Located in Old Town Key West, this condo is within a 10-minute walk of popular sights such as Duval Street and Ernest Hemingway Home and Museum. The condo includes a kitchen, a patio, and a fenced private yard.
Florida Keys National Marine Sanctuary - 5 min walk - 0.3 miles
Duval Street - 6 min walk - 0.4 miles
Ernest Hemingway Home and Museum - 6 min walk - 0.4 miles
Fort Zachary Taylor Historic State Park - 8 min walk - 0.4 miles
Mallory Square - 11 min walk - 0.6 miles
Getting around
Key West Intl. Airport (EYW) - 14 min drive
Restaurants
Green Parrot Bar - 4 min walk
Blue Heaven - 8 min walk
Mangoes Restaurant - 7 min walk
Moondog Cafe & Bakery - 8 min walk
Kaya Island Eats - 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.
THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!
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.
CUTE CONDO IN STEPS FROM IT ALL… This 2 bedroom, 1 bath ground level flat 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 cozy downstairs unit has everything you'll need for your stay in paradise! ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS AND AMENITIES... Enter through the white picket fence and you are greeted by a lovely front porch with sitting area where you can sip coffee and plan your island adventures for the day. The flowing floor plan offers a spacious and lovely living and dining area that offer rest and relaxation after a day in the sultry sun and balmy breezes of the island. Whip up your favorite recipes in the fully equipped and stocked kitchen that overlooks the living area. A dining table for 4 sits next to the kitchen where you can enjoy cozy meals with your loved ones. A comfy couch, plush cushioned chairs and smart tv in the living area provide the perfect resting spot for bingeing on your latest shows and movies. A stacked laundry closet sits just off the living area for your convenience. Open the French Doors to your sweet backyard oasis.
SLEEPING ARRANGEMENTS… The first queen bedroom is on the left as you enter the home. It offers a spacious hanging closet, smart tv, and a clothing dresser for your belongings. The primary bedroom also has a queen bed, smart tv, large hanging closet and clothing dresser, and is adjacent to the full bathroom, where you can wash off the day in the shower/tub combination.
OUTDOOR LIVING… The Shipyard offers a beautiful community pool lined with lounge chairs perfect for soaking up the sun. Open the French door in the living area to the delightful private deck, a shaded retreat outfitted for unwinding and refreshment.
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 (if applicable)
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!
YOUR SWEET RETREAT...
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 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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THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
Deadbolt lock
General
Unit size: 580 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
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 welcomes pets
Service animals exempt from fees
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
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
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: 25
Property Registration Number 25230-133035
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 fire extinguisher, a smoke detector, and a deadbolt lock.
Property is also known as
2450-251510
Frequently asked questions
What's there to see within easy reach of this condo?
This condo is situated in Old Town Key West within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. You'll also find Mallory Square and Fort Zachary Taylor Historic State Park less than a mile away.
Will I be able to park at this condo?
No, this condo doesn't offer parking.
Is this condo next to a casino?
No, this condo is not connected to a casino.
Will I find an indoor pool at this condo?
No, there is no indoor pool at this condo.
What do couples enjoy most about THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!?
Couples staying at this condo will value amenities like a kitchen, kitchens in some condo units, as well as concierge services.
Does THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool! have a hot tub?
No, there isn't a spa tub at this condo.
Does this condo offer breakfast?
No, this condo doesn't offer breakfast.
Will this condo allow pets to stay free of charge?
Although pets can't stay for free, they are welcome at this condo.
Are there connecting rooms at this condo?
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 4.1 mi away (14 minutes by car).
Can I book a room with a balcony at THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!?
Yes, every condo unit at THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool! comes with a deck.
THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool! Reviews
Reviews
9.6
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 19 out of 23 reviews
10 - Excellent
19
Rating 8 - Good. 2 out of 23 reviews
8 - Good
2
Rating 6 - Okay. 2 out of 23 reviews
6 - Okay
2
Rating 4 - Poor. 0 out of 23 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 23 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Stephanie K.
Dec 21, 2025
Liked: Cleanliness
Everything was as described. Would definitely come back.
Stephanie K.
Stayed 7 nights in Dec 2025
10/10 Excellent
Lisa S.
Nov 8, 2025
Liked: Cleanliness
Lisa S.
Stayed 8 nights in Sep 2025
10/10 Excellent
David L.
Aug 24, 2025
Liked: Cleanliness
Xxx
David L.
Stayed 7 nights in Aug 2025
8/10 Good
Edward M.
