“This used to be a trailer park. People would drive their RVs — from all corners of the U.S. — and camp here,” says Cynthia Costa, general manager of Bungalows Key Largo, an adults-only, all-inclusive resort in Florida’s Key Largo. “There were no trees, it was all quite barren.”
Looking at the tiny white houses framed in pink bougainvillea and the connecting sandy lanes shrouded in palms, giant elephant ears, and lush banana trees, it’s hard to imagine the property ever being barren (owner Jerry Johnson has reportedly invested millions in landscaping). And yet, no-frills RV parks and ramshackle roadside stands spilling with oranges and lemons is exactly how I remember the Florida Keys. Numerous times I have made my way through this 120-mile spec of sea meets land — visiting “Flipper,” the bottle-nosed dolphin that lived at Santini’s Porpoise School in Marathon (now the Dolphin Research Center), taste-testing key lime pie, taking in the extraordinary gin-clear water views of Bahia Honda State Park. And always staying in Key West because it was home to the only luxurious accommodations. And Hemingway polydactyl cats.
But this visit (after many years), I’ve expanded my stay-over territory to the Upper Keys to include two of the newest luxury hot spots: Bungalows Key Largo and The Islands of Islamorada, a gated villa community.
Bungalows Key Largo: Dripping in Bougainvillea
Driving in from Miami, past the swampy mangroves of Florida Bay, fishing marinas, Starbucks, and Win-Dixies, I’m unprepared for the beauty awaiting behind the Bungalows’ unassuming gate. After ushering us onto a Tiffany blue golf cart, our host pushes open the entrance to reveal sandy roads lined with white bungalows. Johnson personally designed each of the 135 bungalows (some set in the sand with water views, others hidden deeply in the foliage).
Regardless of location, each tiny house comes with a front porch adorned with ceiling fan, Adirondack chairs, and matching pair of robin’s-egg blue bicycles, which we spontaneously ride to the zen (quiet) pool, spa, gym, and even to dinner. Interiors, with king beds and sitting areas, are neutral in palette — cream on whites and taupes — while an enclosed private yard offers an expansive wooden deck area, outdoor rain shower, and deep-soaking tub, which I dip into nightly and stargaze.
As the closest Key to Miami (only 65 miles), Key Largo is a magnet for the south Florida set looking to escape for a quick romantic weekend or leisurely few days alone. Many Miamians own second homes here and commute between. But for those who don’t, the adults-only Bungalows offers a much-needed (and welcome) reprieve. Once checked in, most couples (like us) never leave.
In our bougainvillea-draped bungalow, we easily find our rhythm. Morning coffee on the porch or private deck. For breakfast, we bike along sandy lanes to the Mediterranean-infused Fish Tales (restaurant), inspired by Johnson’s personal love for Il Riccio in Capri. The rest of the day is at whim. Kayaking, paddleboarding, and water trikes are popular pastimes, as are snorkeling, swimming, or simply hiding under a wispy beach cabana sipping the resort’s signature Tiki Tai, a fusion of coconut rum, amaretto, orange and pineapple juices.
Spa is also a must. And here, a reminder that quantity (just five treatment rooms) does not supersede quality. Following time in the steam, sauna, and Himalayan salt room, I follow Jose, my therapist, through a forest of green bamboo and stepping stones to an outdoor tiki hut for an anything-but-simple massage.
“I could spend the entire hour on this shoulder blade alone,” he tells me, pressing his forearm (versus hands) into my knotted back. Moving through the treatment, I feel muscles snapping back into place, as he narrates extraordinarily accurate findings. “You sleep on your right side,” he says, a statement not a question. (I do). “Try sleeping on your back, it’s better for your head and neck. I also suggest you try rolfing” (a therapy using deep-tissue manipulation to improve posture and reduce pain). Walking me back into the relaxation area, he quickly pulls his phone from his pocket. “Where do you live,” he inquires, and within seconds, locates a rolfing master, who resides in the next town over.
Dinners are equally special. Fish and seafood are served on colorful Italian plates at Fish Tales; Mexican is the theme at romantic, toes-in-the-sand Sea Señor. But for exclusive fine dining, head first to Hemingway Bar, adorned with black-and-white photos of the famous author for crafted cocktails (try the lavender cloud). Follow with dinner at Bogie & Bacall’s, beloved for its old Key West vibe and house specialties like grilled lobster tail, cowboy ribeye steak, and creamy white risotto. (Dinner is included for those staying four nights; otherwise is $300 per couple).
