Seaside stay .Within a 10-minute walk of this Old Town Key West condo, you'll find Duval Street and Ernest Hemingway Home and Museum. Also, Mallory Square is within half a mile (1 km) and Southernmost Point is within 2 miles (3 km).
Ernest Hemingway Home and Museum - 6 min walk - 0.4 miles
Duval Street - 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
Southernmost Point - 14 min walk - 0.8 miles
Getting around
Key West Intl. Airport (EYW) - 14 min drive
Restaurants
Willie T's - 6 min walk
Santiago's Bodega - 6 min walk
Aqua - 8 min walk
Antonia's Restaurant - 6 min walk
DJ's Clam Shack - 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 PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!
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.
CHARMING 2ND FLOOR CONDO IN STUNNING "SHIPYARD" COMMUNITY OF TRUMAN ANNEX… Delight in this cozy gem of southernmost island living, a 2 bedroom, 1 bath second floor dwelling with a balcony that overlooks verdant landscaping and a sparkling shared pool! Slide on your comfiest sandals and immerse yourself in the excitement of Duval Street, just 2 blocks away. You are walking distance to the island's hot spots: Fort Zachary State Park Beach, The Green Parrot, Sloppy Joe's, Hemingway's Home and Mallory Square - home of the famous nightly "Sunset Celebration". ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS AND AMENITIES... Enter this light and airy open living area that is colorfully and tastefully decorated to ease you into a sense of well-being and tropical tranquility. You and your loved ones will enjoy a cool respite after a day in the sultry sun, sharing relaxed conversation on the cozy furnishings or decompressing with your favorite movies on the wall-mounted TV. The fully equipped and well-stocked kitchen will inspire you to practice your culinary skills, complete with granite countertops, stainless steel appliances and all the tools a chef will need. Dine or play your favorite board game at the table for 4.
SLEEPING ARRANGEMENTS… Slip into a peaceful sleep in one of the two bedrooms with plush queen beds. Both rooms offer flat screenTVs, cooling ceiling fans, clothing dressers and nightstands with power ports. The shared bathroom has been updated with a walk-in shower and there is a full washer/dryer closet for your convenience.
OUTDOOR LIVING… Open the French doors of the coastal living room to your balcony with umbrella table and chairs, a superb spot for morning coffee or dining outdoors. a second balcony resides just off the kitchen, with a lounge chair for napping or reading your favorite novel. The Shipyard in Truman Annex is a charming, tree-shrouded hideaway with serene walking paths and lanes. The beautiful community pool is lined with lounge chairs and is perfect for soaking up the Key West sun.
PARKING... This home does offer parking for one vehicle, just steps from the front door - (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 not a pet friendly home for weekly guests, however, monthly stays may bring a pet (a required $400 pet fee will be applied) that must be registered with the HOA prior to approval.
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) 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!
YOUR SLICE OF PARADISE IS CALLING...
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THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard!
THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba/ 1Ba Unit in The Shipyard!
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: 680 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
Pets
No pets allowed
Children and extra beds
Children are welcome.
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.
Property Registration Number 25230-138472
Property is also known as
2450-259285
Frequently asked questions
How close is THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! to the airport?
This condo is 4.1 mi (14-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.
Does THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! have an airport shuttle?
Airport shuttle services are not available at this condo.
How close is THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! to the beach?
This condo is a short 14-minute walk from Florida Keys Beaches and 9-minute walk from Truman Beach. Don't forget your sunscreen!
Does THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! offer free breakfast?
This condo does not offer free breakfast.
Is there a casino at THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!?
No, there is no casino at this condo.
What time is check-in at THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!?
Check-in begins at 4:00 PM.
Is there free parking at THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!?
Free parking is not available at this condo.
Does THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! have a pool?
Yes, there's a pool.
Does THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! have a spa?
There are no spa services available at this condo.
How close is THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! to downtown Key West?
This condo is 0.2 mi away from Key West.
THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! Reviews
Reviews
10
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. 22 out of 22 reviews
10 - Excellent
22
Rating 8 - Good. 0 out of 22 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 22 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 22 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 22 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Charles V.
Aug 10, 2025
Liked: Cleanliness
Very clean and location was great to get around many places nearby
Charles V.
Stayed 7 nights in Aug 2025
10/10 Excellent
Rachel R.
