Experience island living in this charming 2-bedroom, 1-bath condo at Truman Annex. Relax on the balcony overlooking lush landscaping and a shared pool or take a short stroll to Duval Street, just 2 blocks away. Enjoy your favorite movies on the wall-mounted TV or unwind with loved ones in the cozy open living area.
Reviews
1010 out of 10
Exceptional
Entire condo
2 bedrooms1 bathroomSleeps 4680 sq ft
Popular amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free Wi-Fi
Add dates for prices
About this property
THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!
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.
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 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!
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Property amenities
Pool/Spa
Communal pool
Internet
Available in the condo: Free WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Microwave
Refrigerator
Toaster
Dining
Dining table
Bedrooms
2 bedrooms
Bedsheets provided
Bathroom
1 bathroom
Hair dryer
Shower
Towels provided
Living spaces
Dining table
Living room
Entertainment
TV with cable/satellite channels
Outdoor areas
Balcony
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Pets
Pet friendly
Suitability/Accessibility
Smoke-free property
Services and conveniences
Concierge services
Iron/ironing board
Location highlights
In the city centre
Near a hospital
Near the marina
Near the sea
Things to do
Basketball nearby
Birdwatching nearby
Cycling nearby
Ecotours nearby
Fishing nearby
Jet skiing nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Swimming nearby
Safety features
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)
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
Pets are allowed
Service animals are welcome, and are exempt from fees
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
On-site 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 that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
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
Property Registration Number 25230-138472
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Located by the sea, this condo is in Old Town Key West, a neighbourhood 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. Visit our Key West travel guide
Does THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! have a pool?
Yes, this property has a pool.
Is THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! pet-friendly?
Yes, pets are allowed at this property.
How much is parking at THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!?
On-site parking is available at the property.
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.
What time is check-out at THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!?
Checkout is at 10:00 AM.
Where is THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! 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. Florida Keys Beaches and Mallory Square are also within 15 minutes.
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THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers 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.
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
From a partner site
10/10 Excellent
Kim R.
29 Apr 2024
Vacation 2024
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:
Pleasant stay and good atmosphere
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
From a partner site
10/10 Excellent
Lynn C.
6 May 2024
Pelican Pearl
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
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:
Enjoyed our stay. Very professional and responsive company.
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
From a partner site
10/10 Excellent
Jeanie F.
16 Apr 2024
Awesome Condo
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:
Loved Pelican Pearl. Spent lots of time on the front porch and the back balcony when we were there. Beds very comfortable and the condo was nicely decorated. Would definitely stay here again.
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
From a partner site
10/10 Excellent
Chris C.
31 Mar 2025
Great location
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 had a great time staying in Truman Annex and The Pelican Pearl. We were a short walk from everything, the location worked great for us. The community was clean and quiet. We enjoyed many quiet mornings and evenings on the deck out back. The hosts were wonderful, couldn’t have asked for anything more.
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
From a partner site
10/10 Excellent
Marianna G.
1 Mar 2024
February 2024
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:
Truman and Company was very quick to respond when we had a few little problems. The staff was very friendly and helpful.If only there was a way to eliminate 13 steps to the second floor!
Marianna G.
From a partner site
10/10 Excellent
Anthony T.
17 Oct 2024
Key West Getaway
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:
Met all expectations.
Anthony T.
Stayed 7 nights in Oct 2024
From a partner site
10/10 Excellent
Sherri G.
6 Sept 2024
Perfection 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:
My sister and I rented the Pelican Pearl for a weeks get away.. it was absolutely perfect for us. The property is well maintained, gated for security, and other guests were friendly and courteous. The pool is chilled which means it’s a very welcomed relief from the heat!! Close to Duval but far enough you leave the madness behind. We loved it and plan on booking next year.
The property was very nice, clean, good size for 3 people; close to the pool but quiet, no loud noise anywhere. Just a couple of blocks from Duval St, walking distance to many restaurants, shops, and activities.
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!
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.
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:
Location is about three or four blocks off of Duval so it is quiet but still quick to get to where everything is happening. It is to bad the Shipyard condos will no longer be able to do short term rentals at the end of the year. I would definitely stay here again.