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

D & D's Paradise - Old Town Key West Truman Annex Shipyard Condo

Bedrooms 2
Space 660 sq. ft.
Property type condo
Minimum Stay 0 - 7 nights


About the property

Condo, 2 Bedrooms, 1 Bath, (Sleeps 4)

This two bedroom fully-furnished condominium is located in Truman Annex, a private and quiet gated community of Private homes and condominium complexes within two blocks of Duval Street, five blocks of Mallory Square, and walking distance to Fort Zachary Taylor State Park and Beach.

This is our second home, which has been renovated with a new kitchen, new bathroom vanity, cabinet and tile floor, carpeted stairs and bedrooms, window treatments, ceiling fans and fresh paint, as well as being redecorated with high quality furnishings. One bedroom has a queen bed and the other bedroom has two twin beds, both with luxury mattresses and bedding, and a 22” LCD TV. This second-floor condominium has a shaded front porch balcony and new Anderson French Doors off the living room that open to the sunny rear deck. The living room is comfortable and features a 40” LCD HDTV and Blu-ray player.

We hope you will enjoy our retreat and all that Key West has to offer.

Keywords: Shipyard Condo, 1 Level, 2nd Floor, 1 Open Back Deck, 1 Covered Front Balcony, 2 Bedrooms.

More Details

Member since: 2010
Speaks: english
Response time:
Within 2 days
Response rate:
Calendar last updated:
February 2, 2018

Why The Owner chose Old Town

We have vacationed in Key West since first coming in 1999, staying every time in a Truman Annex Shipyard Condo. We loved it so much that we decided to buy our second home here in late 2009 as we plan for retirement in the not to distant future (We hope!). The Shipyard Condominium is a well maintained, secure, and tranquil community yet it is located only two blocks from famous Duval Street with all of it's shopping, restaurants and nightlife, five blocks from Mallory Square with it's famous Sunset Celebration and a short walk or bike ride to Fort Zachary State Park & Beach.

What makes this condo unique

The front balcony is a great place to people watch while having a cup of coffee in the morning or a wine later in the day. And our sunny back deck offers privacy and lush greenery for a dinner with family or friends, or just to lounge and read a book.


Old Town Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 2
Building Type:
  • building
  • Guests provide their own meals
Floor Area:
  • 660 sq. ft.
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 4
  • Max. adults: 2
  • Min. age of primary renter: 25
  • Children welcome ...
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
Location Type:
  • Downtown ...
  • Air Conditioning ...
  • Broadband Access ...
  • Clothes Dryer ...
  • Hair Dryer
  • Heating
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Parking Off Street ...
  • Towels Provided ...
  • Washing Machine ...
  • Wireless Internet
  • Coffee Maker ...
  • Cooking Utensils
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 4 people
  • 1 Bathroom
  • Bathroom 1 - toilet , combination tub/shower
  • 2 Bedrooms, Sleeps 4
  • Bedroom 1 - 1 queen
    Bedroom 2 - 2 twin/ single
  • High quality furnishings, 22' LCD HDTV in both bedrooms, six (6) foot wide closet in Master (Queen) bedroom and four (4) foot wide in Twin bedroom.
  • DVD Player ...
  • Satellite / Cable ...
  • Television ...
  • Toys ...
  • Balcony ...
  • Deck / Patio ...
  • Outdoor Grill ...
  • Senior Adults Only Community
  • wheelchair inaccessible
Pool / Spa:
  • Communal Pool ...
  • Heated Pool
  • arboretum
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • restaurants
  • ruins
Leisure Activities:
  • antiquing
  • beachcombing
  • boating
  • eco tourism
  • photography
  • shelling
  • shopping
  • sight seeing
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • laundromat
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • jet skiing
  • kayaking
  • paragliding
  • parasailing
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • tennis
  • water skiing
  • wind-surfing


Exceptional! 5/5 -
(16 traveler reviews)

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D & D's Paradise - Old Town Key West Truman Annex Shipyard Condo
average rating of 5.0 based on 16 reviews

Perfect Get Away

  • 5 of 5

Great location, close to everything. My husband, two teenagers, and I rented bicycles and rode everywhere. Close to Mallory Square, Ft Zachary Beach. The condo community is very nice with friendly neighbors, very safe and secure.

The condo itself had everything we could think of. It is very clean and organized. It was nice to have the linens provided and laundry in the condo. We had a great family vacation!