The Islands of Islamorada: An All-Villa Resort
There’s no restaurant at this gated villa resort in Islamorada (a.k.a. the sports fishing capital of the world) — aside from the poolside tiki bar serving cocktails, Champagne, and quick lunches of fish tacos and burgers. But each of The Islands of Islamorada’s 22 three-story, private villas comes with a full-scale gourmet kitchen, four bedrooms, four-and-a-half bathrooms, multiple terraces and patios, ocean views, a two-car garage (with charging station), laundry, and fabulous artwork — much of it ocean inspired — by accomplished local artists. We loved the up-close swaying palm tree in the stairwell of our airy villa (#3), and what could be cliche but isn’t — the flock of pink flamingos hanging near our bed.
Private chefs, massage therapists, yoga instructors, boat captains, fishing guides, watersports handlers, and on-demand coconut crackers (who shimmy up trees and machete fresh coconuts) are always on standby.
Spanning seven acres, this oceanfront villa resort (like Bungalows) is built on the site of a former RV trailer park. The property was originally purchased in 2004 by the Frisbie Group, a private, Palm Beach-based real estate investment firm founded by three brothers, and known for properties including Via Flagler by The Breakers and South Flagler House in Palm Beach, and Harborview Nantucket, Massachusetts, among others. The family spent years rezoning and master planning the Islamorada site which came with a mom-and-pop hotel called Ocean House that sustained major damage from hurricane Irma (in 2017). The new incarnation of that structure now houses eight oceanfront suites, the tiki bar, and pool.
“It’s basically the same layout [as the old Ocean House] but much more luxurious,” says Marissa Krohn, owner and guest services manager at The Islands. On the neighboring lot, a former oceanfront RV trailer park community, the Frisbies built the private villa residences.
The Islands Islamorada officially opened in 2020, and in July 2024, ownership changed to the Wills Companies (also family owned), which has kept the resort and concept completely intact, but with one major caveat: the option to purchase. The villas start at $4.95M.
“Both the Frisbee and the Wills families have preserved the spirit of Islamorada and core reason visitors have always wanted to come here,” says Krohn. “The old timers didn’t care about luxury. They came for the water, the beach, the laidback lifestyle, and, of course, the fishing. Today’s visitors want all of those same things: peace, tranquility, and a place to unwind. But they also care about luxury. And the owners have really brought that element.”
The gated culture, for starters, brings a feeling of safety, especially for solo travelers; the mature landscaping — towering coconut palms, lush croton, hibiscus, and blooming orchids — a sense of beauty. With two pools, a hot tub, fire pit, two pickleball courts, and acres of shoreline, there is also ample space.
While families (children and dogs are welcome) often rent out the villas, the resort never — even at full capacity — feels crowded. A private marina enables guests to bring their own boats; fishermen can troll the nearby waters with a captain or fish for tarpon right off the dock; a driving range enables golfers to hit biodegradable balls (filled with fish food) straight into the ocean. And there’s the simple luxury of relaxing under a waving palm tree or wooden rope swing — fresh coconut water in hand — watching pelicans dive bomb for fish.
Getting out onto the water (beyond sport fishing) is a must here and we answer the sea-siren call with a private sunset cruise. Picking us up at our villa, Captain Rob heads first to Venetian Shores (on the bayside) where streets and lagoons come with names like Stromboli and Palermo, before moving to the island’s most exclusive gated neighborhood, Pen Key Rod & Reel Club, known for its unique architecture.
“Long before there were infinity pools, Islamorada had infinity homes,” says Captain Rob, slowing the boat to show us a one-level house — water views from every room — that seemingly blends into the bay. He explains that the oldest homes on the island were built between 1937 and 1941 because “the 1935 hurricane wiped everything out.” And when I ask him about manatees, he quietly glides the boat through glass-like waters to a secret cove in the mangroves where the giant, lumbering sea cows are known to hide.
Captain’s final share with us comes in the orange-pink-red sunset, as spectacular as I’ve ever seen. Slowing the boat to a complete stop, he pours us glasses of bubbly and, clinking (boat-safe) glasses, we watch the giant fireball sink into the blue-purple water. Heading back to the resort, the sky fading into night, he points out one final nugget: the island’s last remaining trailer park.
“Islamorada used to be filled with run-down mobile homes and [RV] trailer parks. Now we have only one left.” He motions to the lone park near Coral Bay Marina, which Bloodline fans will immediately recognize as “Ken’s Marina.” The Netflix series was filmed here.
Continuing through the placid waters, past more stunning homes to our own multi-million-dollar villa, the transformation is evident. This is not the Florida Keys I remember. Or my parents’ Florida Keys before me. From the upper (Key Largo and Islamorada) to the lower (all points south of the Seven Mile Bridge), the Keys — alongside their still-quirky seashell souvenir shops and mom-and-pop restaurants — are embracing luxury.
And I, for one, am all in.
Feature image, courtesy of The Islands of Islamorada
