Truman Annex Rentals USA Florida Key West Truman Annex

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

10.0 (37 Reviews) |   1 Bedroom  1 Bathroom  2 Guests  Stay&Play
Truman Annex Condo | THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!

1 Bedroom Condo in Truman Annex, Key West

PLEASE BE AWARE...
We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nights if your arrival is 12/22 or before.
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 not a pet friendly home.
MULTI MONTH RESERVATIONS...
For monthly reservations, the following fees will be added PER MONTH:
Mid-stay clean
BOOKING DATES...
This home is only available as a monthly rental (28 night minimum) as of Dec 23, 2025. 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...

THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo! is located in Truman Annex. THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo! provides accommodation, featuring TV, Child Friendly, Laundry, among other amenities. This Condo features TV, Child Friendly, Laundry, to make your stay a comfortable one.

THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo! has 1 Bedroom , 1 Bathroom, and max occupancy of 2 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Condo because of the excellent services rendered by the owner or manager of this Condo, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Condo has a friendly neighborhood, and the Truman Annex has interesting places to visit. If you want to learn more about the Condo in Truman Annex, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pool
  • TV
  • View
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
  • Guest Services
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Pets not allowed
Smoking Policy Smoking is not permitted
Other Policy 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 host has indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited property registration number 25230-133035 safety features at this property include a fire extinguisher and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Key West, 33040, USA

What Our Guests say 500 + Reviews

Jun 13, 2025 05:13:39 AM
Summary: 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.
Tom F. Tom F.
Apr 20, 2025 08:45:10 PM
Summary: 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
Lynn F. Lynn F.
Apr 10, 2025 09:01:57 PM
Summary: 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.
Arthur H. Arthur H.
Apr 6, 2025 03:00:00 PM
Summary: 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.
Patricia C. Patricia C.
Feb 16, 2025 03:02:00 PM
Summary: 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
Mary C. Mary C.
Dec 11, 2024 10:20:43 PM
Summary: 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.
Cindy C. Cindy C.
Nov 9, 2024 12:53:27 AM
Summary: Great location
Lindsey M. Lindsey M.
Oct 9, 2024 12:27:40 AM
Summary: 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.
Felicia C. Felicia C.
Sep 20, 2024 08:22:56 PM
Summary: 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.
Charles L. Charles L.
Sep 19, 2024 01:12:00 PM
Summary: 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. Chuck L.

FAQ's

Is this Truman Annex condo pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Truman Annex condo have a swimming pool?

Yes, this Truman Annex condo has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Truman Annex condo?

Best-rates for the Truman Annex condo starts from $314 per night with includes Oceanfront, Wellness Facilities, Kitchen, TV, Child Friendly, Laundry, Parking, Pool, View, Security/Safety, Bedding/Linens, Guest Services, Air Conditioner, Ocean View, Balcony/Terrace, Internet StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Truman Annex condo a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this condo Good or guests have recommended them suitable for families. As reported by the owner or manager, the condo has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Truman Annex condo wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Truman Annex condo has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Truman Annex condo?

Based on the information reported by the owner or manager, the Truman Annex condo indicates 1 day stay policy at this condo. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Truman Annex condo?

Based on the information reported by the owner or manager, details for the cancellation policy for the Truman Annex condo are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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