Here’s a riddle for you: What do Walt Disney, Lyndon B. Johnson, the Minnesota Twins, Danny Thomas, and about a thousand poolside partygoers have in common? They all walked through the doors of the Cherry Plaza Hotel in downtown Orlando, a nine-story building on Lake Eola that somehow managed to be a luxury hotel, a civil rights flashpoint, a nightclub, a presidential suite, and the single most important press conference venue in Florida history, all before quietly turning back into an apartment complex like nothing ever happened.
If buildings could write memoirs, the Cherry Plaza Hotel would have a bestseller on its hands. For roughly half a century, this lakefront tower on the south shore of Lake Eola served as Orlando’s unofficial headquarters for everything, big announcements, bigger parties, baseball drama, and at least one evening where the most powerful man on the planet decided this was the best place in town to crash for the night.
Today it goes by MAA Parkside, and it’s back to being apartments. But the stories packed inside those concrete walls? Buckle up.
Table of Contents
How a Radio Guy Turned Apartments Into the Cherry Plaza Hotel
Our story starts in 1950, when a shiny new nine-story apartment tower called Eola Plaza popped up on the Orlando skyline. Designed by architect Garry A. Boyle and built by the Paul Smith Construction Company, it was one of the tallest buildings in a city that was still mostly two-story houses and orange groves. The thing had nearly 200 feet of lakefront frontage on Lake Eola, and almost every unit came with a water view. Not a bad gig for 1950.
Enter William Cherry, a broadcaster and businessman whose Cherry Broadcasting company owned WDBO-AM, WDBO-FM, and WDBO-TV. Cherry looked at this apartment building in the mid-1950s and had one of those lightbulb moments: Orlando’s visitor numbers were surging, air travel was taking off, and the city was desperately short on hotel rooms. He had a building full of rooms. You can guess what happened next.
Cherry bought Eola Plaza, chopped up some of the bigger apartments, slapped his name on it, and added a 1,200-seat convention facility that included a ballroom called the Egyptian Room and a nightclub called the Bamboo Room. Just like that, the Cherry Plaza Hotel was open for business, and it quickly became the swankiest address in town. The Minnesota Twins would later call it the best hotel in Orlando, which is the kind of endorsement you’d put on a billboard if you could.
That Time the President of the United States Slept Over
October 1964. A presidential motorcade rolls through downtown Orlando, and out steps Lyndon B. Johnson — the actual sitting President of the United States — at the front door of the Cherry Plaza Hotel. He proceeds to spend more than 20 minutes shaking hands and working the crowd on the sidewalk before heading inside, because apparently that’s just what LBJ did.
This was a big deal. It was the first time a sitting U.S. president had ever spent the night in Orlando. Johnson’s schedule included campaign stops at nearby Colonial Plaza, but the overnight stay carried its own weight. Just months earlier, this same hotel had been tangled up in ugly fights over racial segregation. Now the president who had just signed the Civil Rights Act of 1964 was sleeping under its roof. If that’s not a plot twist, nothing is.
The Baseball Chapter Nobody’s Proud Of
Here’s where the story gets uncomfortable, because it should. When the Washington Senators moved their spring training headquarters from the Langford Hotel in Winter Park to the Cherry Plaza in 1959, and later when the franchise became the Minnesota Twins in 1961, the team set up shop in the lakefront tower. Sounds great, right? Except the Cherry Plaza didn’t admit Black guests.
So white players and staff got the Cherry Plaza. Black players were sent to the Sadler Hotel, a Black-owned establishment on West Church Street. It was Jim Crow Florida doing what Jim Crow Florida did, right in the middle of America’s pastime.
Civil rights groups, students, and state officials pushed back hard. Boycotts were threatened. Public pressure mounted. And finally, in March 1964, the Twins ended their segregated housing arrangements and moved to integrated accommodations for spring training. It took way too long. But the Cherry Plaza’s role in that fight makes it part of one of the closing chapters of legally sanctioned segregation in professional baseball’s spring operations, a chapter worth remembering precisely because it’s not comfortable.
Walt Disney Drops the Biggest Bombshell in Orlando History at the Cherry Plaza Hotel
OK, if you only remember one thing about the Cherry Plaza Hotel, let it be this.
It was mid-November 1965 when Walt Disney, alongside his brother Roy and Florida Governor Haydon Burns, stepped into the Egyptian Room to face a crowd of eager reporters. For months, somebody had been secretly buying up thousands of acres of Central Florida land under the mysterious codename “Project X.” Rumors were flying. Reporters were digging. And now, in this ballroom inside a converted apartment building on Lake Eola, the truth finally came out.
