Dripping in old-school glamour, coastal views, and juicy past lives, these Florida waterfront hotels serve history with a side of sunshine. Check in for vintage charm, iconic architecture, and maybe a ghost or two.
The Breakers Palm Beach
Built in 1896 by railroad tycoon Henry Flagler and rebuilt in 1926 after a fire, The Breakers in Palm Beach is a Renaissance Revival dream. The moment you walk in, you’re met with soaring hand-painted ceilings, Italian marble underfoot, and a lobby that feels lifted from a Florentine palace. Take a dip in one of the resort’s four pools, tee off at two championship golf courses, and dine at any of the nine restaurants. To relax, sun on a private beach, and treat yourself at the highly-rated spa.
The Vinoy Resort & Golf Club, Autograph Collection
If pink stucco walls and Mediterranean arches could talk, The Vinoy in St. Petersburg would have nearly a century of star-studded stories to tell. Since opening in 1926, it’s welcomed everyone from Babe Ruth to U.S. Presidents, all drawn to its marina views and Moorish-inspired design. Inside, original cypress beams and striking Chihuly glass accents create a seamless mix of history and modern flair. Play a few sets on the tennis court, then clean up for a sunset waterfront dinner, complete with live jazz in the background.
Casa Marina Key West, Curio Collection by Hilton
Built in 1920 on the quiet side of Old Town Key West, Casa Marina is where tropical tranquility meets Roaring ‘20s elegance. Designed by famed architect Thomas Hastings (of New York Public Library fame), it once served as the winter playground for the elite – Hemingway included. Stroll more than a thousand feet of private beach and lush gardens, splash about in two oceanfront pools, and take in the view of the setting sun over the sea from the pier with a luxurious ocean breeze in the air.
The Don CeSar
Nicknamed the “Pink Palace,” The Don CeSar in St. Pete Beach has been stopping beachgoers in their tracks since 1928 with its flamingo-pink grandeur and Mediterranean-inspired domes. This icon served as a military hospital in WWII and was later restored to its Jazz Age glory, complete with terrazzo floors, grand staircases, and dripping chandeliers. Find award-winning dining, a full spa, beachfront cabanas, live music echoing from the lobby, and the ghost of the founder wandering the halls.
Lakeside Inn
Florida’s oldest continuously operating hotel since 1883, Lakeside Inn in Mount Dora is a laid-back, charming spot to escape the everyday hustle. Its butter-yellow clapboard buildings, white rocking chairs, and wraparound verandas perched right on the lake invite you to slow down and stay a while. Presidents like Calvin Coolidge stayed here, and today, you can enjoy sailing excursions, antique shopping in the nearby village, and evening cocktails under 130-year-old oaks strung with fairy lights.
National Hotel
Right on Collins Avenue in Miami Beach and dripping in 1939 Art Deco glory, the National Hotel blends sultry curves, vintage glamour, and a pool game that’s hard to beat. Inside, the original terrazzo floors and chrome details sing of Miami’s golden age, while the modern 205-foot infinity pool – the longest in South Beach – sets the vibe for chic lounging. Explore hidden courtyards, get lost in art-filled halls, and saddle up to a speakeasy-style bar to order an elegant espresso martini.
Bayfront Marin House
Bayfront Marin House is historic hospitality at its warmest, overlooking Matanzas Bay in the heart of the nation’s oldest city. Housed in an 18th-century-style inn (rebuilt with love and painstaking historical accuracy), it feels like a step back in time, complete with clawfoot tubs, antique furniture, and complimentary wine hours. Relax on a private porch or balcony, watch seagulls drift over the horizon, and take a short walk into Castillo de San Marcos and the cobblestone streets of Old Town.
Casa Faena
Originally built in 1928, Casa Faena brings Mediterranean Revival charm and boho soul to Miami Beach. With Spanish tile floors, mosaic accents, red clay roof tiles, and wrought-iron balconies, the building itself is a romantic relic. Inside, vintage elegance meets modern quirk with antique trunks, eclectic art, and a living room-style lobby. Access amenities from the larger Faena Hotel nearby, including beach service, a luxe spa, and nightly live entertainment.
