Florida’s Historic Hotels Get Big-Time Makeovers

To stay relevant, resorts like Casa Marina and the Boca Raton are spending millions of dollars to modernize

The Boca Raton Cloister Lobby
The Boca Raton recently spent $250 million on a phase-one renovation.
Scott Frances/The Boca Raton

Florida has a rich history of hospitality and for decades has welcomed visitors wanting to escape harsh winters. Many of its most iconic resorts were built during the Golden Age, which spanned from around 1880 to 1930, as the state transformed into a booming tourism destination. Florida then experienced another bump in the 1950s, when middle-class families began to flock to the Sunshine State for their annual vacations.

Several hotels erected during those eras have recently undergone dramatic, multi-million dollar renovations. Offering a mix of nostalgic flavor and modern amenities, these hugely upgraded, historic hotels are worth seeking out.

The Boca Raton 

Boca Raton 

The Boca Raton is a behemoth of a property that originally opened in 1926 as the Cloister Inn. The original site only had 100 rooms; nearly 100 years later, there are over 1,000 rooms, eight swimming pools and an 18-hole golf course. Spanning 200 acres, the resort includes five different properties: Cloister, Yacht Club, Bungalows, Beach Club and Tower. Last year, it underwent a $250 million dollar phase-one renovation that included the Cloister saying goodbye to its pink exterior in exchange for “coastal white,” and upping the food options to 15-plus restaurants, bars and lounges. Meanwhile, the resort’s Tower hotel saw each of its guest rooms and suites in the 27-story building newly outfitted with beachy wood furniture and luxe linens. Other recent upgrades include a new floating river and surf simulator at the resort’s four-acre water park, the Harborside Pool Club. 

Blue and white room with bed and other furniture
John Lennon, Frank Sinatra and Judy Garland have all visited the Colony Hotel under a past name
The Colony Hotel

The Colony Hotel 

Palm Beach 

Nicknamed “Pink Paradise” because of its flamingo-pink exterior, the Colony Hotel underwent a major renovation last summer that included a complete redesign of its 79 guest rooms and public spaces, with additional upgrades through this year. Originally opened in 1947 under the name the Golf View, the hotel has hosted John Lennon, Frank Sinatra and Judy Garland; the latest renovations here draw on that glamorous history while incorporating modern touches. The redesigned guest rooms are drawn together by muted pastel walls and brightly colored textiles, and some of the whimsical details include scalloped tassels that hang from the wallpaper-clad ceilings and floral embroidered headboards. Guests can also shop the rooms and bring home a slice of the property’s quintessential “Palm Beach Chic” decor. 

The Hemingway Guide to Miami and Key West
Dining, fishing, drinking and cavorting in Papa’s footsteps
Counter of a bakery in the hotel
Lottie is a French patisserie located in the Vinoy lobby
Jeff Herron Photograhy/The Vinoy

The Vinoy Resort & Golf Club, Autograph Collection 

St. Petersburg 

In its heyday, the Vinoy Resort & Golf Club in St. Petersburg welcomed stars like Babe Ruth and Marilyn Monroe, along with several U.S. presidents. The hotel, opened on New Year’s Eve in 1925, is one of the few Florida hotels listed on the National Register of Historic Places. Renovations on the hotel started in April 2023; upon arrival, guests will now be greeted by a refreshed grand lobby that still has the original ceramic flooring and cypress wood beams. Inside, the nature-inspired accommodations have soothing, sand-colored walls adorned with abstract art, and they’re outfitted with contemporary furniture. Both locals and overnight guests can take advantage of the new dining options: Lottie, a French patisserie located in the lobby, offers coffee, gelato and breakfast items; and Parasol, a Latin American-inspired restaurant that overlooks the pool deck, is great for weekend brunches. 

Walkway up to the hotel with palm trees and pools of water
Casa Marina’s $95 million renovation included adding amenities like four culinary destinations and two pools
Thomas Hart Shelby/Casa Marina

Casa Marina Key West 

Key West 

One of Key West’s most prestigious properties, Casa Marina Key West recently underwent a top-to-bottom $95 million dollar renovation and is set to reopen this month. The landmark hotel opened on New Year’s Eve in 1920 and sits on Key West’s largest private beachfront. Casa Marina was the place to be seen in Key West, attracting notable figures like Rita Hayworth and President Warren G. Harding. Upgrades to the property’s outdoor amenities include four culinary destinations, two iconic piers restored for the first time in four years and two large pools — one exclusively for adults — lined with cabanas. The new restaurants include the Canary Room, an intimate lobby lounge; and Dorada, a restaurant with 180-degree ocean views set to debut in early 2024. All 311 of the guest rooms received a refresh and many feature exposed beams, classic checkerboard tile flooring and mid-century-style furniture. 

Luxe bar area with cushion chairs and floor-to-ceiling windows
Visit the rotating Pier Top lounge when it reopens in 2024
Pier Sixty Six

Pier Sixty-Six

Fort Lauderdale 

Mark your calendars for Pier Sixty-Six’s grand reopening: The iconic Fort Lauderdale property is part of a billion-dollar revitalization project and renovations are set to wrap in late 2024. The Pier Sixty-Six hotel was built in 1957, and its unmistakable octagonal tower and spire top reshaped Fort Lauderdale’s skyline. The hotel sits on a site that started as a yachting fuel-up station in the 1950s; eventually a world-class marina was built to accommodate the boats. All 325 rooms are undergoing a redesign, and the property will also gain a 15,000-square-foot spa, a multi-level pool and 12 culinary options. Visitors will also have access to a new marina promenade that will include restaurants and retail space. The cornerstone of the redesign will include the restoration of the hotel’s famed rotating Pier Top lounge — the 17th-story bar will offer guests unparalleled views of the marina and downtown Fort Lauderdale. 


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