11 Incredible Historic Hotels In Florida

In a state filled with luxurious resorts and hotels offering beyond-the-world experiences, those that emanate “Old Florida” essence are held especially high in regard. Leaving one speechless just from looking at them, one will never forget the experience of staying or forgive themselves for not visiting one of these incredible historical hotels, given a chance.

Fontainebleau, Miami Beach

Fontainebleau, Miami Beach. Editorial credit: Felix Mizioznikov / Shutterstock.com

Designed by the legendary architect Morris Lapidus and built in 1954, the modernistic hotel is considered an architectural wonder and arguably, the most famous historic hotel in the state. With its prime Miami Beach oceanfront location, Fontainbleau has been featured in countless movies, including the James Bond classic, “Goldfinger.” Striking in design, with 1,504 renovated rooms and a complete range of spa and luxury facilities, its premier property spreads over 20 acres in the lively atmosphere at the heart of the Millionaire’s Row.

Casa Marina Resort, Key West

Casa marina resort florida
Guests in Pool at Casa Marina Waldorf Astoria.

The conception of the magnificent 300-room Resort took place upon Flagler’s extension of the railroad to Miami when he began the construction of the Overseas Railroad. The realization of the railroad took much effort back in 1905, including importing special construction materials and hundreds of workers, with Casa Marina part of his master plan. He built it as a “hurricane-proof” hotel with immense ballrooms, lush tropical landscaping, a golf course, and two pools. Erected in 1921 on the beach in the Old Town Key West, Casa Marina Resort is owned by the Waldorf chain of hotels and listed on the National Register of Historic Places.  

Casa Monica Resort & Spa, An Autograph Collection, St. Augustine

Casa monica resort and spa
Casa Monica resort and spa building in St. Augustine. Editorial credit: Kristi Blokhin / Shutterstock.com

With St. Augustine as the oldest continuously occupied European settlement in the United States, it is considered a cultural honor that the city of such high regard embraced Casa Monica Resort & Spa. The hotel was opened in 1888 as Flagler’s first, under the name “Cordova Inn,” to attract business to his expanding railroad onto Florida’s east coast. Restored to its past glory, the Moorish Revival-style hotel features original artwork in the hand-painted Italian tiles, Spanish tapestries, frescoes, and golf-leafed archways. Set in the heart of the downtown with a grand fountain in front, it is part of the Marriott Autograph Collection. The rooms known for their “elegance at its finest” have hosted the King and Queen of Spain, while there are also the Costa Brave Mediterranean restaurant, the Cobalt Lounge, and the luxurious Poseidon Spa.  

Colony Hotel & Cabana Club, Delray Beach

olony Hotel and Cabana Club. Delray Beach, Florida, United States.
Colony Hotel and Cabana Club. Delray Beach, Florida, United States. Editorial credit: alisafarov / Shutterstock.com

The incredible hotel was designed by an associate of Addison Mizner and built in 1926 in the romantic signature style of the Flagler era, known for Florida Mediterranean architecture. The three bright yellow stories topped by twin domed towers feature the classic resort-vibe yellow-and-red-striped awnings hinting at Old Florida. Centrally set in Delray Beach’s vibrant downtown in the surroundings of stylish boutiques, restaurants, and galleries, there is also the Colony Porch Bar and retail store entrances from Atlantic Avenue into the building. The eco- and pet-friendly hotel is a family-owned and operated Colony Hotel, a chain known for bold features, tropical décor, and high-tech amenities. The Colony Cabaña Club offers a private beach and various pools with a tropically-infused atmosphere of the swaying palms, arching sea grapes, and ocean breezes. 

Don CeSar, St. Pete Beach

Don CeSar
Don CeSar, St. Pete Beach. Editorial credit: VIAVAL TOURS / Shutterstock.com

The luxury Mediterranean-style hotel on the sugary sands of St. Pete Beach Island, in the Gulf of Mexico, was built in 1928 to resemble a castle, with an instant claim-to-fame as “Florida’s Pink Castle.” With its European grandeur, seaside elegance, and the enchantment of the bygone days, the hotel is the epitome of America’s traditional beach resorts at sunsets. Having played host to various celebrities, including F. Scott Fitzgerald, it is no surprise that the hotel highlights the opulent Gatsby-era with its Moorish components and lush landscaping. The 10-story masterpiece with balconies and terraces features the renovated 277 luxury rooms and 36 suites, two heated pools, Spa Oceana, and enticing seafood at the Maritana Grille restaurant. 

