Most places you stay when traveling are interchangeable look-alikes, hotels that could be anywhere.
You can have a unique experience, however, with these historic hotels in Florida, each with its own magic and place in Florida’s history.
You can sleep in a room once occupied by Zelda and Scott Fitzgerald; drink at a bar that once fortified Clark Gable, and admire the same waterfront viewed by US presidents.
Florida was THE place to travel from the 1880s through the 1920s, and developers thought they’d get rich building hotels that catered to wealthy visitors. The Florida land bust of the 1920s and the Great Depression of the 1930s meant few made a ton of money in the long run; some lost it all.
Many of these hotels survive. A few live on as huge and opulent palaces — five-star hotels that still cater to travelers who don’t worry about the room rate. For the rest of us, these are places to celebrate special occasions or perhaps just to admire the lobby and grand architecture.
A few others are more affordable, with interesting back stories or locations and plenty of charm.
Either way, each is one-of-a-kind.
Historic hotels of Florida’s Gulf Coast
The Don CeSar
The Don CeSar, which appears like a pink mirage as you cross onto St. Pete Beach, was railroad magnate Henry Plant’s dream. Opening in 1928 and always a striking shade of pink, it’s been known as the Pink Castle, the pink Lady or the Pink Palace. All 277 rooms were completely renovated in 1973.
Expect to find off-season rates starting at $379; look for discounts for Florida residents, seniors and others.
Only at the Don CeSar: All these things happened at the Don CeSar: In the 1932, F. Scott Fitzgerald and his wife Zelda stayed here and partied into the night; in the 1930s, the New York Yankees including Babe Ruth stayed here during Spring Training; in 1985, Tom Petty & the Heartbreakers rocked on the rooftop of the hotel for scenes for an MTV documentary.
From Florida Rambler: A guide to historic Pass-a-Grille, the Old Florida beach town home to the Don CeSar.
3400 Gulf Blvd.
St. Pete Beach, FL 33706
The Vinoy Renaissance Resort and Golf Club
In nearby St. Petersburg is The Vinoy, which opened in 1925. Famous for its pink facade and bell-tower, it was the most expensive hotel in the city at the time ($20 per night) and proudly featured a two-story ballroom and exquisite lobby. Owned by the Marriott chain today, the hotel offers a spa and golf course.
Expect to find off-season rates starting upwards of $400.
Only at the Vinoy: Both Presidents Herbert Hoover and Calvin Coolidge stayed here, as did Marilyn Monroe and New York Yankee Joe DiMaggio.
Tip for visiting: You can visit the lobby, admire the beautiful architecture and view a museum-like historic display in an alcove at the lobby’s south end. In the lobby, you’ll also find the French patisserie Lottie, which serves house-made pastries, 20 flavors of truffles and its signature Lottie Latte (made with orange essence.)
From Florida Rambler: The Vinoy is one of the stops in our story Seven things to do in St. Petersburg for an Old Florida flavor
Vinoy Renaissance Resort and Golf Club
501 5th Ave. NE
St. Petersburg, FL 33701
The Gasparilla Inn and Club
The Gasparilla Inn and Club lies in the small town of Boca Grande on Gasparilla island, and it was among the most exclusive resorts in Florida when it opened in 1913. Particularly favored by the Boston elite, references were once required prior to booking a room.
Now, a more than a hundred years later, it maintains an under-stated elegance with its palm-filled dining and sitting rooms. Nearby cottages are also available to rent. Boca Grande itself is a trip back in time with no traffic lights or gas stations and many historic homes.
Expect to find off-season rates starting at $325.
Tip for visiting: If you want to get a taste of the place, the inn’s dining room is open to the public. (But dress nice: There’s a dress code here.)
Only at the Gasparilla Inn: Some of the richest men in America have stayed here: J.P. Morgan, Henry DuPont, Florida railroad magnate Henry Plant, Henry Ford and Harvey Firestone. The extended family of George H.W. Bush, the 41st president, have stayed here annually for many years.
From Florida Rambler: Visiting Boca Grande, home of the Gasparilla Inn.
