See all properties
Condo

Hands-Down Best Deal in Key West!

Photo gallery for Hands-Down Best Deal in Key West!

Come and Experience 'The Writer's Retreat'
Shipyard Condominiums are located within the Guard Gated Truman Annex Property
Separate Guard Gate into the Shipyard condo area
Front of the home with very close parking available
Entering through the first floor door takes you up to the second floor unit

Reviews

9.4 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 6700 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space

Explore the area

View in a 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

2 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 King Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Garden
Dining area

About this property

Hands-Down Best Deal in Key West!

City of Key West Business License # 28224

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.

TO VIEW OUR OTHER PROPERTIES VISIT
VRBO Listing #412277 & #497962 for Catalina Island
VRBO Listing #316356 PGA WEST La Quinta
VRBO Listing #592709 for San Clemente Beach
VRBO Listing #633858 for Park City Utah
VRBO listing #724909 for Garden District New Orleans
VRBO listing ID 815366 For Kiawah Island, Charleston South Carolina
VRBO Listing ID 901935 for Newport Beach

Please see contract for additional details.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Air conditioning
Outdoor Space

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Welcome to your island home!
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!
Truman Annex
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
9.8 out of 10, Exceptional, (38 reviews)
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
default

Children

Children allowed: ages 0-17
Two twin beds or can be converted to King
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted
RENTAL AGREEMENT - A valid Driver's License and signed Short-Term Rental Agreement are due after booking confirmation.

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Key West

Located on the waterfront, this condo is in Old Town Key West, a neighborhood in Key West. Ernest Hemingway Home and Museum 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 Mel Fisher Maritime Museum are also worth visiting. Jet skiing, kayaking, and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Map
Key West, FL

What's nearby

  • Duval Street - 5 min walk - 0.4 km
  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Ernest Hemingway Home and Museum - 7 min walk - 0.7 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 9 min walk - 0.8 km

Getting around

  • Key West Intl. Airport (EYW) - 8 min drive

Restaurants

  • ‪Green Parrot Bar - ‬6 min walk
  • ‪Margaritaville - ‬6 min walk
  • ‪Blue Heaven - ‬10 min walk
  • ‪La Concha Bar - ‬6 min walk
  • ‪Jack Flats - ‬6 min walk

Frequently asked questions

Does Hands-Down Best Deal in Key West! have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Hands-Down Best Deal in Key West!?

As of Apr 18, 2026, prices found for a 1-night stay for 2 adults at Hands-Down Best Deal in Key West! on May 7, 2026 start from $160, 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.

Is Hands-Down Best Deal in Key West! pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Hands-Down Best Deal in Key West!?

Check-in begins at 3:00 PM.

What time is check-out at Hands-Down Best Deal in Key West!?

Check-out is at 10:00 AM.

Where is Hands-Down Best Deal in Key West! located?

Located in Old Town Key West, this condo building is within a 10-minute walk of Jackson Square and Duval Street. Florida Keys Beaches and Mallory Square are also within 15 minutes.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 149 out of 210 reviews
Rating 8 - Good. 45 out of 210 reviews
Rating 6 - Okay. 14 out of 210 reviews
Rating 4 - Poor. 1 out of 210 reviews
Rating 2 - Terrible. 1 out of 210 reviews

9.2/10

Cleanliness

2.0/10

Staff & service

4.8/10

Amenities

6.8/10

Property conditions & facilities

9.8/10

Check-in

9.6/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Carla H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Ideal location, walking distance to restaurants and main tourist attractions Lodging was very clean and comfortable, enjoyed the pool and quiet neighborhood. Would definitely stay again
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Vicki

Liked: Cleanliness, communication
wonderful place to stay
Stayed 2 nights in Mar 2025
Verified

8/10 Good

Sue M.

Liked: Cleanliness, location, listing accuracy
We enjoyed our stay. The condo is in a great location. There was neighbor noise, and the units are close. But, pretty comfortable.
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Cheryl A R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The condo was very clean. The location was close to beaches, bars, and restaurants. The Hostess was very accommodating. Our vacation was perfect.
Stayed 5 nights in Oct 2025
Verified

10/10 Excellent

Tim F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place. Close to all
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Benjamin B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place. Excellent location. Nice pool. I would stay here again.
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

Danielle C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our long weekend getaway. My family of 6 stayed for 3 nights this past weekend. The location is perfect and lots in walking distance. No worry about parking either. The pool and pool house were nice. Very quiet and clean. Condo was great for our shorter trip. Thank you!
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Liz F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Love this place! The location is amazing very close to all of the best restaurants and bars in Old Town Key West. The condo itself is very nice comfortable and clean witch is very important to me
Stayed 3 nights in Jun 2025
Verified

4/10 Poor

Vince A.

