The Best “Old” Resorts and Hotels In Florida

In Europe a hotel is not old until it passes its 200th birthday, but here in Florida old means the building was constructed before World War II.

As a historian, I enjoy the sometimes laid-back atmosphere and sheer personality of Florida’s many older resorts and hotels.  In reality, many have been so updated in facilities, wireless, the latest spa and exercise facilities, and recreational activities, they compete with the most glamorous new resorts.  Even better some of the older places have the best locations in town or on the beach.


Like A Castle In Spain Casa Monica

When I visit Saint Augustine, I easily select the 1888 Casa Monica over motel row out on A1A on the beach hotels.  Designed by noted Boston architect Frank W. Smith as the Hotel Codova but the hotel was quickly purchased by railroad magnate Henry Flagler as the “moderate resort” of his trio of Victorian masterpieces, the Casa Monica is now the only one still operating as a hotel.  The Ponce de Leon is now Flagler College and the Alcazar is a museum. The Casa Monica once served as the Courthouse of St. Johns Hotel.

Casa Monica has been restored as it was when Rockefellers and Vanderbilt’s filled the guest list.  My favorite feature of the property is it’s location directly on the City Plaza.  Walk northward into the historic district or walk southward into the wonderful Victorian section of bed and breakfasts and the Oldest House.  You are minutes from Saint Augustine’s downtown restaurants and bars.

If you like the combination of beachfront vistas and great golf facilities, I would drive north thirty minutes to the 1928 Ponte Vedra Inn.   Started by the National Lead Company for employee vacations, the complex has expanded along the Atlantiuc Ocean with 250 rooms and suites.  Across the street at the golf course and tennis complex are more recent rooms at the Lodge.


The top floor Seahorse Grill is beautiful, but the historic INN dining-room is now the breakfast nook.


At Henry Flagler’s other Victorian community Palm Beach is, of course, the famous Breakers, but I would like to suggest if you are more interested in shopping and doing the Palm Beach restaurant and night life scene to consider two smaller, highly related Florida Boom Time resorts.

It is hard to imagine that a few years ago people were talking foreclosure over The Brazilian Court.  This 80 room downtown Spanish Colonial near all the Worth Avenue shops was recently voted by Travel and Leisure the #12 Resort in the USA.  The rooms are unreal and Café Boulud is named after the restaurant’s famous chef, which attests to the quality of this place.


Urban But Sophisticated

Down the street at 363 Cocoanut Row, surrounded by glamorous stores is the four star Chesterfield, which started in 1926 as The Lido, then the Vineta.  Totally renovated in 1937 by architect John Volk, this pet friendly place is a Red Carnation Hotel.   The leathery Leopard Lounge and Restaurant is a hang-out for many of the island’s elite.


The Chesterfield of Palm Beach

Key West has a lot of quaint bed and breakfast spots and a lot of new small hotels, but if you want to step back into old Key West, you should look into the Marquesa Hotel, made from four 1884 conch houses.  The New England style complex with striped awnings does not allow kids under 14. With its suites with private terraces and old fashioned wicker furniture, this hotel is a romantic island setting.


I can’t write this article without noting the Pink Palace on Saint Petersburg Beach – the Loews Don Cesar.  Built in 1928 by Thomas Rowe and an immediate hit with people like Babe Ruth and F. Scott Fitzgerald, the resort has the best beach of any of the listed resorts.  In World War II it became a military convalescent home and then an empty landmark until rescued in 1972 by William Bowman.


The Pink Palace Of Pinellas County

The restoration turned the beachside resort into the population of several motion pictures and brought back the celebrities.  South of the resort is laidback Pass-A-Grille Beach with seafood restaurants and boat tours to the islands of Tampa Bay.

And last, a place just ten miles south of my old residence on Englewood Beach:

It’s the winter season and the 1913 Gasparilla Inn and Club on Gasparilla Island is open for business.  What makes this big white resort so special is not the shell-filled beach, but the Pete Dye golf course, the 250 slip marina, and the best tarpon fishing spot in the world.   You can stay in one of the resort rooms or in one of the 74 cottage rooms, a favorite with J. P. Morgan and Henry Ford.


Next time A Walt Disney World Food Challenge




About floridatraveler

Historian and travel writer M. C. Bob Leonard makes the Sunshine State his home base. Besides serving as content editor for several textbook publishers and as an Emeritus college professor, he moderates the FHIC at
This entry was posted in attractions, dining, environment, Florida Food, florida history, Historic Buildings, Historic Hotels & Inns, mcbobleonard, Restaurants, Tiffany and tagged , , , , , . Bookmark the permalink.

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