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!
YOUR SLICE OF PARADISE IS CALLING...
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Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
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Truman Annex
Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
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
Property Registration Number 25230-138472
About the area
Key West
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. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
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, FL (EYW-Key West Intl.) - 14 min drive
Restaurants
Green Parrot Bar - 4 min walk
Mangoes Restaurant - 7 min walk
Blue Heaven - 8 min walk
Rams Head Southernmost - 7 min walk
Moondog Cafe & Bakery - 8 min walk
Frequently asked questions
Does THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! have a pool?
Yes, this property has a pool.
How much does it cost to stay at THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex!?
As of 18 Apr, 2026, prices found for a 1-night stay for 2 adults at THE PELICAN PEARL ~ Charming 2 BR/1 Ba Condo in Truman Annex! on 1 Jun, 2026 start from S$191, 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.
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.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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.
laura g.
Stayed 7 nights in Sep 2025
Response from VrboOwner on 23 Oct, 2025
Laura, what a joy to read your review—thank you so much! We’re so glad you loved your time in Key West and can’t wait to have you back on the island soon.
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
Response from VrboOwner on 1 Sept, 2025
Thank you for your wonderful review! We’re so glad you enjoyed the unbeatable location, with easy access to shops, restaurants, Fort Zachary beach, and those beautiful sunsets. It’s great to hear the condo was clean, comfortable, and well maintained, and that you could cool off in the pool after your walks. We’d be delighted to host you again on your next visit to Key West!
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
Response from VrboOwner on 1 Sept, 2025
Thank you for your kind review! We’re so glad you felt right at home and enjoyed the comfort of the property, especially relaxing on the decks and taking in the palm trees. We wish your stay could have been longer too, and we’d love to welcome you back anytime you return to Key West!
From a partner site
10/10 Excellent
Jeff M.
4 Nov, 2025
Nice condo in a 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:
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.
Jeff M.
Response from VrboOwner on 7 Nov, 2025
Jeff, we’re so glad you had a great time with us, it was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
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
Response from VrboOwner on 23 Jul, 2024
We are so happy to read you had such a good stay with us Susie! We would love to welcome you back!
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
Kim R.
Response from VrboOwner on 24 Jul, 2024
Kin, thank you for this short and sweet five star review, we hope to have the pleasure to host you again next time you visit the island.
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.
Lynn C.
Response from VrboOwner on 24 Jul, 2024
Thank you for your review Lynn. We are so thrilled to hear how much you loved this home and hope to see you again!
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
Response from VrboOwner on 23 Jul, 2024
Thank you for your wonderful review Mia. We enjoyed hosting you and hope to see you back in Key West again soon!
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
Response from VrboOwner on 1 Sept, 2025
Thank you for your great review! We’re so glad you enjoyed the convenient location, the value compared to resorts, and all the wonderful nearby spots you discovered. From bike rentals to local restaurants and sunsets at the state park, it sounds like you made the most of your Key West stay. We’d love to welcome you back for another visit!
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.
Jeanie F.
Response from VrboOwner on 24 Jul, 2024
Thank you for your review Jeanie, we are so glad the property met your needs while staying with us. We hope you'll stay with us again next time you visit Key West.
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.
Chris C.
Response from VrboOwner on 2 Sept, 2025
Thank you for your kind words! We’re so glad you enjoyed your stay at The Pelican Pearl and that the location, peaceful community, and relaxing deck made your trip so enjoyable. It’s wonderful to hear our team could help make your stay seamless, and we’d love to welcome you back anytime!
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.
Response from VrboOwner on 2 Mar, 2024
Thank you for your wonderful review Marianna. It was a pleasure hosting you and we hope to welcome you again next time you visit paradise!
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.
Sherri G.
Stayed 7 nights in Aug 2024
About the host
Hosted by Wendy Zintsmaster & Team
Languages:
English
Premier Host
They consistently provide great experiences for their guests