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Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom

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Photo gallery for Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom

Sun loungers, beach towels
Smart TV
Terrace/patio
Children's area
Outdoor pool

Reviews

9.6 out of 10
Exceptional

Entire condo

2 bedrooms1 bathroomSleeps 4680 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

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.)
    ‪15 min drive‬

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About the neighborhood

Key West

Located in Old Town Key West, this condo is within a 10-minute walk of popular sights such as Duval Street and Fort Zachary Taylor Historic State Park. The condo includes a kitchen, a patio, and a fenced private yard.
View more Condo Rentals in Key WestOpens in a new window

What's nearby

  • Florida Keys Eco - Discovery Center - 3 min walk - 0.2 miles
  • Florida Keys National Marine Sanctuary - 5 min walk - 0.3 miles
  • Duval Street - 6 min walk - 0.4 miles
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles
  • Ernest Hemingway Home and Museum - 9 min walk - 0.5 miles

Getting around

  • Key West Intl. Airport (EYW) - 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

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom

Welcome to Keys to Paradise – Your Cozy Retreat in the Heart of Key West!

Located in the charming Shipyard Condominium Complex at Truman Annex, this quaint and well-appointed first-floor condo offers the perfect blend of comfort and convenience. Featuring two bedrooms and one bathroom, it’s ideal for families or friends looking to explore Key West’s best attractions just steps away!

Inside Your Home Away From Home:

Spacious Living Area: Relax on new full-size sofa (sleeper included), two comfy chairs, and enjoy your favorite shows on the 50” flat screen TV.

Dining Room: Full-size table with seating for four—perfect for meals or game nights.

Fully Equipped Kitchen: Includes refrigerator, dishwasher, oven, coffee maker, blender, toaster, and all the essentials you need.

Guest Bedroom: Two twin beds that can convert into a king on request, a closet, dresser, full-length mirror, and a flat screen Firestick TV.

Master Bedroom: Queen bed, 50” flat screen TV, closet, dresser, and full-length mirror.

Bathroom: Full-size shower/tub combo, vanity, and toilet.

Laundry Closet: Washer, dryer, and cleaning supplies for your convenience.

Step Outside:

Enjoy a huge back deck with seating, a table, umbrella, and two cruiser bikes to explore the island. Lush, mature landscaping surrounds the condo, creating a serene environment with walking paths and easy pedestrian access through Truman Annex.

Community Perks:

Assigned parking spot right in front of your unit.

Secure gated community with code entry.

Pool area with loungers, towels, and restroom access.

Access to Truman Annex pedestrian gates via foot gate keys.

Prime Location:

Walk or bike less than 2 blocks to Truman’s Little Whitehouse and the iconic Green Parrot. Less than 1 mile from Fort Zachary Taylor Beach, Mallory Square, Duval Street, the Southernmost Point, Hemingway House, and more!

Leave your car behind and enjoy Key West at your own pace. Whether it’s your first visit or a beloved return, Keys to Paradise offers the ideal home base for your unforgettable island getaway.
The condo is air-conditioned and features a kitchen and a patio, and there's space to spread out with 2 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a fenced private yard, and a coffee maker.

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Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Communal pool
  • Fenced private pool
  • Outdoor pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Fenced yard
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • No elevator
  • Smoking not allowed

Services and conveniences

  • Concierge services
  • Iron/ironing board

Location highlights

  • In the city center
  • Near the marina
  • Near the sea

Things to do

  • Bicycles
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling nearby
  • Swimming nearby
  • Theme park nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Unit size: 680 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 28

Check-out

Check-out before 10:00 AM
Contactless check-out available

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
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 fire extinguisher, a first aid kit, and a deadbolt lock
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 28

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Additional information about polices, regulations, and more:

  • Long-term renters welcome.
  • There are no elevators.

Property is also known as

Keys to Paradise - Shipyard Truman Annex Key West
Keys to Paradise - Shipyard Truman Annex Private vacation home

Frequently asked questions

What is there to do close to this condo?

This condo is situated in Old Town Key West within a 10-minute walk of Duval Street, Fort Zachary Taylor Historic State Park, and Ernest Hemingway Home and Museum. You'll also find Florida Keys Beaches and Southernmost Point less than a mile away.

Is there parking available at Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom?

No, there isn't parking available at the condo.

Is this condo associated with a casino?

No, this condo is not connected to a casino.

Will I find an indoor pool at this condo?

No, this condo doesn't have an indoor pool; however, there is an outdoor pool.

Is Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom good for couples?

Amenities that appeal to couples at this historic condo include a kitchen and a smart TV along with an outdoor pool.

Does Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom have a hot tub?

No, this condo doesn't have a spa tub.

Does this condo include breakfast service?

No, this condo doesn't offer breakfast.

Will this condo allow pets to stay for free?

No, pets aren't allowed at this condo.

Does Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom have connecting rooms available?

No, this condo doesn't feature connecting guestrooms.

How far is the airport from this condo?

The closest major airport to this condo is Key West Intl. Airport (EYW), which is 4.3 mi away (15 minutes by car).

Are there rooms with balconies at Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom?

Yes, every condo at Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom comes with a patio.

Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 29 out of 36 reviews
Rating 8 - Good. 5 out of 36 reviews
Rating 6 - Okay. 1 out of 36 reviews
Rating 4 - Poor. 1 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

9.6/10

Cleanliness

8.0/10

Amenities

7.0/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Janet

Liked: Cleanliness, amenities, property conditions & facilities, communication
Great location! Nice pool area and the unit was spotless. Would Recommend
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Moore F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay. The condo was clean and well supplied with towels, bikes and beach gear. We had no issues and would definitely recommend this to anyone who is looking for a place to getaway.
Stayed 7 nights in Jan 2026
Verified

10/10 Excellent

Diane R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice rental. Close to everything.
Stayed 21 nights in Feb 2026
Verified

10/10 Excellent

DAVID C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice place
Stayed 8 nights in Oct 2025
Verified

10/10 Excellent

Laura S.

