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


Bedrooms 2
Space 700 sq. ft.
Property type condo
Minimum Stay 1 - 3 nights


About the property

The Jewel of Shipyard Annex in Truman Annex

We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'.

This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plasma TV loaded with thousands of movies at your fingertips. Relax on the designer furniture while enjoying the full collection of Hemingway's books or lose yourself in The Master Bedroom retreat which has been luxuriously decorated with 1000 thread count bedding on the Romantic Canopy Bed with French doors leading out to a spacious rear patio overlooking the pool.

The guest bedroom has two twin upgraded pillow top beds that can be converted to a King bed to accommodate a family or two couples. The King is stocked with a very thick down padding and luscious linens for maximum comfort. Enjoy the sounds of the keys or music of Buffet as the guest bedroom is decorated in tribute to crooner and the island lifestyle detailed in framed sheet music.

If staying in for the evening or fixing breakfast or lunch have fun in the 1950’s themed state of the art kitchen equipped with an imported European SMEG Fridge and Stainless Appliances. Likewise, the bathroom has been decorated in an art deco style typical of an earlier time in the Keys.

The front Family room area has features a queen sleeper sofa bed with a down pad and bedding for extra sleeping space. All pillows and bedding are down and of high quality in order to provide maximum comfort on your stay. Quite simply, we designed this home to fit in with the Keys lifestyle. It is bright, open and lends itself to a vibe which we hope catapults you to a great stay in our beloved Keys.

Please enjoy the slide show of our new wonderful home in Key West and we hope to accommodate your vacation needs.


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More Details

Property Manager
Jenny Blaylock
Member since: 2010
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
March 16, 2018

About Jenny Blaylock

This home is managed by Simplicity Vacation Property Management. The home is owned by a family that loves to vacation in warm spots and has enjoyed Key West for many years. They loved the VRBO approach, but strive to offer a personable experience to our guests. In furtherance of this belief, they took great strides to decorate the home in such a way as to make it part of the total vacation experience. They hope when looking back on your vacation, the house will feature prominently in your memories and live on in spirit.

Jenny Blaylock purchased this condo in 2013

Why Jenny Blaylock chose Old Town

This property is a smaller property, but is located in the nicest area of Key West. We believe you will find it has been decorated impeccably and is designed with vacationers in mind with the installation of items such as closet organizers to avoid crowding the rooms with unnecessary furniture. It is a clean and above all else fun place to stay as a family or as a couple's get away.

What makes this condo unique

Our unit has a parking spot right in front of the front door and the back of our unit overlooks the pool area which is a gorgeous view. When comparing units available we found this particular unit to have a superior location within Shipyard as several overlook a parking lot or are in view of other unit's yards.


Old Town Condo Accommodation and Amenities

Property Type:
  • condo
  • floor 2
  • Guests provide their own meals
Floor Area:
  • 700 sq. ft.
House Rules:
  • Check-in: 3:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 6
  • Children welcome ...
  • Non smoking only
Location Type:
  • Downtown ...
  • Waterfront ...
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet ...
  • Linens Provided
  • Living Room ...
  • Parking ...
  • Telephone
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher ...
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining Area
  • seating for 4 people
  • 1 Bathroom
  • Bathroom 1 - toilet , shower
  • very hip art deco black and white styled bath with new shower enclosure over the tub. Spacious mirrored medicine cabinet and vanity offer space for all your toiletries.
  • 2 Bedrooms, Sleeps 6
  • Master Bedroom is beautifully furnished with Brand New Designer Canopy Bed and Mirrored side table with top of the line down bedding and 1000 thread count linens.
  • Books ...
  • Music Library ...
  • Satellite / Cable
  • Television ...
  • Video Library ...
  • Balcony
  • Deck / Patio
  • Lawn / Garden ...
  • Long-term Renters Welcome
  • wheelchair inaccessible ...
Pool / Spa:
  • Communal Pool ...
  • Heated Pool
  • botanical garden
  • churches
  • cinemas
  • health/beauty spa
  • marina
  • museums
  • playground
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • paddle boating
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • jet skiing
  • kayaking
  • parasailing
  • pier fishing
  • roller blading
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • swimming
  • water tubing
  • wind-surfing


Excellent! 4.7/5 -
(26 traveler reviews)

73% Complete
23% Complete
3% Complete
0% Complete
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average rating of 4.6923075 based on 26 reviews

Absolutely Adorable!