Walt Disney stepped up to the podium and described what he called “a new world of pleasure, entertainment and economic development” for Central Florida. He promised the "Florida Project" would be bigger and more ambitious than Disneyland. He said it would employ thousands. The room full of reporters understood immediately: Orlando was about to become a very, very different place.
Here’s the kicker, that press conference was the only public appearance Walt Disney ever made in Orlando. He died just over a year later, in December 1966, long before Walt Disney World opened its gates in 1971. But that single afternoon in the Egyptian Room lit the fuse for everything: the attractions corridor along I-4, the tourism explosion, the international airport, the sprawl, and the whole wild ride that turned a mid-sized Southern city into one of the most visited destinations on the planet.
And where did it all start? In a ballroom that a radio station owner built inside a lakeside apartment tower. You truly cannot make this stuff up.
Pool Parties, Danny Thomas, and a Restaurant War with a Church
Not everything at the Cherry Plaza was history-book serious. Through the 1960s and 1970s, this was simply the place where Orlando went to let loose. The Egyptian Room and other public spaces hosted a nonstop parade of community banquets, dances, and receptions. Ask any longtime Orlando resident about the Cherry Plaza and there’s a decent chance they’ll mention the pool parties first, or the late nights in the Bamboo Room, which was apparently exactly as fun as a nightclub called the Bamboo Room sounds.
In 1966, entertainer Danny Thomas, who was then involved with the newly formed Miami Dolphins, threw a reception at the hotel to whip up excitement for Florida’s brand-new pro football franchise. Because when you needed to get people hyped about something in 1960s Orlando, you booked the Cherry Plaza.
Down on the ground floor overlooking the lake, the Columbia Restaurant, an outpost of the famous Tampa original, set up shop in the early 1970s. It was a perfect lakeside dining spot until it shut down after a dispute over liquor sales with a neighboring church (yes, really). Later, the same space became Lee Rose’s Lee’s Lakeside, a beloved fine-dining restaurant that served guests with a view of Lake Eola from the 1980s all the way until 2005, outlasting the hotel itself by years. Lee’s Lakeside was apparently the kind of place people still get misty-eyed about.
Full Circle: The Hotel That Went Back to Being an Apartment Building
Nothing lasts forever, especially a downtown hotel competing with the newer motor inns and mega-resorts sprouting up closer to I-4 and the attractions corridor. As Orlando’s center of tourism gravity drifted westward, the Cherry Plaza gradually faded from the spotlight. By the late 20th century, the property was converted back into apartments, completing the most satisfying narrative loop in Orlando real estate history. Born as apartments, died as apartments.
Today it goes by MAA Parkside, sitting on the south side of Lake Eola with a parking garage on South Osceola Avenue. It looks like a modest mid-century tower surrounded by flashier high-rise condos that arrived during downtown Orlando’s residential boom. But in the 1990s, before all those shiny neighbors showed up, the building had a reputation as a “funky” and eclectic spot to live, drawing residents with its reasonable rents and the kind of prime park-front location money usually can’t buy.
Why the Cherry Plaza Hotel Still Matters (Even If You Walk Right Past It)
Go walk around Lake Eola today. You’ll pass the old Cherry Plaza without blinking. No velvet ropes, no Egyptian Room, no Bamboo Room bumping on a Saturday night. Just a quiet apartment building minding its own business.
But packed inside those nine stories is basically a greatest-hits album of Orlando’s most dramatic decades: the post-war swagger of modern high-rise living, the mid-century glamour of convention-hotel culture, the painful reckoning with racial segregation in professional sports, a presidential sleepover, and, oh yeah, the single press conference that launched Orlando into the global stratosphere.
The Cherry Plaza Hotel proves that the most important places in a city’s story aren’t always the ones with the biggest signs out front. Sometimes they’re the quiet buildings on the lakeshore, hiding decades of wild history behind a very ordinary-looking front door, just waiting for someone to ask, “Hey, what happened in there?”
Now you know.
👉 I hope you love reading Orlando history as much as I like writing it. Get more Orlando history love, right here!
Sources:
https://orlandoretro.com/2013/08/08/the-intriguing-history-of-the-cherry-plaza-hotel-part-1/
https://orlandoretro.com/2013/08/31/one-last-stop-at-the-cherry-plaza-hotel/
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https://orlandoretro.com/2013/08/25/the-intriguing-history-of-the-cherry-plaza-hotel-part-2/
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