  • Submitted: Mar 22, 2017
  • Stayed: February 2017
  • Source: HomeAway
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Westport, MA

A Great Place to Stay in Key West

  • 5 of 5

This was my first trip to Key West. This condo was fantastic. Was in impeccable condition on arrival. Full kitchen available to prepare meals, closest grocery store is only a few blocks away. The AC works great. Deck and balcony were perfect. The pool was amazing! Beach access was a bonus. As far as are right on the middle of everything! Walking distance to a lot of places, but bicycles worked the best! Bike rental shop is literally a few hundred feet down the street. Awesome condo, very clean and modern, great value, very easy dealing with the owners...highly recommend to anyone. Will definitely be returning.

  • Submitted: Jun 3, 2015
  • Stayed: May 2015
  • Source: VRBO, from HomeAway
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Huron, Ohio

Home Away From Home

  • 5 of 5

I have returned to this relaxing piece of heaven for several years and plan on doing so as long as I can because this propery is truly a home away from home. I echo what other reviews have noted: great location, well-equiped, exceptionally clean, decorated beautifully yet comfortable, etc. What makes this property stand head & shoulders above other choices in the Truman Annex is the owners. They have made every step of the rental process easy and hassle-free. More importantly, as owners they too call it their home away from home and use their wonderful condo when they have the opportunity. As with any home they take pride in their property and that care and love clearly is evident. . .and we who are fortunate to also enjoy this wonderful "paradise" are blessed. I'm eager for my 2016 stay.

  • Submitted: May 24, 2015
  • Stayed: January 2015
  • Source: VRBO, from HomeAway
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Dayton OH

Truman Annex Condo!

  • 5 of 5

We had a wonderful trip to Key West!!! The condo was perfect for our family! We found everything was nice and clean which made our stay even more comfortable. The Truman Annex is a lovely quiet community and walking distance to Fort Zachary Taylor Park and to the busy nightlife on Duval. We would highly recommend renting this unit and we're even planning for next year!!!

  • Submitted: Apr 21, 2015
  • Stayed: April 2015
  • Source: VRBO, from HomeAway
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Great Key West condo!

  • 5 of 5

This condo is awesome. In quiet Truman Annex, it's 3 blocks away from the action of Duvall St. and centrally located to all the sites in Key West. We traveled with our teen daughters and it was the perfect space for us. The back deck was nice for a quiet place to read and the front deck was great for people-watching. It's close to Fort Zachary Taylor State Park and the unit comes with a park pass--which was a great add-on. We had a great week and highly recommend this condo as home-base.

  • Submitted: Apr 13, 2015
  • Stayed: March 2015
  • Source: VRBO, from HomeAway
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Absolutely Perfect

  • 5 of 5

We had a great time, Location was perfect and the unit was well equipped. We had everything we needed plus some.

  • Submitted: Apr 13, 2015
  • Stayed: February 2015
  • Source: VRBO, from HomeAway
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Nearest Airport
4 Miles
Key West International Airport
Nearest Barpub
0.2 Miles
Green Parrot Bar
Nearest Ferry
1 Miles
City Bight Ferry Terminal (100 Grinnell St)
Nearest Golf
4.9 Miles
The Key West Golf Club, Rees Jones 18-hole Design
Nearest Motorway
0.2 Miles
Nearest Restaurant
0.3 Miles
La Trattoria Restaurant & Virgilio's Martini Bar
Nearest Beach
0.7 Miles
Fort Zachary State Park Beach
Car: not necessary

The condo is located within just a few blocks of Truman's Little White House, Mallory Square with it's famous Sunset Celebration, Hemmingway's House, Key West Lighthouse, and Fort Zachary Taylor State Park & Beach. We often visit Caroline's Cafe to enjoy their 'Famous Fish Sandwich' or 'Salad Deluxe', and it is a great place to people watch on Duval. We love 'Sound Check' at the Green Parrot Bar every Friday and 'The Bubba System Band' at Grunt's Bar on Saturday nights. The Blue Macaw Island Eats & Bar is a newly opened restaurant where we enjoy breakfast and making our own Bloody Mary.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $500
Cleaning Fee $120 + Tax
Tax Rate 12.5%

US Residents only. Rentals are in weekly increments, Sat-Sat. Minimum age limit for renters. This is a nonsmoking unit. Sorry, we cannot allow pets. Security Deposit may be higher for Holidays, Festivals and Special Events.

Once you provide us your booking information (Guests names, addresses, home & cell phone numbers) we email you a lease to sign and return within 2 business days. Once we receive your signed lease and payment then your booking is confirmed for the lease dates.

Check-in & check-out information, as well as other pertinent information, is emailed to you 2-3 days before check-in.

Owner's Cancellation Policy

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