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

Key West, Florida
$182 avg/night Minimum Stay 2 Nights
Bed 1

Bed

Bath 1

Bath

Home Condo

Property Type

Sleep 2

Max Sleeps

Night 2 nights

Min Stay

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...

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    1 Bedroom Bed Sheets Provided
  • GENERAL

    Unit Size: 580 Sq Ft (54 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Terrace
  • POOL/SPA

    Heated Pool Shared/communal Pool
  • BATHROOMS

    1 Bathroom Hair Dryer Shower Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Birdwatching Nearby Cycling Nearby Fishing Nearby Fitness Facilities Nearby Jet Skiing Nearby Marina Nearby Sailing Nearby Scuba Diving Nearby Swimming Nearby
  • ENTERTAINMENT

    TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    In The City Center Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Concierge Services Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 2

Map Map

School District Rates & Availability

Review Review

  • David K.

    Submitted Dec 5, 2025

    Stayed Nov 25, 2025

    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.

  • Chris S.

    Submitted Nov 11, 2025

    Stayed Oct 19, 2025

    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.

  • Wendy S.

    Submitted Oct 14, 2025

    Stayed Jun 13, 2025

    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

  • Gary E.

    Submitted Aug 17, 2025

    Stayed May 12, 2025

    Great, clean and centrally located

  • Christian S.

    Submitted Aug 12, 2025

    Stayed Jul 20, 2025

    Great location and amenities. The property manager had great communication and the check-in and check-out processes were well timed and easy.

  • Libby C.

    Submitted Jul 15, 2025

    Stayed Jul 4, 2025

    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.

  • Tom F.

    Submitted Jun 12, 2025

    Stayed May 25, 2025

    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.

  • Lynn F.

    Submitted Apr 20, 2025

    Stayed Apr 13, 2025

    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

  • Arthur H.

    Submitted Apr 10, 2025

    Stayed Mar 22, 2025

    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.

  • Patricia C.

    Submitted Apr 6, 2025

    Stayed Mar 29, 2025

    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.

  • Mary C.

    Submitted Feb 16, 2025

    Stayed Jan 11, 2025

    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

  • Cindy C.

    Submitted Dec 11, 2024

    Stayed Nov 23, 2024

    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: This unit is very comfortable and offers all the comforts of home. The deck is huge and allows privacy due to all of the beautiful landscaping at Truman Annex. The management team and staff honestly are over the top in their attention and response from the time I booked the property until I checked out. I was absolutely 110% satisfied and I am not usually easy to please.

  • Lindsey M.

    Submitted Nov 8, 2024

    Stayed Oct 18, 2024

    Great location

  • Felicia C.

    Submitted Oct 8, 2024

    Stayed Sep 27, 2024

    The place is ok if you’re looking for the basics and no frills. Nice location. Needs a deep cleaning and a remodel. Would have preferred not to be solicited (twice) by the management company for their real estate pitches. There are similar properties in the area at a better price. Side note: owner had me pay off of Vrbo which made me very uncomfortable and I don’t think it’s within their policies. Just a heads up.

  • Charles L.

    Submitted Sep 20, 2024

    Stayed Dec 31, 1969

    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: Staying in the Truman Annex is an easy way to experience Key West. Great location, quiet and well maintained property. The unit was excellent for the 2 of us on a week stay. This is slow season because of the brutal heat, potential for storms and lots of places are closed for the month. Plenty to do though, so if smaller crowds are your thing, this would be a great time.

  • Chuck L.

    Submitted Sep 19, 2024

    Stayed Sep 11, 2024

    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: Staying in the Truman Annex is an easy way to experience Key West. Great location, quiet and well maintained property. The unit was excellent for the 2 of us on a week stay. This is slow season because of the brutal heat, potential for storms and lots of places are closed for the month. Plenty to do though, so if smaller crowds are your thing, this would be a great time.

  • leGay C.

    Submitted Sep 8, 2024

    Stayed Aug 31, 2024

    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!

  • Greg G.

    Submitted Aug 20, 2024

    Stayed Aug 9, 2024

    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.

  • Rita W.

    Submitted Jul 10, 2024

    Stayed Jul 3, 2024

    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!

  • Dale L.

    Submitted Jul 3, 2024

    Stayed Jun 26, 2024

    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.

  • Agnes A.

    Submitted Jun 13, 2024

    Stayed Jun 3, 2024

    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: This condo was perfect and just the right size for us. The location was perfect and close to everything. It was clean and they had everything we needed for our week stay! We will stay again if we come back to Key West!

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Total

Includes taxes and fees
$182+
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