Skip to Content

The Old Man and the Sea Inn Unit B#




Siesta Key, , US

Property Images
Property Images
Property Images
Property Images
Property Images

Entire Apartment in Siesta Key,

4 guests · 1 bedrooms · 1 bathrooms









Min Stay:


Eight Steps to the Sand Path of Siestas Best Beach! - Old Man and the Sea Inn (2). Rated The World's Finest, Whitest Sand at the Great International Sand Challe…
This is the Old Man and the Sea, a Gertrude Rentals property! This Key-West-style Victorian is just 8 steps to the sand path of Siesta Key’s best beach. We DON’T have thru traffic, commercial businesses, or public parking.  We DO have hammocks, dormers, westerly facing decks, gingerbread cutouts, brightly colored columns, tropical plants, al-fresco dining, the top snorkeling fishing and kayaking on the island, and a beach holding the title “Best Sand Winner” at the Great International Sand Challenge.  Perfect for travelers in search of that rare combination of uncomplicated-seclusion and the worlds best beach. The Location - Escape the institutional feel of hotel-condos and commerciality of Village shops, and sleep with Gertrude’s Old Man. No car required. Walk to the top beaches, eco-activities and dining including the highest rated seafood, ice-cream, daiquiris, and Siesta’s only waterfront dining. The closest beach is a cove with the calmest/clearest water on the island. Fifty yards south is a limestone reef with tide pools, colorful marine life, miniature conch, chameleons, “usually” dolphin, and “occasionally” turtle, that is perfect for exploring by foot, snorkeling, fishing, paddle-boarding or kayak.  If you prefer relaxation above activities you can sleep on the beach, sit in the ocean, sun on the west balcony, swing in the hammocks, or walk to town for drinks at the Daiquiri Deck, Sniki-Tiki, or Orange Octopus. Each unit has a fully equipped kitchen, there is a gas grill downstairs, and you can find fresh fish at Crescent Market or catch your own nearby.History - The Old Man and the Sea Inn is a Key West Victorian dedicated to both my father Captain Allison Van-Lopik “Van” Jones and the Santiago character from the book with the same name. One believed in luck and one didn’t, only one had radar but neither had GPS, still both made a life on the ocean and with endurance strength and humility.Support Post Booking - I understand vacation time is precious and my job is to make sure you get the most out of it.  My number is the only contact information you need. My units are already at the top attractions on the island.  Cars are never required, but if you have one you get a private parking space. Check-in any day of the week at any time using your private door-code. No requirement ever at checkout. Free early/late check-in/check-out, whenever possible.  Never hidden fees or solicitations of any kind. No paper contracts and easy booking.  I’ll phone you to touch base after booking and the week vacation starts. Five days before arrival I’ll email instructions including your door-code address and guidebook. One day prior to arrival I’ll send you a “Reminder” email with all the same information.When you book with me you get a fully accessible and knowledgeable owner/host and reliable advice from a Google approved local expert. I can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, Eco-tourism, family friendly activities, or safe ways to lose your kids when you need a break. For the less extroverted, every booking comes with an unabashed guidebook detailing the property, all my favorite things to do in the area, and never any advertisements or solicitations. This is the only rental offering of its kind on the key.Cleaning - This is a 100% private unit, with a private kitchen, private laundry, private AC system, and private medical air purifier.  The unit is deep cleaned with the anti-virals, has its AC filters changed for each stay, and has a dedicated Medify brand medical grade germicidal air purifier system capable of cleaning air in units nearly 4 times this size, and yes everyone wears masks and gloves while working.  Further when you enter the unit you will see we have removed excess items like rugs, throws, curtains, and even knickknacks.Terms - *We do not allow cancellations and all reservation payments are non-refundable, however travel insurance is available to address any issue you might have.  *Events or gath


Bird Watching

Cable TV

Near Beach



Outdoor Shower

Gas Grill


Symphony Orchestra

Golf Course

$ 97

/ night

Save $43/night





Check in

Check out

You won’t be charged yet

4.5 (2 reviews)#














February 2021

Bill M. Our stay was actually more than we hoped for. The unit was just as the pictures reflect and exactly what a beach place should be. Dan could not have been any more helpful. We look forward to returning to the very same unit! Loved it!


March 2021

Carol M. We stayed in Siesta Key at The Old Man and the Sea February 2021 and what a great time we had. We were in a one BR. It felt much bigger. Everything we wanted or needed was there. Accommodations were very clean, so pretty... And only a few steps to the beautiful beach. We could walk to restaurants the Tiki bar within 10 minutes. We enjoyed it so much we are going back in April. What you see in the photos is just what you see when you arrive. Dan is “the man” and took great care of us while we were there and for our return visit.


Siesta Key, , US

Things to know

House rules

Check-in: 4 PM

Check out: 10 AM

Pets are allowed

No smoking

No parties

Health & safety

All Whimstay properties are professionally managed and verified

Carbon monoxide alarm

Smoke alarm