Gasparilla Inn, Boca Grande

Gasparilla Inn, Boca Grande. Image credit: PVSBond via Wikimedia Commons

The hotel dates back to 1913, when the mega-wealthy traveled in personal railroad cars, with Boca Grande as their favorite hideaway. The Gasparilla Inn hosted the likes of Henry Ford, the late President George H.W. Bush, Harvey Firestone, Thomas Edison, and Katharine Hepburn. Set at the heart of the island, the premier destination features a pale yellow wooden frame and Victorian-style gable roofs. Upon stepping through the pillared entrance into the lobby, guests get instantly tranquilized by the Old Floridian vibe of the classic resort from the yesteryear. The 163 charming hotel rooms and cottages open seasonally from October to July offer breathtaking views of the Gulf of Mexico and Charlotte Harbor. The resort amenities include the Pete Dye championship golf course and the beach club with a full-service spa, a salon, and its own private beach.

Belleview Inn, St. Petersburg

Belleview Inn was built by the railroad and steamship entrepreneur of the 19th century, Henry B. Plant. The magnate believed that his clientele base of passengers would grow if they had a place to stay upon arriving via one of his new railways into St. Petersburg. Erecting a palatial Queen Anne-style Victorian hotel in 1897, “Belleview” exuded the grandeur of the Gilded Age. Quickly gaining a vast reputation among its haunted crowd of the rich and the famous, it hosted many Hollywood celebrities throughout the years. Expending accordingly to its growing popularity, the final measurement of 400,000 square feet made it the largest wooden-frame structure in the state for many years. Renamed “Belleview Inn” in 2018, one of America’s most incredible historic hotels is known among the top charming retreats in the country today. 

La Concha Hotel & Spa, Key West

La Concha Hotel
Tourists walking in front of the La Concha Hotel and Spa in Key West.

Literary legends and dignitaries like Ernest Hemingway, Tennessee Williams, and President Harry S. Truman found contentment and inspiration in Key West’s scenic beauty and rich culture. Screaming of history and playfully notorious nightlife, La Concha Hotel & Spa was opened to serve guests on Duval Street on the island. The peacock-colored ceilings and dark wood furnishings were inspired by the desirable location, while the emanating vintage charm and contemporary elegance are accentuated through the esteemed, highly-personalized service of the hotel. Bringing the history of Key West back to life, there is also a haunting legend that it has hosted guests long gone.

The Breakers, Palm Beach

The Breakers
The exterior of Breakers Hotel in West Palm Beach. Editorial credit: Sean Pavone / Shutterstock.com

Built by Henry Flagler in 1896 for the travelers of his new Florida East Coast Railway, it was rebuilt times again to manifest into its restored version today as a magnificent luxury hotel. Located on 140 acres of manicured lawns, gardens, statuary, fountains, and a half-mile of oceanfront, staying at one of its 550 rooms makes for an unforgettable, over-the-top experience. Known as the “Grande dame of Florida’s grand hotels,” the upscale location complements the Italian Renaissance design, including the breathtaking painted ceiling of the lobby. Known as the more affordable of the luxury bunch, there is also the Whitehall museum nearby that Flagler built as his homestead in 1902.

The Chesterfield Palm Beach, Palm Beach

Built in 1926 on the palm-lined boulevards, the 53-room boutique hotel and historic landmark in Palm Beach emanates Southern coastal charm. Having existed under several names, it is set proximate to the Worth Avenue shopping, while the white sandy beaches of Palm Beach are practically at its doors. Each room adorned with Coolidge colors is individually decorated to resemble the high-end European-style bed and breakfast. The old-world charm of The Chesterfield comprises a romantic couple’s stay where one can get the Queen’s treat of the afternoon traditional high tea. Set in one of Florida’s wealthiest towns, the local architectural icon is known for English charm and top-notch service. 

The Vinoy Renaissance St. Petersburg Resort & Golf Club, St. Petersburg

Vinoy Renaissance
The Vinoy Renaissance St. Petersburg Resort & Golf Club. Editorial credit: Joseph Sohm / Shutterstock.com

Commissioned by the Pennsylvania businessman Aymer Vinoy Laughner in 1923, the architect Henry L. Taylor designed the hotel to reflect the grandeur of the golden age as a salmon-colored Mediterranean Revival building overlooking the Tampa Bay. Worth $3.5 million to erect, The Vinoy Park Hotel proudly opened on New Year’s Eve in 1925 with 362 luxurious guestrooms but struggled in the years leading up to WWII. By the time it closed from disrepair for over 20 years in 1974, it had hosted the likes of Calvin Coolidge, Herbert Hoover, Marilyn Monroe, and Babe Ruth. Upon undergoing $93 million worth of restoration and expansion efforts, one of Florida’s most luxurious resorts now features a guest tower, a 74-slip marina, and an 18-hole golf course.  

Emanating the dominant presence of age, these hotels need not beg to be admired. Their absorbing atmospheres and the complementing extravagant locale will leave lasting memories.