7 Midcentury Florida Hotels That Have Changed But Don't Skimp On Nostalgic Charm

Florida has long lured travelers with the promise of abundant sunshine, a tropical climate, and miles of sandy beaches. While the Sunshine State's gorgeous natural landscape is the obvious star, Florida's distinctive architecture and unique design are also worth the journey south. Here, amidst palm-fringed islands and energetic cities, you'll find hotels that capture the spirit of the era in which they were built. One of these eras is the midcentury period, when Florida's tourism flourished and a futuristic aesthetic was adopted post-war. During this time, many of Florida's exciting new hotels welcomed a buzzworthy cast of guests, from royals and presidents to musicians and actors.

In the 1940s, Miami gave rise to the Miami Modern (MiMo) movement, exemplified by its towering hotels with modular, geometric architecture. Around the same time, an abundance of roadside motels catering to the post-war road trip crowd were built up and down the coast. While some of these iconic resorts have faded with the sands of time, others have evolved to stay current. Renovated and refreshed with chic interiors, inviting swimming pools, stylish restaurants, and luxe amenities, these midcentury hotels are now firmly in the 21st century. However, these hotels have also preserved and celebrated the nostalgic charms that made them legendary. Today, you can walk in the footsteps of Frank Sinatra at his favorite hotel in Miami Beach, or sidle up to the same hotel bar where Jimmy Buffet first performed in Key West.

For the traveler who wants to turn back the clock a few decades without sacrificing comfort and style, here are seven midcentury hotels worth visiting on your next Florida vacation.

Fontainebleau Miami Beach, with its iconic white crescent-shaped tower overlooking the ocean, was designed by Morris Lapidus in the 1950s, and was the largest example of the MiMo architectural style at the time. The Fontainebleau became the center of glamorous nightlife in midcentury Miami and drew glittering performers. It was one of Frank Sinatra's favorite places to stay and served as the film set for many movies, including the James Bond film "Goldfinger" in 1964. The resort has expanded significantly over the following decades, but the hotel's iconic original tower and theatrical interiors continue to be a hub for entertainment.

Rising above Fort Lauderdale's network of canals, Pier Sixty-Six was the hotel that gasoline built. The Phillips Petroleum gas company was behind the 17-story hotel, which debuted in 1965 and was designed in the futuristic "Googie" style that was popular at the time. Its most distinctive feature was the rotating rooftop lounge, which was frequented by celebrities. In 2025, the hotel unveiled a multibillion-dollar renovation, upgrading the 325 rooms and suites with a fresh take on midcentury style and expanding its super yacht marina. Guests seeking a true blast from the past should ascend to the revamped — and still revolving – Pier Top Lounge.

Islamorada, a Florida Keys village known as the "Sportfishing Capital of the World," has drawn ambitious anglers for well over a century. Cocooned between the Overseas Highway and the Atlantic Ocean, the Islander Resort was once the private fishing domain of Florida developer Henry Flagler. In the 1950s, the new owner built a low-slung retreat on the property, signaled by a Space Age-themed sign right along the famous highway. The original sign still headlines the entrance today, though what lies beyond the lush greenery is a renovated Florida Keys oasis with breezy suites and bungalows, beachfront dining, a cabana-lined swimming pool, and water sports.

The Sunset Inn and Cabanas occupy a beachfront block in Treasure Island, a low-key St. Petersburg suburb with white sand shores. This gem of a 1940s motel was originally known as the Coral Lee and was transformed into a boutique adults-only hideaway in 2022. The four guest rooms are decorated with a neon-hued color palette, and some even feature picture windows overlooking the Gulf. The heart of the motel is anchored by a sparkling swimming pool and lined with colorful retro cabanas that are available for day rentals.

Travelers cruising down Miami's Biscayne Boulevard can't miss the whimsical Vagabond Motel sign presiding over the busy thoroughfare. Turn into the motor court of The Vagabond Hotel and revert back to 1953, the year color televisions were first sold and Corvettes hit the road. Originally designed as an elevated version of the highway motel, the Vagabond was famed for its innovative architecture and mermaid-tiled pool. Around 2012, the white and turquoise-hued motel was restored to its midcentury glory with 42 refreshed accommodations featuring throwback furnishings and the original swimming pool surrounded by colorful loungers. 

With a prominent perch near Worth Avenue, the pink-tinted Colony Hotel has been a Palm Beach icon since opening in 1947. Over the following decades, The Colony hosted the elite island's high society and was even immortalized in a midcentury Slim Aarons photograph. While the pink facade remains unchanged, the Colony's interiors were stylishly upgraded in recent years, now featuring jungle-inspired wallpaper in the lobby and an airy coastal-chic design in the rooms, suites, and villas. Outside, the daily scene by the swimming pool and the indoor-outdoor Swifty's restaurant still appears plucked from an effortlessly cool Slim Aarons photo.

Key West's historic architecture, waterfront setting, and swashbuckling spirit have made this eclectic island a beloved destination. In the 1960s, one of Key West's foremost preservationists, David Wolkowsky, envisioned Pier House, a low-key motel at 1 Duval Street. Situated on Key West's legendary thoroughfare with a sliver of sandy beach, Pier House became especially famous for its Chart Room Bar, where Jimmy Buffet made his debut in 1971. Over the years, Pier House has modernized and expanded to nearly 150 accommodations and an on-site spa, but its original amenities, such as its courtyard swimming pool and the convivial Chart Room Bar, still remain.