Entire condo

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

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

A beach with a wooden signpost listing distances to various cities. - Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom (Key West)
A gated property with a sign for Shipyard Condominiums. - Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom (Key West)
A wooden deck with lounge chairs and a table, surrounded by a white picket fence and palm trees. - Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom (Key West)
A living room with a sofa, a coffee table, a TV, a ceiling fan, a mirror, and a view of a patio with a bicycle. - Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom (Key West)
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a white picket fence. - Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom (Key West)
Close to Duval Street and Mallory Square, Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom provides a playground, laundry facilities and more. Active travellers can enjoy cycling at this condo. Stay connected with free in-room WiFi.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

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

  • Welcome to Keys to Paradise – Your Cosy 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 favourite 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, chest of drawers, full-length mirror, and a flat screen Firestick TV.

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

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

    Laundry Closet: Washing machine, 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 bathroom 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.

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About the area

Located in Old Town Key West, a neighbourhood in Key West, this condo is near theme parks and by the sea. Fort Zachary Taylor Historic State Park and Ernest Hemingway Home and Museum are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and South Beach. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. Kayaking and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby. Visit our Key West travel guide
View more Condo rentals in Key West
Map
Key West, FL

What's nearby

  • A military jet flying low over a concrete path surrounded by vegetation.
    Key West Naval Station
    4 min walk - 0.4 km
  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    6 min walk - 0.5 km
  • A coastal fortification with a staircase leading to a higher platform, overlooking the sea.
    Fort Zachary Taylor Historic State Park
    8 min walk - 0.7 km
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    9 min walk - 0.8 km
  • A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.
    Mallory Square
    11 min walk - 0.9 km

Getting around

  • Key West, FL (EYW-Key West Intl.)
    15 min drive

Restaurants

  • Margaritaville
    7 min walk
  • Green Parrot Bar
    4 min walk
  • Blue Heaven
    9 min walk
  • Mangoes Restaurant
    7 min walk
  • Jack Flats
    7 min walk

Frequently asked questions

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

Yes, this property has an outdoor pool.

Is Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom pet-friendly?

No, pets are not allowed at this property.

How much is parking at Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom?

On-site parking is available at the property.

What time is check-in at Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom?

Check-in begins at 4:00 PM.

What time is check-out at Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom?

Checkout is at 10:00 AM.

Where is Keys to Paradise - Shipyard Truman Annex 2 Bedroom / 1 Bathroom located?

Located in Old Town Key West, this condo building is within a 10-minute walk of Truman Waterfront Park, Duval Street and Fort Zachary Taylor Historic State Park. Florida Keys Beaches and Mallory Square are also within 15 minutes.

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Reviews

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

9.6

Exceptional

9.6

Cleanliness

10

Location

7.0

Property conditions & facilities
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

Reviews

Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

8/10 Good

Liked: Check-in, communication, location

Some improvements

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

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Great

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

10/10 Excellent

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

Work vacation

Great time
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Mrs

Good
Stayed 8 nights in Aug 2023
Verified review

6/10 Okay

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Great stay

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

10/10 Excellent

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

Wonderful

Would happily stay again
Stayed 7 nights in Oct 2022
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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