Liked: Check-in, location, listing accuracy
Disliked: Communication
This condo really needs some attention. Paint needs touch ups, knobs on doors and kitchen chairs are wobbly. Everything looks worn and the upholstered furniture needs a good wash. After the first time we ran the dishwasher it had standing water in the bottom. The ceiling fan in one bedroom had a missing pull for the fan. We had bugs in the kitchen and bathroom. It took several calls, messages to get a response. We did finally get the fan and dishwasher fixed and the exterminator came after 4 days. The notebook with instructions for the condo is falling apart and obviously outdated, for instance, the phone numbers for help aren’t correct.
Stayed 14 nights in Jan 2026
Verified

10/10 Excellent

Michael M.

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

Great place to stay

Property is in a perfect location to all key west has to offer. Clean and modern condo, we will be back.
Stayed 2 nights in Nov 2024
Verified

10/10 Excellent

Laura W.

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

Ashes

The property is clean with comfortable furniture. Great walking distance to Duval, Mallory Square & The Southernmost Point.
Stayed 2 nights in Jun 2025
Verified

8/10 Good

Kenneth M.

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

Key Condo

Very nice property in a great location, easy walk to bars, shops, beaches and the Port. Would recommend
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Ken B.

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

Perfect location

Condo was beautiful and located in the perfect location. Nice and quiet and a short walk to the fun busy town. Appreciate the stay and look forwarded to doing it again
Stayed 4 nights in Jan 2025
Verified

10/10 Excellent

Ryan O.

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

Excellent stay in Key West

Everything about the location and property was spot on. Would stay here again!
Stayed 4 nights in Dec 2023
Verified

10/10 Excellent

Katherine K.

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

Spring break

Spring break with my husband and two teens. Great proximity to everything old town has to offer. Comfy beds. Fit the 4 of us perfectly.
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

The Janet K.

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

Great location!

Excellent location, in walking distance of all the main attractions of historic Key West, yet very quiet, safe neighborhood.
Stayed 2 nights in Mar 2024
Verified

10/10 Excellent

Catherine N.

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

Nice place for a few relaxing days in Key West

Cozy place in a quiet condo very well located to visit Key West (old town, marina, southernmost point), enjoy the pool in a lovely garden, bars and restaurants and all the water activities nearby!
Stayed 2 nights in Mar 2024
Verified

10/10 Excellent

Jay D.

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

Beautiful and convenient

The property was beautiful, very nicely decorated and incredibly convenient. Loved the stay and will be back.
Stayed 4 nights in Dec 2023
Verified

10/10 Excellent

Christine B.

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

Birthday Getsway

We loved our stay! It was myself, my husband and my in laws.Clean, convenient and as advertised. We hope to return next year.
Stayed 5 nights in Mar 2025
Verified

10/10 Excellent

Melissa S.

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

Great location!

The Writer's Retreat was conveniently located near all of the Key West attractions we wanted to visit. Once we were checked in, we didn't need to move the car again until we left. The community pool was a great amenity and was located close to the unit. The apartment was the perfect size for our family of four.
Stayed 3 nights in Mar 2025
Verified

10/10 Excellent

Clayton C.

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

Perfect location

Perfect location for getting around! Nice quiet neighborhood/street and just a block away from the party. Make sure to rent bikes, best way to get around town.
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

Liz F.

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

Outstanding Location

This property is great! It’s located in a quiet area of a very active town. The property clean, safe easily accessible to Key West best shopping, restaurants and bars
Stayed 3 nights in Jun 2024
Verified

10/10 Excellent

Amy P.

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

Charming

Absolutely charming and a great location!
Stayed 2 nights in Jan 2024
Verified

8/10 Good

judith m.

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

Four sisters trip

Great location with use of the pool. Loved the second floor porches on front and rear of the unit. Tight bedrooms with one small bathroom. Cleaning crew was at our door at the 10am checkout time.
Stayed 3 nights in Apr 2025
Verified

10/10 Excellent

Mark E.

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

Wonderful stay

Completely enjoyed our stay. Great location, great place. Pictures and descriptions were very accurate. Condo was very cozy and comfy. Would highly recommend to anyone
Stayed 3 nights in Mar 2024

About the host

Hosted by Jenny Blaylock

Host profile image
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.

Why they chose this property

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 property 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.

Languages:

English
Tell us how we can improve our siteShare feedback