unit... Location, location, location - you can walk anywhere you want to go with ease yet you can sit on the large deck in the sun or shade and enjoy peace and quiet. And if you want more range or get where you are going a little quicker they provide bikes that are easily accessible on the property - biking was a whole lot easier and cheaper than driving a car but if you do have a car they provide a parking space. They provide a park pass for two to what we felt was the best beach on Key West along with everything you would need to enjoy it - perfect Tommy Bahama chairs, terrific beach towels and cooler. I concede we drove here even though it was pretty close just because it was really easy to put everything in the car and drive the 3 or 4 minutes over.

You can also tell Tracy and Harold had a lot of fun with the remodel and decorating of this property. The décor is perfect for the location and the space has been used incredibly to make the unit function quite well - we especially liked the double French doors out to that great deck.

We enjoyed the fully appointed kitchen but mostly to reheat leftovers from all the incredible meals we ate out. We tried many of the restaurants Tracy and Harold recommended and were not disappointed - we even went to Santiago's twice... We also enjoyed the excursions with the recommended companies which also were incredible. We had a family of dolphins play beside our sail boat as we were returning from a snorkel/kayak trip. We were told by Janet - our captain - that they were teaching their kid how to breath - pretty cool!

Believe them when they you to pack light! You could probably pack one change of clothes and a swim suit as they even have a washer and dryer fit into the unit.

This was our first trip to Key West. After booking everything pretty last minute we had several folks tell us of negative things they had heard about it. All I can say is we are really glad everything was already booked, with the guidance Tracy and Harold provided in their confirmation package we had a tremendous time. There are definitely a lot of people, especially at certain times of the day. It seems like you can make your visit as wild or tame as you want.

We will be back and if it is just the two of us we would love to stay here again. Thanks Tracy and Harold!!!

  • Submitted: Mar 31, 2018
  • Stayed: March 2018
  • Source: VRBO, from HomeAway
Owner's Response: Thank you so much for the wonderful review! We truly appreciate having you as our guest and are so glad to hear you enjoyed your stay and that our Traveler's Guide was helpful. We hope you will return to us again in the future!
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Nearest Airport
4 Miles
Key West Airport (EYW)
Nearest Barpub
0.25 Miles
Green Parrot
Nearest Golf
5.7 Miles
Key West Golf Club
Nearest Restaurant
0.25 Miles
Charlie Mac's
Nearest Beach
0.25 Miles
Ft Zachary Taylor State Park
Car: not necessary


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $300
Pet Fee $100 + Tax
Tax Rate 12.5%

-Please call for Monthly Rental Rates as we will discount for monthly stays.
-Reservations are not final until required deposit has been paid and rental contract has been fully executed by Guest & Owner.
-$50 cancellation fee applies to any finalized reservation.
-Certain special events may not be included in disclosed rates until dates are known.
-Pets are permitted at owner's discretion with monthly rentals only.
-Guest and all occupants must be 25 years of age or older. No occupants under the age of 25 are allowed unless accompanied by a parent or other legal guardian.

Owner's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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