  • 5 of 5

We really enjoyed staying here. It is absolutely perfect location wise, easy walk to both ends of Duval. It is also so close to our favorite restaurant, Blue Heaven! Plenty of room for the two of us, comfortable beds, cute little kitchen...It was nice to not HAVE to eat out every night and we love the decor. We enjoyed the balconies, although would have liked somewhere to sit on the front balcony. We only have a couple minor recommendations, it would be nice to have a couple table lamps in the living room as the overhead lighting was a little too much sometimes and another small table or shelf on other side of the bed for glasses and phone. The walls are a little thin, we could hear our neighbors, especially their TV at night and we knew who was taking a shower when. 😉? That said none of this would keep us from coming back again. Thank you for a lovely week.

  • Submitted: Jan 22, 2018
  • Stayed: January 2018
  • Source: VRBO, from HomeAway
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Great location

  • 5 of 5

Clean, nice and a great area.

  • Submitted: Jan 1, 2018
  • Stayed: December 2017
  • Source: HomeAway
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Very cute and convenient rental

  • 5 of 5

We had a great time staying over the weekend for a wedding trip. The rental is really conveniently located just a little way back from Duval St so you can quickly get to the night life but it's nice and quiet when you want to get some rest. Everything was well maintained, clean, and comfortable. We also really enjoyed the decor!

  • Submitted: Dec 10, 2017
  • Stayed: December 2017
  • Source: HomeAway
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Pittsburgh, PA

Overall, just perfect!

  • 5 of 5

My husband and I come to Key West a couple of times a year and decided to try renting a condo for the first time. This one was perfect! Neat and clean, had some kitchen basics (salt, pepper, coffee filters, etc.), close to the pool and central location in Old Town. A quick grocery shopping trip saved is lots of money as an alternative to eating out every meal.

I have to give a shoutout to Jenny, the property manager that I worked with to book the place. We were supposed to come down the week of Irma. She was very responsive and helpful in getting our reservation adjusted to another week. What could have been an expensive lost trip turned out perfectly, and Jenny has a lot to do with that, THANK YOU!! Will certainly make an effort to work with her company again.

  • Submitted: Dec 5, 2017
  • Stayed: November 2017
  • Source: HomeAway
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Cozy and Unique

  • 4 of 5

The condo was beautiful overall. It is close to everything - but we knew that since we have rented in Truman Annex for 3 prior stays. The owners were right - def rent bikes for your duration of your stay. There are bike racks EVERYWHERE. We covered so much of the island on the bikes. One negative about the condo is that on our first night there we were startled awake at 2am with what sounded like King Kong banging on our front door! It was the downstairs renters, there smoke alarm went off and they wanted to make sure that nothing was burning in our unit because there alarm went off for no reason, we thought they were coo-coo. However, at 5 am that same morning we were awoken again by the screeching sound of our own smoke alarm, going off for no apparent reason. We thought that that was the end of that, however, on our last night there it went off again for no reason at 6 am, and then again at 6::15. There was not option of taking the batteries because it is hard wired, so this was incredibly stressful, irritating, and not a good way to start our day. Since it was Thanks giving week that we stayed there, we had bought a small turkey breast at a nearby grocer named Faustos (which the bikes with their baskets came in handy). We would suggest to the owner that it would have been nice to have at least one sauce pan (small pot) to cook vegetables in, we had to nuke them instead. There were plenty of fresh towels and the master bed was very comfortable. I would suggest that you wash you towels right after u use them because the washing machine does not hold much at all, so that's what we did and this way we wern't stuck with waiting of loads of laundry to finish on our last day, or worse yet, get charged for the 2 or more loads of laundry, which is in the contract.All in all, we had an amazing time and loved the condo and all the Hemingway memorilbilia. It is def tastefully decorated, we were pleasantly surprised! Oh, before we left I was reading previous reviews, and one complained about a "noisy" master bed, well, they mush have fixed that problem because it was very quiet during our stay. I would say that this condo is perfect for one couple, a little cramped for two couples I would imagine, but it was just my husband and myself so who knows, it may work for 2 couples. This is one Thanksgiving we won't forget, that's for sure!! Two thumbs up for this rental. We hope u enjoy it as much as we did! Marc & Anne Phillips

  • Submitted: Nov 26, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
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Girls getaway

  • 5 of 5

Excellent location. Clean. Well stocked. Would definitely stay again on my next visit to Key West!

  • Submitted: Nov 17, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
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Toast to the Sunset at Mallory Square which is a short walk from the Truman Annex.




Additional information about rental rates

Damage Waiver Fee $49 + Tax
Cleaning fee $125 + Tax
Tax Rate 12.5%

20% Premium for Holiday weeks


Manager'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.