A Room for the Night: Winter Haven's Hotels

The Haven Hotel opened in 1924. It was converted to 55 condominiums in 1982. Photograph by Robert Dahlgren

In December 2023, a six-story hotel opened its doors at 305 Fifth Street NW, overlooking Lake Howard in the heart of downtown Winter Haven. The Staybridge Suites, 108 rooms, modern apartments, the full amenities of a twentyfirst century extended-stay property, was welcomed as something genuinely new. It was, in fact, the first hotel to open in the downtown core in more than a century.

That the milestone felt remarkable says something about the arc of the city’s story. Because once, Winter Haven was very much a town that knew how to put a traveler up for the night.

The earliest record of lodging in Winter Haven appears in the “Florida State Gazetteer & Business Directory” of 1886–87, which listed the town’s population at one hundred souls, its amenities at two stores, a public school, a Baptist church, and a hotel. That establishment, the Central Hotel, was run by a proprietor named C. A. Boyce and is believed to have stood at the intersection of Central Avenue and Sixth Street SW, on the northwest corner of what is now a Bank of America parking lot. No clear photograph survives, though the oldest known image of Winter Haven, taken around 1890, shows a building in The Haven Hotel opened in 1924. It was converted to 55 condominiums in 1982. Photograph by Robert Dahlgren The Seminole Hotel was created when two original school buildings were moved to allow construction of Winter Haven’s first K-12 school building. The Seminole was located on the NE corner of First Street at Central Avenue. that location with a sign reading simply “Hotel.” The Winter Haven Museum holds a placard from the Central Hotel listing room rates at fifty cents, meals included.

The Seminole Hotel was created when two original school buildings were moved to allow construction of Winter Haven’s first K-12 school building. The Seminole was located on the NE corner of First Street at Central Avenue.

Across the intersection of what was then called Grand Avenue and Avenue A NW stood Mrs. Crook’s Boarding House, at the site now occupied by the Rickworth Building. In a town of one hundred, a boarding house and a hotel likely constituted the full range of options for the weary visitor.

By 1910, Winter Haven was growing, and growing more ambitious. That year, the J. N. Ackley family constructed the city’s first brick hotel, the Plaza, diagonally across US 17 from the present Bank of America. It opened with carbide lights, a modern touch for its moment; within a year, however, William Boyd brought electric generation to Winter Haven, and the Plaza was rewired accordingly. In 1910, it was estimated that there were fifteen automobiles in the entire city. Mr. Ackley was said to own one of them.

By 1914 or so, the city was preparing to build its first combined K–12 school on the site of what is now the downtown post office, a $30,000 project that would finally allow Winter Haven students to complete their education without traveling to Orlando or DeLand. As construction got underway, two older wooden school buildings were relocated across First Street to the east, where they were converted into the Seminole Hotel, operated by Ella Johnston.

The most celebrated of Winter Haven’s early hotels, however, was still to come.

In 1921, two prominent residents, R. H. Ross and J. Walker Pope, father of the man who would one day found Cypress Gardens, decided the growing city deserved a proper hotel. They sold stock to local residents and broke ground, but funds ran short before the walls were even up. For a time, only the iron framework stood, a skeleton of ambition over an empty lot. Bonds were sold to complete the financing, and construction resumed.

By late October 1924, the building was ready. On a sunny autumn day, 350 of Winter Haven’s then 1,600 residents gathered to celebrate the opening of a six-story structure built of coquina shell, looking out over Lake Howard. The “Florida Chief,” forerunner of the “News Chief,” called it “one of the most magnificent in the country.” They called it The Haven Hotel.

The Plaza Hotel on the NW corner of the intersection of Central Avenue and 6th Street, N.W. It was the city’s first brick structure.

T. L. Hobart and Harry P. Dye held the major interest in the hotel at its completion. Dye, who had previously managed a hotel in Birmingham, Alabama, took charge of operations from the start. He would have had little trouble filling rooms. The Florida land boom was in full cry, and trainloads of northern speculators arrived regularly as guests of the Haven-Villa Corporation, an enterprise managed by a man named George Dick, who traveled the country delivering testimonials about the paradise that awaited in Winter Haven. Those who came at his invitation were lodged at The Haven, wined and dined, and for a time, at least, many purchased their own small piece of Florida sunshine.

The boom years brought a proliferation of lodging options throughout the city. By the mid-1920s, Winter Haven could boast fourteen hotels in all. Downtown alone offered several notable establishments. The Roseart Hotel stood on Third Street NW at Avenue B NW, on the site now occupied by the Ambulatory Surgery Center, and advertised itself as “the first hotel in the world with a radio in every room.” The Lake Region Hotel opened in 1926 and, after decades of use, was repurposed during the 1980s as a downtown office building by developer William “Bill” Raley.

At the northern edge of downtown, Henry G. McCutcheon, who had arrived in 1919 and would serve as Winter Haven’s mayor from 1924 to 1927, built the Ridgeland Hotel around 1925. It stood diagonally across from what is now the Sixth Street McDonald’s well into the 1960s; the site today is home to a CVS Pharmacy.

The Lake Region Hotel is now home to downtown offices.

The boom, of course, did not last. The collapse of the Florida land market in the late 1920s, followed by the Great Depression and then the disruptions of World War II, reshaped the city’s economy and its hospitality landscape alike. As Cypress Gardens drew tourists to Winter Haven in the postwar years, smaller motor courts and roadside motels multiplied along the approaches to the attraction, and the grand old downtown establishments gradually faded. The Haven Hotel itself endured longer than most, serving guests for decades before being remodeled into condominiums in 1982. The handsome old coquina shell building still stands above Lake Howard today, now home to fifty-five residences, a quiet testament to the ambitions of those 350 residents who gathered on a warm October afternoon a century ago to celebrate something they believed their city deserved.

In December 2023, Winter Haven once again had a hotel in its downtown core. The Staybridge Suites rose on Fifth Street NW where, not far away, Mrs. Crook once ran her boarding house and C. A. Boyce offered a room and a meal for fifty cents. The names have changed, and the rates considerably more so. But the impulse, to welcome the traveler, to offer a place to rest, to say this city is worth a stay, is as old as the town itself.