Aug 3, 2025
Rachel R.
Stayed 7 nights in Jun 2025
10/10 Excellent
Anne C.
Aug 2, 2025
Liked: Cleanliness
Perfect location
We were so pleased with the location- close to shops/restaurants and the best beach and sunset at Fort Zachary. We walked everywhere we wanted to go, and enjoyed the pool on hot afternoons. The condo was clean and well maintained, we were very comfortable during our stay. We’d for sure stay here again when we return!
Anne C.
Stayed 7 nights in Jul 2025
10/10 Excellent
Alan W.
Jun 26, 2025
Liked: Cleanliness
Amazing location
Close to Duval very peaceful close to fort Zackary Taylor I’ll be back!!!
Alan W.
Stayed 11 nights in Jun 2025
10/10 Excellent
Tracy A.
Jun 23, 2025
Liked: Cleanliness
Awesome! Will be back!
Awesomeness!
Tracy A.
Stayed 7 nights in May 2025
10/10 Excellent
LINDA O.
May 9, 2025
Liked: Cleanliness
GREAT LOCATION
Shipyard condos are great location in key west.one of my favs
LINDA O.
Stayed 10 nights in Apr 2025
10/10 Excellent
Charles K.
May 4, 2025
Liked: Cleanliness
Great price, Central location
Gated, secure, clean, close to all the action. Much better price than all the normal resorts.Rent bicycles at WeCycle, one block away.Have a Pina Colada at Green Parrot, one block away. Just next door, behind that, at the Big Cheeses Pub and Grub, have a really great simple smash burger.Breakfast just two or so blocks south at La Creperie or across the street from that at the historic Blue Heaven.Head back through the state park, in the opposite direction and enjoy a shaded beach and a great place to enjoy sunset.
Charles K.
Stayed 8 nights in Apr 2025
10/10 Excellent
Jocelyn T.
Jan 9, 2025
Liked: Cleanliness
Jocelyn T.
Stayed 18 nights in Dec 2024
10/10 Excellent
Nancy H.
Nov 17, 2024
Liked: Cleanliness
Great location
We had a wonderful stay and would love to have stayed longer but unfortunately we had to come home. Being there felt like home because everything was so nice. Enjoyed the 2 decks,just sitting watching the palm trees sway in the wind. Would definitely recommend to stay there.
Nancy H.
Stayed 7 nights in Oct 2024
10/10 Excellent
George B.
Sep 26, 2024
Liked: Cleanliness
Great location
Everything was perfect.
George B.
Stayed 10 nights in Sep 2024
10/10 Excellent
Mark S., Hamilton Ohio United States
Sep 24, 2024
Liked: Cleanliness
Clean, quiet second floor condo
Very nice condo in walkable part of Key West close to shopping, restaurants and entertainment. Only suggestion would be to include bicycles but rental location is only a block away.
Mark S.
Stayed 7 nights in Sep 2024
10/10 Excellent
theresa r.
Sep 5, 2024
Liked: Cleanliness
Excellent location
This is a great location. The unit is exactly as pictured.
theresa r.
Stayed 9 nights in Aug 2024
10/10 Excellent
Barbara A.
Jul 13, 2024
Liked: Cleanliness
Vacay 2024
The condo was well appointed, property management was quick to respond to the one small issue we reported. Close to everything but far enough to not be bothered with any noise. Our only complaint would be the beds - they were not comfortable at all.
Barbara A.
Stayed 7 nights in Jul 2024
10/10 Excellent
Mia W.
Jul 3, 2024
Liked: Cleanliness
Excellent home and even better location
This unit was amazing. The unit was stocked with amenities to get us started and some lasted the whole week. This unit is beautifully decorated, extremely clean, and well maintained. The Truman Annex is the best place to stay in Key West. We come here regularly and love the ease of walking to all of our favorite spots. This unit is definitely one of our favorites.
Mia W.
Stayed 7 nights in Jun 2024
10/10 Excellent
Susie R.
May 8, 2024
Liked: Cleanliness
Lovely Stay
This place has everything you need. So close to restaurants and entertainment but so quiet. The pool is great. Free parking was a plus. Easy check in and out process. Natalie was very helpful. Would definitely stay here again.
Susie R.
Stayed 10 nights in Apr 2024
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