Jun 28, 2025
Liked: Cleanliness
Ed Mar
Property was clean, great location, kitchen and bathroom really small, pool area good. The only concern I had was the doorway to the back patio only had a see through curtain on it. You could see inside the living room at night.That said I would still recommend the property.
Edward M.
Stayed 7 nights in Jun 2025
6/10 Okay
Roxanne E., silverdale,usa
May 5, 2025
Liked: Cleanliness
Excellent location
Unfortunately our stay was at the time they were installing a new roof on the condo's and jack hammering up the sidewalks. We had debris on our patio and constant noise. There is always maintenance that needs to be done and we understand that but it was not a peaceful experience. The condo itself was close to the pool and well equipped. It was very clean and the bed was unbelievably comfortable. It felt like a safe environment and was within walking distance of many shops and restaurants. We would not hesitate to stay here again but just hoping it's not during a major condo complex upgrade.
Roxanne E.
Stayed 9 nights in Apr 2025
6/10 Okay
Verified traveler
Apr 15, 2025
Liked: Cleanliness
Overall nice experience
A few issues that were somewhat resolved with some back and forth communication and negotiation after rainstorm damage. Location is excellent. Condo was very clean and outside area lovely.
Verified traveler
Stayed 7 nights in Mar 2025
10/10 Excellent
Doug L.
Mar 23, 2025
Liked: Cleanliness
Great time in Key West
Highly recommend the Truman Annex rental. Clean and convenient to downtown Key West with Duval Street just steps away. We had no problems or issues. Community pool was well maintained. Great place to stay!
Doug L.
Stayed 7 nights in Mar 2025
10/10 Excellent
Lee Y.
Aug 27, 2024
Liked: Cleanliness
Key West trip
Great location and stay. Just steps from the pool, easy walk to the Truman Waterfront Market or Duval, unit clean and well decorated. Communication from Melanie the property manager was excellent as we were delayed.
Lee Y.
Stayed 13 nights in Aug 2024
10/10 Excellent
Bryan S. B.
Jul 9, 2024
Liked: Cleanliness
Perfect Location!
I had the best time during my stay at The Sweet Life. If you have a bicycle you are only 5 minutes from everything at this location. The gated parking area is very nice. I felt very safe here. I intend on being back there very soon. I thoroughly enjoyed myself.
Bryan S. B.
Stayed 7 nights in Jul 2024
10/10 Excellent
Cecile F.
Apr 14, 2024
Liked: Cleanliness
Last vacation to Key West
We rented the Condo at Shipyard because of the walkability factor. It was cozy and sufficient for a 1 week stay. It was clean and nicely decorated. We came to Key West to purchase a house, which we did, so we are now on our way to becoming Freshwater Conch's.
I texted with Melanie and communication with her was great. So nice! I did use the pool at Shipyard which was nice. This is a two bedroom with queen beds and one bath so great for a family for a relaxing vacay! Thanks Melanie... It will be great to meet you!
Cecile F.
Stayed 8 nights in Apr 2024
10/10 Excellent
Christian C.
Mar 26, 2024
Liked: Cleanliness
March visit
This property is very clean, organized, great location, clean pool, full kitchen, all codes provided prior to arrival, and the host is easy to contact.
Christian C.
Stayed 7 nights in Mar 2024
10/10 Excellent
Judy T.
Mar 14, 2024
Liked: Cleanliness
Excellent property and location
Wonderful property and location. First time staying here and would definitely stay here again.
Judy T.
Stayed 10 nights in Feb 2024
10/10 Excellent
Barbara N., Holmdel
Jan 13, 2024
Liked: Cleanliness
Barbara N
It was a cozy small house. Walking distance to everything.
Barbara N.
Stayed 11 nights in Jan 2024
10/10 Excellent
Tim O.
Sep 28, 2023
Liked: Cleanliness
Great Time
Great place to stay. Staff is extremely nice, quite at night and close to all that’s happening in town
Tim O.
Stayed 10 nights in Sep 2023
10/10 Excellent
Jim M.
Jul 17, 2023
Liked: Cleanliness
Freaking awesome stay
Melanie was brilliant and responsive. Love, love, love her. Marcella was a pleasure. Fell in love with her. The condo was amazing. The location couldn’t have been better. Will be booking again and again.
Jim M.
Stayed 7 nights in Jul 2023
10/10 Excellent
Duane C.
Jul 12, 2023
Liked: Cleanliness
Family vacay
Very nice property and very clean for our family. Not super spacious but enough for 4 people. Would definitely stay here again. My only complaint is that they need more dishes and pots and pans for people who like to cook on vacation and not eat out every meal. :)