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THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!

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Welcome to Paradise!
A picturesque stroll through the neighborhood
Your peaceful retreat awaits
Sunny days ahead
Step into your island home

Reviews

9.8 out of 10
Exceptional
1 bedroom1 bathroomSleeps 2580 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪6 min walk‬
  • Place, Ernest Hemingway Home and Museum
    ‪6 min walk‬
  • Place, Fort Zachary Taylor Historic State Park
    ‪8 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪13 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom 1

1 King Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Dining area

About this property

THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!

PLEASE BE ADVISED IF BOOKING THIS UNIT FOR AUGUST 2026: The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. The HOA expects the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. There is no other pool available at the Shipyard, so we have adjusted our rates to offset the inconvenience.

COZY VALUE IN TRUMAN ANNEX…
This 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the coveted Truman Annex in the heart of Old Town Key West! You will be in walking distance from Fort Zachary’s gorgeous beach and picnic area, Duval Street, Mallory Square and more! Throw your cares to the wind as you unwind in this charming, tree-shrouded neighborhood with walking paths and lanes. This small but sensational gem is an upstairs unit with all of the creature comforts you will need in paradise!
***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE

DETAILS AND AMENITIES...
Easy breezy comfort greets you as you enter this charming home. Travel up the carpeted stairs to a bright and cheerful open living room and kitchen/dining space. Unwind on the plush furnishings as cheerful sunlight floods the living room and creates a happy and carefree environment. A smart TV offers a wide array of programming for your viewing indulgence. The dining/kitchen area is adjacent to the living room, with a dining table nearby. The kitchen is fully equipped with a dishwasher, stove, microwave, refrigerator and both a Keurig and drip coffee maker. The cabinets are stocked with every kitchen tool you will need to craft delicious meals.

SLEEPING ARRANGEMENTS…
Unwind from your day of island fun in the king bedroom. A wall-mounted smart tv is available for lazy days when it just feels right to linger in your cozy bedding and binge on your favorite shows. The storage closet houses a fold-up twin bed and extra bath linens for your enjoyment. The bathroom is next door with a glass-door shower and a washer/dryer closet is adjacent to it for your convenience.

OUTDOOR LIVING…
The Shipyard offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Open the French door to the roomy private terrace, inviting sultry breezes and Key West sunshine inside. This wonderful extension to the living space has a table for 2 where you can have your morning coffee or enjoy a cocktail after a long day of exploring. There are also 2 more cushioned wicker chairs for lounging outdoors.

PARKING...
This home does offer parking for one vehicle (vehicle cannot exceed 18 ft), but oversized trucks and extra large SUVs are not permitted and will have to park outside of this community.

PETS...
This is a pet friendly home with a required pet fee. Please include the size and breed when inquiring.

MULTI MONTH RESERVATIONS...
For monthly reservations, the following fees will be added PER MONTH:
Mid-stay clean
Pet fee

BOOKING DATES...
This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.

CANCELLATION...
Bookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.

CONCIERGE SERVICES...
Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!

COME STAY A WHILE...
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet friendly
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed
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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
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
Property Registration Number 25230-133035

About the neighborhood

Key West

Located by the sea, 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 Florida Keys Eco - Discovery Center are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
Map
Key West, FL

What's nearby

  • Florida Keys National Marine Sanctuary - 5 min walk - 0.4 km
  • Duval Street - 6 min walk - 0.5 km
  • Ernest Hemingway Home and Museum - 6 min walk - 0.5 km
  • Fort Zachary Taylor Historic State Park - 8 min walk - 0.7 km
  • Mallory Square - 11 min walk - 1.0 km

Getting around

  • Key West Intl. Airport (EYW) - 14 min drive

Restaurants

  • ‪Green Parrot Bar - ‬4 min walk
  • ‪Willie T's - ‬6 min walk
  • ‪Mangoes Restaurant - ‬7 min walk
  • ‪Blue Heaven - ‬8 min walk
  • ‪Rams Head Southernmost - ‬7 min walk

Frequently asked questions

Does THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo! have a pool?

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

How much does it cost to stay at THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!?

As of Apr 1, 2026, prices found for a 1-night stay for 2 adults at THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo! on Apr 5, 2026 start from $157, 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 THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo! pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!?

Check-in begins at 4:00 PM.

What time is check-out at THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!?

Check-out is at 10:00 AM.

Where is THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo! located?

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

Reviews

9.8

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. 39 out of 42 reviews
Rating 8 - Good. 1 out of 42 reviews
Rating 6 - Okay. 1 out of 42 reviews
Rating 4 - Poor. 0 out of 42 reviews
Rating 2 - Terrible. 1 out of 42 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Gary E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great, clean and centrally located
Stayed 9 nights in May 2025
Verified

10/10 Excellent

Chris S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The accommodations and amenities were wonderful! The balcony was very large and nice. Would have like a couple loungers up there but it was very accommodating. The location was a short walk to Duval but it was also very private and quiet. We highly recommend this place.
Stayed 7 nights in Oct 2025
Verified

10/10 Excellent

Christian S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and amenities. The property manager had great communication and the check-in and check-out processes were well timed and easy.
Stayed 12 nights in Jul 2025
Verified

10/10 Excellent

Lindsey M.