Gasparilla Inn and Club
500 Palm Ave.
Boca Grande, FL 33901
The Fenway Hotel
The Fenway Hotel in Dunedin is a gorgeous hotel overlooking the water. It was built in 1924 and it plays up its Jazz Age heritage. The lobby makes an historical exhibit out of the entrance to the original speakeasy in the basement. (It opened during Prohibition.) There’s live music in the lobby at night, and the night we visited, it was a jazzy saxophonist.
Unlike many grand Florida hotels, it remained open during World War II. Post-war, the property became the home of Trinity College for 25 years, then changed hands a few times and ended up in foreclosure in 2010.
The renovated Fenway opened in 2018 as part of Marriott’s Autograph Collection.
Today, its room prices start at $246 a night in the slow September to November period and go up to the $350 to $450 range at peak season.
Only at the Fenway Hotel: The 110-room hotel was home to radio station WGHB, the first in Pinellas County, which began broadcasting in 1925.
Tips for visiting: Even if you don’t stay at the Fenway, one of the best things to do in Dunedin is go to its rooftop bar and watch the sunset. The view over the water is perfect and the bartender leads a countdown as the sun sinks.
From Florida Rambler: The Fenway was re-opened as Dunedin was undergoing a renaissance led by the outstanding Pinellas bike trail that passes through downtown. Here are 13 things to do in Dunedin.
The Fenway Hotel
453 Edgewater Drive
Dunedin, FL 34698
The Hacienda Hotel
The Hacienda Hotel, built in 1927, again reigns as the glamorous star of downtown New Port Richey, located 50 minutes north of Tampa.
The pink stucco confection in Spanish Colonial architectural style reopened in September 2022 after decades of decay and closure.
The Hacienda is the smaller, more affordable of the three historic “pink hotels” on the Gulf Coast. (The others being the Don CeSar and the Vinoy.)
Only at the Hacienda Hotel: It debuted with fanfare with a famous comedian of the day, Ed Wynn, as master of ceremony. Soon silent-screen celebrities (many no longer household names) flocked here, including Thomas Meighan, Lupe Velez, Charlie Chaplin and Ann Harding.
Tips for visiting: Most rooms are from $140 to $170, with a king suite ideal for families going for $190 to $250. If you’re not staying here, you can stop for breakfast, lunch or dinner in the dining room or just have a drink at the hotel bar. We enjoyed taking our cocktails out to the lovely courtyard.
From Florida Rambler: The story of the Hacienda Hotel
5621 Main St.
New Port Richey, FL 34652
Historic hotels in Florida on the Atlantic Coast
Casa Monica Resort
St. Augustine’s Casa Monica Resort, originally named the Cordova Inn, was Henry Flagler’s first hotel. He purchased it from the original owner in 1888 as part of his expanding railroad empire on the Florida’s east coast. It’s appreciated today for its frescoes, fountains, and convenient location in the center of the historic district.
Off-season rates start around $300. The hotel is now part of the Marriott Autograph Collection.
Only at Casa Monica: In 1962, St. Johns County bought the then-vacant hotel and remodeled it to be the county courthouse. The building served as a government building until the 1990s, when hotelier Richard Kessler bought it and renovated it to again serve as a luxury hotel.
From Florida Rambler: Things to do in St. Augustine.
Casa Monica Resort
95 Cordova St.
St. Augustine, FL 32084
The Breakers Hotel
If you crave an unforgettable, over-the-top experience, book a room at another hotel constructed by Henry Flagler, The Breakers, the grande dame of Florida’s grand hotels, which opened in 1896.
Located in upscale, affluent Palm Beach, it was designed in Italian Renaissance style with 550 rooms and is located on 140 acres of manicured lawns, gardens, statuary, and fountains, and a half-mile of oceanfront. The painted ceiling in the lobby will take your breath away. Flagler also built himself a home not far away in 1902, which he called Whitehall, and is a museum in his honor today. If you’re in the area, don’t miss it.
Only at the Breakers: Even the golf course here is historic. One of the oldest continuously operated golf courses in Florida, it is also the first to be run by a woman. Golf pro Bessie Fenn was put in charge in 1926 and ran the golf course and club for 34 years.
Off-season rates start at $650 a night. Look for off-season specials.
From Florida Rambler: 10 ways to enjoy Palm Beach island.
