7 Historic Florida Hotels Everyone Should Stay at Once

From the oldest continuously operating inn to Henry Flagler’s opulent palaces

April 28, 2023 7:24 am
Yellow building in front of sidewalk near body of water
Go back in time and have the grandest stay at any of these historic Florida hotels.
Lakeside Inn

Many of Florida’s most historic hotels were built in the post-Civil War era, in an effort led by railroad and oil magnate Henry Flagler, whose name is attached to several of the grand properties below. The 1880s marked the beginning of the construction of the state’s ultra-luxurious hotels, with the 1920s and ‘30s bringing a boom in Miami’s Art Deco gems.

Whether you’re interested in a Miami Beach staycation or checking out the oldest continuously operating hotel in Florida (dating from 1883), we’ve got you covered. 

Casa Monica Resort & Spa, St. Augustine

The Moorish Revival-style Casa Monica Resort & Spa that Flagler built in 1888 has survived the test of time, from its halcyon days as a posh resort the wealthy flocked to at the turn of the century, through 30 years of neglect after the Depression shut it down. It became a courthouse in 1968, then in 2000 was restored to its original standard and reopened as a resort, with Spanish tapestries, a renowned art gallery and elegance at every turn. The spa alone makes this a worthy trip through art and history with some serious relaxation time thrown in. 

Lakeside Inn Lobby
At the Lakeside Inn, you can go fishing, kayaking or bird watching.
Lakeside Inn

Lakeside Inn, Mount Dora

Perched on the shores of Lake Dora in Central Florida is Lakeside Inn, the oldest continuously operating hotel in Florida (since 1883). Both the exteriors and interiors are part of the National Trust for Historic Preservation, so expect Victorian-era fixtures and furnishings that create an old-world feel. Bring your under-25-pound dogs, book a lakeside room and consider going fishing, kayaking, bird watching or taking a guided boat tour of this throwback to a quieter time in Florida’s history. 

The Breakers, Palm Beach

The Breakers in Palm Beach remains one of Flagler’s most impressive oceanfront resorts. Originally constructed in 1896, this massive resort had a few setbacks, with fires in 1903 and 1925, but Flagler wasn’t deterred; he hired famed New York architects Schultze and Weaver to rebuild it even bigger and better. An Italianate masterpiece with a 200-foot main lobby with frescoes painted across the ceiling, it soon became the place to be in the 1930s — and remains a spot with huge appeal for those who love luxury, complete with spa, golf course and prime oceanfront real estate.

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The Biltmore, Coral Gables

The Biltmore is another vision of architects Schultze and Weaver, this time created for hotel entrepreneur John McEntee Bowman: a “Mediterranean-style” building completed in 1926 and featuring travertine floors, massive frescoes and the huge Giralda Tower. The beauty of the Biltmore drew everyone from FDR to Al Capone (who apparently hung out in Florida all winter long in various places) and was a hotspot until World War II, when it became a U.S. Army hospital. It wasn’t until 1987 that the hotel was first restored; then in 1992, it saw a $40 million restoration that truly brought it back, including its massive marble swimming pool. It’s still a winner today.

The hallway of the Jacaranda hotel.
Caution: You might hear the voices of the ghosts of Al Capone and Babe Ruth.

The Hotel Jacaranda, Avon Park

Flagler’s railroads crossed Florida and opened up places like Avon Park in the early 1900s, which in turn drew vacationers from across America. The Hotel Jacaranda opened in 1926 with a distinctly Southern feel, with its huge veranda facing out onto Avon Park’s Main Street, comfortably furnished rooms and elegant service. Listed on the National Register of Historic Places, this is a hotel that prides itself on taking guests back to a different time in Florida’s past. Listen closely, you might just hear the ghosts of Al Capone talking to Babe Ruth, as both stayed at The Jac.

The Savoy Hotel & Beach Club, Miami Beach

This Art Deco gem built in 1935 is one of the few that has survived relatively unscathed for almost 90 years. The Savoy Hotel & Beach Club has a winning combination of beautiful design, luxurious feel and oceanfront position in Miami Beach. Today it’s actually the combination of two hotels built in the ’30s, and as a whole it’s a classic of the Miami Beach Art Deco Historic District. 

La Concha Hotel, Key West

It’s easy to imagine Ernest Hemingway hanging at La Concha’s Deco-ish bar; the 1930s-era Duval Street hotel is right in the heart of the happening Key West scene and joining the Marriott brand later this summer. So use your points, grab a lounge chair by the pool, order that tropical umbrella drink and you’ll soon find yourself melting into the historic vibe of this classic hotel.


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