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

Great spot

Great location
Stayed 10 nights in Oct 2024
Verified

10/10 Excellent

David K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Whitney was awesome, she even came over to help us with the electronic door lock! Will definitely call her if we come back. Thanks for everything.
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Arthur H.

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

KW Good Life

Our stay at The Good Life was just that! The location was perfect with an easy walk to Old Town and a quick golf cart ride to the beaches. We are looking forward to our next trip to Key West.
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Libby C.

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

Terrific stay in Truman Annex

This condo is in the perfect location in Key West. Easy access to all the hot spots. Just rent a bike or golf cart and you’re on your way. It was a great space as well. Perfect for the two of us, and loved having a washer and dryer since we were there for 11 days.
Stayed 11 nights in Jul 2025
Verified

10/10 Excellent

Karen

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

Great place

The condo was beautifully decorated and well equipped. We loved the privacy. May stay here again!
Stayed 7 nights in May 2023
Verified

10/10 Excellent

Connie R.

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

The Good life

Loved the location as we have stayed in this area before. Was able to walk to entertainment, events and great food. Great place to relax but close to many favorite spots.
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

Rita W.

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

Peaceful and Close to Everything

We really loved this well-appointed condo in the Truman Annex. The neighborhood was beautiful, the place clean and comfortable, and the location was great—close to Duval St, beaches and historic sites. Would definitely stay here again!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Laura P.

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

Cozy and quiet, yet close to everything

Truman Annex is gorgeous with a friendly neighborhood feel. The apartment is just perfect for 2.
Stayed 9 nights in Nov 2023
Verified

10/10 Excellent

Tom F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved the condo and the location!! Very clean and great AC. Communication with the host was perfect and promptly. We rented bikes and they were delivered and picked up at our condo. Location was close to everything! Would definitely stay here again.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Larry B.

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

Loved it!

Great place and location. Very clean and comfy King Bed
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

Wendy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a fantastic place to stay. Perfect for the husband and to celebrate our anniversary! Great location, just a short walk to Duvall St. Great bars and food near by. No need to rent a car while you are everything is a pretty easy walk. You can spend the morning on Duvall or expeditions and then come back and jump into the pool for a cooling off and then you are ready for the evening. So peaceful, can't hear much noise at all. It was a perfect place. WE WILL BE BACK
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

leGay C.

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

26th Anniversary

5th stay @Truman Annex and this was the best by far! Looks even happier in person. Perfectly appointed with everything we needed to feel at home for the week!
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Denise A.

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

Total relaxation

Great spot near the park and Duval. Was totally relaxed the whole week.
Stayed 7 nights in Feb 2024
Verified

10/10 Excellent

Lynn F.

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

Amazing

The Good Life is a hidden gem! Clean and comfortable. Location couldn't be any better to walk to everything on Duval. Gated community with a designated parking spot was a plus. WwilTrumanAnnex m
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Lori L.

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

The Good Life

The Good Life is a great name for the property. The Truman Annex is beautiful and in a great location. All details of property are accurate and the deck is so nice to have. Would definitely book again.
Stayed 7 nights in Jan 2024
Verified

10/10 Excellent

James F.

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

The good life

Lovely condo! Huge and very nice back deck! Great KW location! Love the Shipyard condos and Truman Annex is perfect location for all things Key West Old Towne!
Stayed 7 nights in Jan 2024
From a partner site

10/10 Excellent

Patricia C.

Cozy, clean Truman Annex condo, just right !

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We so enjoyed our stay in this clean, comfortable , bright, quiet home in the beautiful Truman Annex neighborhood of just close enough to the beach and downtown , and the folks we met at the community pool were warm and pleasant.
Verified

10/10 Excellent

Greg G.

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

Perfect

What a delightful vacation. Melanie was so helpful and responsive. The condo was clean, comfy, quiet and in the perfect location. We will only stay at Truman Annex from now on! Looking forward to our next visit.
Stayed 8 nights in Aug 2024
From a partner site

10/10 Excellent

Mary C.

Cozy retreat

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We spent three weeks at the good life and thoroughly enjoyed it. Our favorite spot, the balcony, very private, and very comfortable. A great location for Key West Key West
Verified

10/10 Excellent

Kelly R.

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

Great location in Key West

We’ve been to the Keys a dozen times and this is the best location so far. If you like a short walk to Duvall, this is the place to stay. It’s a quiet complex and the balcony view is spectacular, not to mention the roominess out there. The condo is clean and updated as well. Fort Zachary is a 15 minute walk or a quick bike ride. We would stay again.
Stayed 7 nights in Apr 2024
Verified

10/10 Excellent

Dale L.

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

Quiet and convenient

Very quiet and beautiful property. Liked the added touches. Pool is a little small with the number of people staying there. It’s a 3 minute walk to The Green Parrot. Easy walk to most places.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Joyce M.

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

Delightful getaway

We thoroughly enjoyed our time in this beautiful little condo. We loved the decor and especially the fabulous, large porch. The Property Manager was very responsive. The only hitch was that we had a hard time finding the unit initially, but after that it was smooth sailing!
Stayed 7 nights in Feb 2024

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