1 S. County Rd.
Palm Beach, FL 33489
The Brazilian Court
Also in Palm Beach is the smaller, more intimate 80-room Brazilian Court, designed in Spanish colonial style in 1926 and likened to a Moroccan palace by Architectural Digest.
You’ll love the beautiful courtyards, fountains, and lush tropical landscaping, and you can dine on an outdoor terrace at their award-winning restaurant, too. Your pet is welcome here, and there’s even a turn-down service.
Tips for visiting the Brazilian Court: To get a glimpse of the atmosphere at the Brazilian Court, have lunch at Cafe Boulud. There’s a three-course lunch prix fixe for $49.
Off-season rates start around $500.
The Brazilian Court
301 Australian Ave.
Palm Beach, FL 33480
The Colony Hotel
The Colony Hotel and Cabana Club, with its 70 rooms right on Atlantic Avenue in Delray Beach, also opened in 1926. The Cabana Club, directly on the ocean, is two miles away. This lovely hotel is distinguished by a yellow exterior with red and yellow-striped awnings, and you’ll find many original details and furnishings inside. Family owned since 1935, the hotel prides itself on being environmentally responsible.
Only at the Colony Hotel: The interior of the hotel includes the 1926 staff-operated elevator and the original telephone switchboard. The lobby features original hand-woven Ficks Reed wicker furniture and is lit by six wood skylights.
The Colony Hotel has a summer special with rooms starting at $150.
From Florida Rambler: How to have a great weekend getaway in Delray Beach
525 E. Atlantic Ave.
Delray Beach, Fl 33483
The Boca Raton
Continuing south, you’ll find the The Boca Raton, (formerly know as the Boca Raton Resort and Club.) The hotel was named the Cloister Inn when it first opened in 1926 and you can book rooms in “the Cloister,” the historic section of the hotel.
Designed by famed “society architect” Addison Mizner to resemble Spain’s Alhambra Palace, it’s breathtakingly opulent and ornate. The Palm Court ceiling will remind you of a Victorian conservatory.)
Located on 356 acres, the hotel offers more than a thousand rooms with a choice of bungalows, towers, and suites, along with 11 restaurants and bars. Many activities are available for children and adults, and its spa was voted the best in the world.
Off-season rates start at $369. Watch for specials, such as “stay three nights; fourth night free.”
Only at the Boca Raton: The U.S. Army used the club as barracks during World War II. Called “the most elegant barracks in history,” it housed soldiers during the nearby Boca Raton Army Air Field’s operation.
Tip for visiting: The Boca Raton Historical Society offers a tour of the hotel January to May. Details.
Boca Raton Resort offers a 1.5 hour tour with an emphasis on Addison Mizner’s architectural role. Reservations required.
Boca Resort and Club
501 E. Camino Real
Boca Raton, FL 33432
The Biltmore Hotel
Further south on the east coast, George E. Merrick developed Coral Gables during these land boom years. The Biltmore, like so many hotels on this list, opened in 1926. He chose a distinctive Mediterranean Revival Style for his “city beautiful” and included elaborate entrance gates and a huge Venetian-style pool, complete with a bridge and look-out tower—still in use today. The 275 room-Biltmore Hotel was his centerpiece.
Soaring over 30 stories, it was the tallest building in Florida when 1500 guests attended the opening celebrations amid flowing champagne.
Only at the Biltmore: Like all historic hotels, there are plenty of ghost stories here. A particularly popular one is that the ghost of a gangster named Thomas “Fatty” Walsh roams the place. He was shot and killed by another gangster — on the 13th floor.
Off-season rates start at $316; there are special offers for Florida residents.
The Biltmore Hotel
1200 Anastasia Ave.
Coral Gables, FL
An equally stylish hotel can be found in Key West, the magnificent 300-room Casa Marina.
After Flagler had extended his railroad all the way to Miami, he began construction of the Overseas Railroad. This was a monumental effort in 1905, which involved importing special construction materials and hundreds of workers—and Casa Marina was vital to his plan. Billed as a “hurricane proof” hotel, it opened in 1920 and featured immense ballrooms and lavish tropical landscaping, plus a golf course and two pools.
Off-season rates start at $563.
Today it is part of Curio Collection by Hilton™.
