By  Mike Miller  Updated December 3, 2022

Kenansville is a spot on US-441 about halfway between Yeehaw Junction and Holopaw. Most travelers whiz through without knowing anything about the history of the place.

Heartbreak Hotel, Kenansville, 2003Heartbreak Hotel, Kenansville, 2003

It's name ties into the history of one of Florida's iconic developers, Henry Morrison Flagler.  Henry is the man who really opened up Florida to tourism.

After making a fortune as John D. Rockefeller's partner in Standard Oil, he retired and focused his business skills on ventures in the Sunshine State.

His projects and invested capital in the 1880's through 1912 transformed Florida forever.

Map of FEC RR Kissimmee Valley BranchMap of FEC RR Kissimmee Valley Branch

He started with big hotels in St. Augustine, bought a railroad, and then extended his railroad and hotel empire down the east coast of Florida until he finally made it all the way to Key West.

The Overseas Highway follows the roadbed of Flagler's Florida East Coast Railway.

Toward the end of his life he also began construction on a branch of the railroad that ran from near New Smyrna Beach all the way down to Okeechobee.

Henry FlaglerHenry Flagler
Mary Lily KenanMary Lily Kenan

Flagler's first wife had died, and his second wife had been confined to an institution for mental illness for many years. You might say he had been unlucky in love.

At last, however, he fell in love with a lovely young lady named Mary Lily Kenan, and wanted to marry her.

Kenansville First State BankKenansville First State Bank

In those days, it was almost impossible to get a divorce in Florida.

Flagler convinced the Florida Legislature to pass a bill allowing a spouse to get a divorce if their mate was mentally ill.

It was considered a scandal at the time, but Henry Flagler got divorced. 

He and Mary Lily got married and lived happily ever after in Whitehall, their Palm Beach mansion.

Florida East Coast Railway Depot Circa 1910Florida East Coast Railway Depot Circa 1910

The Kissimmee Valley branch of Flagler's railroad followed the route that is now US-441. 

Some of the whistle stops along the way included Holopaw, Illahaw, Nittaw, Apoxsee, Hilo, Efaw, and Opal. 

Another of the little communities along the way offered to name their town Flagler after him if he ran the railroad through it.

Flagler declined the name offer, but asked them to name it after his wife instead.  And thus was born Kenansville.

Heartbreak Hotel Silverprint by Lloyd BehrendtHeartbreak Hotel Silverprint by Lloyd Behrendt

Most Floridians know the town as the home of the Heartbreak Hotel. Rumor has it that Elvis stayed there and named his song after the place.

The truth is the owner of the hotel liked the song and named his hotel after it.

The silverprint painting of the hotel is available from the artist, Lloyd Behrendt on his Facebook page. 


Kenansville Community Center and Park 
1178 South Canoe Creek Road, Kenansville, FL 34739. (407) 436-8001 

Immerse yourself in the local culture by visiting the Kenansville Community Center, a hub of community events and activities. Check the schedule for local fairs, farmers' markets, and live performances.

This is the perfect opportunity to mingle with locals, support small businesses, and get a taste of Kenansville's tight-knit community spirit.

From craft shows to live music, there's always something happening at this lively center that offers a true slice of Florida hospitality. 

Wild Florida Drive-Thru Safari Park
3301 Lake Cypress Rd, Kenansville, FL 34739. (407) 957-3135 

Embark on a wild adventure at Wild Florida, a wildlife park dedicated to preserving Florida's diverse ecosystems. Our highlight? The airboat tours that take you through the headwaters of the Everglades, showcasing native wildlife like alligators, eagles, and more.

The park also features animal encounters, allowing you to get up close and personal with fascinating creatures. Whether you're exploring the park's exhibits or enjoying a hands-on animal encounter, Wild Florida promises a memorable and educational experience for visitors of all ages. 

Kenansville Cemetery 
100 Lake Marian Rd, Kenansville, FL 34739 

For a step back in time, pay a visit to the Kenansville Cemetery, a historic site that whispers tales of the town's past. Wander through the gravestones, some dating back over a century, and reflect on the stories of the pioneers and settlers who shaped Kenansville.

It's a serene and contemplative stop, offering a quiet moment to pay respects and connect with the rich history that lays beneath the moss-covered oaks. 


Jun 14, 2020
Cow Palace
by: Tom

I hauled fruit back to Orlando for one season from a friend's grove down the 10 mile grade and ate at the Cow Palace every chance I got. Also hunted in the area for several years and always enjoyed my meals at the Cow Palace.

Sep 18, 2019
Bank Building
by: Jim Haynes

I owned the Bank Building in the early 1970s until 1974. I had a lot of dreams, but they never panned out. A lot of history. Maybe someday someone will put it out.

Thanks Jim Haynes

Sep 23, 2018
Love looking at the old home place
by: Marla Hughes

I was trying to find a photo that included the house I grew up in that was just past the Old Bank Building and came across this site.

I see Diane, my old boss from the Cow Palace found you, too!

Oct 16, 2017
Cow Palace
by: Diana Cox

My husband & I owned the Cow Palace. We were the only owners to have a beer & wine license. We were also the cooks. It was such a surprise to read about our restaurant in this article. We still live in the Kenansville community & we are now customers at the restaurant which is now Griffis Cafe.

Oct 16, 2017
My father
by: Sherman Drawdy

My father Willie A Drawdy was born in Kenensville in 1891 to Amanda Francis Green Drawdy and Willie Arthur Drawdy. Does anyone have any information on either family? I am 75 and looking for information on my family.

Mar 27, 2017
Cow Palace
by: Anonymous

My hunting companions and I would eat dinner regularly at the Cow Palace and drink Heineken beers for $2 a piece. We would call ahead during the week just to make sure they stocked up so they wouldn't run out. Best Steaks east of Bern's. Fond memories.

Jun 14, 2016
Kebabs like School
by: Anonymous

I was lucky enough to have gone to school while it was still open. I have nothing but fond memories and had the best teachers.

Jun 14, 2016
Childhood memories
by: Michelle Little (Campbell)

I remember passing this place everyday to go to school in St.Cloud from Yeehaw. There was a man named Mr.Webb that wrote a book many years ago and he has written about this place as well. He was crippled but had a van customized that he could drive and he would pick us up and take us to church. I have a lot of family buried in Kenansville as well. Thanks for the article!

Jun 14, 2016

The Sale
by: K Marquette

Passed by there just last week, June 2016 and the building and land is for sale. Looks like it would be a nice B&B with some great fishing on the lakes that are around that area.

Nov 01, 2015
The view out my window.
by: Marla Hughes

That picture basically mirrors the view out my side windows. I grew up across the street and down a lot from the Heartbreak. It's had it's ups and downs through the years, as has Kenansville. Thanks for the nicely done article. 


Thanks for the kind words, Marla. You probably know how rare a person you are: someone who grew up in Kenansville, Florida. Not many people in the world can say that.

Sep 07, 2014
Hotel is for sale
by: Anonymous

The building has been For Sale for several years and recently the gift shop has closed.


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