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

Photo gallery for THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!

Shipyard community
Picturesque views
Steps to everything
Front porch
First floor unit

Reviews

9.6 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 4580 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

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

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen

About this property

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...
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet friendly
Free WiFi
Air conditioning

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  • Washer
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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

Is THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool! pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!?

As of Apr 1, 2026, prices found for a 1-night stay for 2 adults at THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool! on Jun 15, 2026 start from $177, 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.

How much is parking?

Onsite parking is available at the property.

What time is check-in at THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!?

Check-in begins at 4:00 PM.

What time is check-out at THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool!?

Check-out is at 10:00 AM.

Where is THE SWEET LIFE ~ Charming First Floor 2 BR/1 Ba Condo w/ Community Pool! 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

9.6

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. 20 out of 24 reviews
Rating 8 - Good. 2 out of 24 reviews
Rating 6 - Okay. 2 out of 24 reviews
Rating 4 - Poor. 0 out of 24 reviews
Rating 2 - Terrible. 0 out of 24 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Stephanie K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was as described. Would definitely come back.
Stayed 7 nights in Dec 2025
From a partner site

10/10 Excellent

Carol M.

Awesome 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: Great location that felt like home away from home!
Verified

10/10 Excellent

Judy T.

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

Excellent property and location

Wonderful property and location. First time staying here and would definitely stay here again.
Stayed 10 nights in Feb 2024
Verified

10/10 Excellent

Tim O.

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

Great Time

Great place to stay. Staff is extremely nice, quite at night and close to all that’s happening in town
Stayed 10 nights in Sep 2023
Verified

10/10 Excellent

Doug L.

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

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!
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Lee Y.

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

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.
Stayed 13 nights in Aug 2024
Verified

10/10 Excellent

Christian C.

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

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.
Stayed 7 nights in Mar 2024
Verified

6/10 Okay

Verified traveler

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

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.
Stayed 7 nights in Mar 2025
From a partner site

8/10 Good

Denise C.

Truman VRBO

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location
Stayed 7 nights in Nov 2023
Verified

10/10 Excellent

Barbara N.

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

Barbara N

It was a cozy small house. Walking distance to everything.
Stayed 11 nights in Jan 2024
Verified

10/10 Excellent

Bryan S. B.

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

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.
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Duane C.

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

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. :)
Stayed 7 nights in Jun 2023
Verified

8/10 Good

Edward M.

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

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.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Jim M.

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

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.
Stayed 7 nights in Jul 2023
From a partner site

10/10 Excellent

Louise C.

Just super in every way.

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
From a partner site

10/10 Excellent

Kim K.

Best Month In Paradise

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: Great location. Car not needed within walking distance to everything. Property was clean and appointed with things needed to make your stay comfortable. The property manager took care of any questions that we had.
Stayed 28 nights in Feb 2024
From a partner site

10/10 Excellent

Judy T.

Best Location in Key West to Stay- The Shipyard!

Rating Details: The property manager was very helpful. The vacation rental was clean. I was very happy with the location. I was satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Overall condo appeared clean when we arrived, however we did find bugs in the shower and our bed that appeared to be cockroaches. We washed all rugs and couch cover before leaving. Chair arms and cushions are dirty and could use an updating. With all that being said, the Shipyard is our favorite place to stay and are saddened to hear that we can no longer rent on a weekly basis.
Verified

6/10 Okay

Roxanne E.

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

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.
Stayed 9 nights in Apr 2025
Verified

10/10 Excellent

Cecile F.

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

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!
Stayed 8 nights in Apr 2024
Verified

10/10 Excellent

David L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Xxx
Stayed 7 nights in Aug 2025
From a partner site

10/10 Excellent

Linda C.

Our place was great! Near everything we wanted to see.

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: Place was as shown on pictures, clean and great location.
Stayed 7 nights in Oct 2024
From a partner site

10/10 Excellent

Susan R.

Best Rental

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 is the best rental I've ever had! Just the right size for 2 sisters looking for a little getaway. Great location within walking distance of almost everything on the lower half of the island. The beds were comfy, the kitchen well-equipped, and a nice living area to watch movies in at the end of a busy, sunny day. Everything was nice and clean and in good order. The unit had a washer/dryer and beach towels and plenty of linens were furnished. We are looking forward to renting again in the future.
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Madeline S.

Stayed 8 nights in Dec 2025
Verified

10/10 Excellent

Lisa S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 8 nights in Sep 2025

About the host

Hosted by Wendy Zintsmaster & Team

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