Only at Casa Marina: The hotel was a celebrity hot-spot in the 1950s, with visitors including Gregory Peck, Ethel Merman, Ezio Pinza, Rita Hayworth and Gary Merrill. By the 1960s, however, the glamor had faded and in 1966 its owner leased the resort for use as the training location for 300 volunteers for the newly created Peace Corps.
From Florida Rambler: More about the Florida Keys
Casa Marina Hotel
1500 Reynolds St.
Key West, FL 33040
Historic hotels in Central Florida
Lakeside Inn in Mount Dora
With its big porch, fireplace in the lobby and rocking chairs overlooking the lake, this inn looks like it could be in New England. The Lakeside Inn, which opened in 1883, is the rare historic hotel that didn’t close during the Depression or WWII. It is the oldest continuously operating hotel in Florida.
When it first opened in the Victorian era, Central Florida was a popular winter destination for activities like bird watching, fishing and picnics. Over the years, the inn had fallen into serious disrepair. New owners bought it and started restoration work in 2011. The same owner more recently bought and restored the Hacienda Hotel in New Port Richey.
There are 90 rooms, a bar and restaurant. This is one a handful of historic hotels where rates are moderate. Off-season rates start at $143.
Only at the Lakeside Inn: President Calvin Coolidge and his wife stayed for more than a month in the winter of 1930.
From Florida Rambler: 12 things I love about Mount Dora
100 Alexander St.
Moun Dora, FL 32757
Historic hotels in Florida’s Panhandle
The Lodge at Wakullah Springs
Just 15 minutes south of Tallahassee, the Lodge at Wakulla Springs reminds me of the historic lodges built in the national parks, though on a more humble scale.
It dates to 1935 when a famous Floridian, businessman Ed Ball, had it built as a private lodge. (The park is officially named Ed Ball Wakulla Springs State Park.)
The elegant but rustic Wakulla Springs Lodge was built in the Mediterranean Revival style and its most special feature is a spectacular painted beamed ceiling, recently restored, in its huge lobby. The lodge overlooks the first magnitude Wakulla Springs.
The guest rooms are spacious for hotel rooms of that era, each with its own vintage marble bathroom. The rooms are all on the second floor, reachable by an antique elevator that we recommend you try out. (It functions in an unexpected way, but we’ll let you discover it.)
Only at the Lodge at Wakullah Springs: There’s an old fashioned marble soda fountain counter in the snack shop that at 70 feet 3 inches, is said to be the longest marble counter in the world.
Tips for visiting: If you don’t book a room here, you can experience the lodge by having a meal in its dining room. We found the food to be very good.
Rates start at $116 a night.
From Florida Rambler: Wakullah Springs State Park and Lodge, out of the way but worth exploring
Lodge at Wakulla Springs
550 Wakulla Park Drive
Wakulla Springs, FL 32327
Historic hotels in Florida that are no longer hotels
There were once many more grand hotels, of course, but over the decades, some have succumbed to fire, hurricanes, developer’s greed, and the ravages of time. Some, despite public outcry, have been completely demolished, like the Belleview Biltmore Hotel in Clearwater, once called the “White Queen of the Gulf.”
Others have been fortunate enough to have second lives, such as The Tampa Bay Hotel, which is now the Henry B. Plant Museum, and the Ponce de Leon Hotel in St. Augustine, now Flagler College. Both show loving and careful restoration, proud reminders of Florida’s elegant past. The historic hotel that is now Flagler College has stunning stained glass Tiffany windows and can be toured daily.
More historic hotels in Florida: Here’s the list from Historic Hotels of America, which includes several hotels from the Miami Beach Art Deco district.
The information in this article was accurate when published but may change without notice. Confirm details when planning visits.
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Bonnie Gross is co-founder of Florida Rambler. Erika J. Waters, Ph.D, who now lives part of the year in Naples, Florida, was formerly an English professor at the University of the Virgin Islands, St Croix, where she edited The Caribbean Writer and collections of fiction, poetry, literary criticism, and drama. She then taught English part-time at the University of Southern Maine, wrote books on Maine and the Virgin Islands, and was a Fulbright Scholar to Finland. Since moving to Florida, she’s taught writing and literature at the Renaissance Academy of Florida Gulf Coast University and written for the Marco Island Historical Society. She enjoys kayaking and sailing.