Florida's history is filled with snowbirds fleeing winter temperatures for the mild weather of the Sunshine State. Over many decades, they’ve roosted in beautifully appointed stays, leaving a legacy of storied hotels and resorts across the peninsula. In our South's Best survey, we asked our readers to vote on their favorite historic hotels in Florida, and they delivered. These spots contain layers of stories within their walls, and they also offer all the amenities that you could wish for on a beach vacation. When you visit, you may find that you never want to check out–and who could blame you? You won’t find any judgment from us if you decide to extend your trip for a few extra days. Find a few slices of history and a lot of fun in these one-of-a-kind Florida properties.
Casa Marina Hotel, Jacksonville Beach
The history of Jacksonville Beach’s Casa Marina Hotel dates to 1925. It thrived in the 1920s before being appropriated for government use during World War II. The re-opened in 1991 after many fallow years, bringing both a sense of history and a fresh new energy to its balmy corner of Jacksonville Beach. Take note of the property’s stucco facade, swaying palm trees, and cozy rooms–they lend a sense of storied elegance to the nearly century-old hotel. Learn more about Casa Marina Hotel.
Gasparilla Inn & Club, Boca Grande
You’ll never forget a visit to the Gasparilla Inn & Club in Boca Grande. It’s located on the Gulf of Mexico and has been welcoming guests since 1913. These days, visitors come for boating, sport fishing, biking, and lounging on the sands as well as special events, golfing, spa bookings, and kayaking the tranquil waterways that snake through the area. It’s also a fantastic holiday destination. Learn more about Gasparilla Inn & Club.
The Vinoy Resort and Golf Club, Autograph Collection, St. Petersburg
Opened in 1925, this historic Mediterranean Revival-style hotel recently completed the initial phase of an enormous renovation project. With its telltale pink facade and its windswept location along Tampa Bay, it welcomes visitors to St. Petersburg to enjoy golfing amid ocean breezes, dining on fresh seafood, and staying in a luxe property with a variety of lavish amenities. Learn more about The Vinoy Resort and Golf Club, Autograph Collection
Casa Monica Resort & Spa, St. Augustine
In a city with a long, rich history, you’d expect to find glorious historic hotels. St. Augustine has one of the best in Casa Monica Resort & Spa, which opened in its first iteration in 1888 and now boasts a rooftop pool, palm-planted and fountain-studded grounds, and an excellent spa. It also offers easy access to some of the city’s most interesting attractions, including the historic district, Lightner Museum, and Castillo de San Marcos. Learn more about Casa Monica Resort & Spa.
The Don CeSar, St. Petersburg
It’s no wonder The Don CeSar topped the list of The South’s Best Historic Hotels in 2023. The vibrant building dates to 1928, and its hue has earned it a few nicknames, the “Pink Palace” and the “Pink Lady” among them. When you visit, you can expect Gulf panoramas, serene white-sand beaches, a pool bar, a rooftop deck, and dining options that include the Lobby Bar and Maritana restaurant. Learn more about The Don CeSar.
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