THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/Community Pool! | Condo in Key West

9.6 (23 Reviews) |   Pet Friendly   2 Bedrooms  1 Bathroom  4 Guests
Truman Annex Condo | THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/Community Pool!

2 Bedroom Condo in Truman Annex, Key West

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 SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/Community Pool! is located in Truman Annex. THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/Community Pool! provides accommodation, featuring Pool, View, Security/Safety, among other amenities. This Condo features Pool, View, Security/Safety, to make your stay a comfortable one.

THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/Community Pool! has 2 Bedrooms , 1 Bathroom, and max occupancy of 4 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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Amenities

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

Facility Overview

Air Conditioner
  • Air conditioning
Bathrooms
  • Towels provided
  • Bathtub or shower
  • Hair dryer
  • 1 bathroom
Bedroom
  • Bed sheets provided
  • 2 bedrooms
  • Dining table
  • Living room
Kitchen
  • Microwave
  • Oven
  • Toaster
  • Coffee/tea maker
  • Cookware/dishes/utensils
  • Refrigerator
  • Dishwasher
Laundry
  • Washing machine and dryer
  • Laundry facilities
Parking
  • Onsite parking
Pet Friendly
  • Pet friendly
Accessibility
  • Smoke-free property
Activities
  • Fishing nearby
  • Birdwatching nearby
  • Fitness facilities nearby
  • Sailing nearby
  • Marina nearby
  • Jet skiing nearby
  • Swimming nearby
  • Scuba diving nearby
  • Basketball nearby
  • Snorkeling nearby
Entertainment
  • TV with cable/satellite service
General
  • Unit size: 580 sq ft (54 sq m)
  • English
  • Near a hospital
  • In the city center
  • Near the sea
Guest Services
  • Concierge services
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Patio
  • Fenced yard
Security/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)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Deadbolt lock
  • Fire extinguisher
Spa
  • Shared/communal pool

Policies

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.
Event Policy
No events allowed
Pet Policy
Pets allowed service animals are welcome, and are exempt from fees
Smoking Policy
Smoking is not permitted

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

License number: 25230-133035

Reviews

Louise C.
Sep 29, 2025 09:25:00 AM
Review Score:   10
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: From booking, to staying, to memories made, just a wonderful property. A very pretty property..beautifully presented and spotlessly clean. The bed was so comfortable and lovely quality bedding. The Sweet Life provided everything we needed. We loved the location too... really quiet and peaceful with a well kept private terrace and great pool area but also within a few minutes walk to bars, restaurants and the park. We hired bikes and cycled to the beach too... Best of Key West were always there to help if we had any questions. Will be back for sure X
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