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

Wonderful Stay

Cute, clean condo and great location. Enjoyed it very much and would book again.
Stayed 9 nights in Oct 2024
Verified

10/10 Excellent

Anne B.

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

Cozy & close to a lot

Nice place, great location, enjoyed the stay, thanks.
Stayed 7 nights in May 2024
Verified

8/10 Good

Anita L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our two week stay at Keys to Paradise.Pros: location couldnt be better; walkable to everything, nice patio, bikes were a plus, comfortable mattresses, clean and well stocked.Cons: the unit could use a bit of an update; a bit "tired". Some new beach towels would be nice, another skillet and new microwave would be nice. A great addition would be a grill but I do understand its just another thing to have to care for. Overall it was a comfortable stay.
Stayed 14 nights in Jan 2026
Verified

10/10 Excellent

Benjamin P.

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

Great Location

Very clean, modern and great location to everything you want to see. Four bikes on premises to use makes it extremely easy to explore.
Stayed 8 nights in Jan 2025
Verified

10/10 Excellent

Karen R.

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

Great Condo

This property is perfect for a small group. It was clean throughout and the back yard was nice to sit in the morning with our tea. Perfect location - can walk to everything!
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

Jan M.

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

Key West

Great location! Beautiful grounds! Nice condo with nice amenities! The owner was attentive to our needs!
Stayed 7 nights in Apr 2024
Verified

10/10 Excellent

Cheryl C.

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

Great

We had a great time!
Stayed 10 nights in Jan 2023
Verified

10/10 Excellent

Kerri M.

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

Work vacation

Great time
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Lee O.

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

Nice christmas

Had granddaughters fly down for one of our three weeks. Great tome and great location.
Stayed 20 nights in Dec 2022
Verified

8/10 Good

Aaron P.

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

Location Location Location

Nice 2 bedroom ground floor condominium. Walking distance from Fort Zachary state park, Truman waterfront, and tons of restaurants and bars. Really nice backyard space, quiet and beautiful. Furniture and appliances are a bit dated but the grounds are great and well maintained. People are friendly and the location cannot be beat in Key West.
Stayed 21 nights in Feb 2025
Verified

8/10 Good

Linda B.

Liked: Check-in, communication, location

Some improvements

Location is wonderful. Interior of unit needs some upgrades.
Stayed 9 nights in Feb 2024
Verified

10/10 Excellent

BRANDI S.

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

Great communication and clean unit

If you are looking for good communication, a clean unit and easy walking distance to Duval street. This is for you. Stayed for 9 nights.
Stayed 9 nights in Sep 2024
Verified

10/10 Excellent

Tiffani G.

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

Fantastic!

Truly the best location for exploring key west! We felt very safe and secure in this gated complex with our children. The grounds are beautiful, as is the condo! The bikes are a great bonus - as you will probably leave your car parked and just ride and explore everywhere! We will return to this condo without a doubt for our next key west fix!
Stayed 7 nights in Dec 2021
Verified

10/10 Excellent

Kerri M.

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

Mrs

Good
Stayed 8 nights in Aug 2023
Verified

6/10 Okay

Jeff G.

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

Anniversary Trip

The Shipyard Truman Annex was a great location for a seven day stay in Key West. The area is quiet, but close to all that is offered in Key West. If you enjoy walking, you can watch the sunrise in the morning, walk to a State Park, shop in the afternoon, have a nice dinner along the water, and watch a beautiful sunset in the evening. The condo was nice but had a few issues that will cause us to give the unit a overall score of 3.5. The queen bed in the master bedroom was horrible and we could survive one night in the bed. On the second night we tried the sleeper sofa and were forced out of the bed after one night due to another worn out mattress. By the third night we were forced to the second bedroom and used the twin beds for the rest of our stay. The condo provided bikes and beach chairs that we used on our trip to the State Park. The bikes are in need of minor work but served the purpose. The unit above ours had guests the first two nights and we could hear them into the early hours of the morning. After they left the unit was vacant the rest of the week and noice was not a problem. For our first time to Key West this area was enjoyable.
Stayed 7 nights in May 2023
Verified

10/10 Excellent

Nanci K.

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

Great place and location!

Near downtown and the beach at Zachary state park! Cute place. Nice patio.
Stayed 8 nights in Nov 2022
Verified

10/10 Excellent

Alexis B.

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

Great stay

Great place, great location, great stay!!
Stayed 7 nights in Nov 2022
Verified

10/10 Excellent

Paul S.

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

Wonderful

Would happily stay again
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

jeffry k.

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

Great Location

Convenient to everything. Nice pool. Bikes needed some work. Very clean. Enjoyed our stay
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

Les M.

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

Close to it all!

Excellent location close to everything we like. Safe area only a block from the courthouse. Good sized TVs and everything worked.
Stayed 7 nights in May 2022
Verified

10/10 Excellent

Dennis M.

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

Excellent property!

2nd visit. The cleanliness was superb. Also, appreciated the new washer/dryer, the beach chairs, bicycles, liquid hand soap at both kitchen (with new sponge) and bath, quality bath towels, beach towels, paper towels, and laundry and dish detergent. The only noticeable issue (which has nothing to do with owner) was the quality of the pool water which seemed dirty with little evidence of being circulated through filtration.
Stayed 9 nights in Apr 2022

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