Opened in 1946 by Carl Twitchell — "Cheeca" being the elision of his wife Olive Cinque-Mars's first names — this 27-acre oceanfront estate in Islamorada has been the Keys' uncrowned grand resort for nearly eighty years, hosting four U.S. presidents and the founding banquet of the Florida Keys National Marine Sanctuary.
"The Queen of the Florida Keys, opened 1946 — the oldest grand resort in the Keys and still the only one where four generations book the same week each March."
Cheeca Lodge opened in 1946 as a private fishing club for Cleveland industrialist Carl Twitchell and his wife Olive Cinque-Mars — "Cheeca" being the contraction of their first names — and was opened to the public in 1960. The property occupies 27 acres of oceanfront at Mile Marker 82 in Upper Matecumbe Key, with 1,200 feet of private Atlantic shoreline, a 525-foot fishing pier (the only private pier of this length in the Keys), and a nine-hole executive golf course laid out in 1957. Three U.S. presidents — George H.W. Bush, Bill Clinton, and Jimmy Carter — have stayed; Bush Sr. signed the executive order establishing the Florida Keys National Marine Sanctuary at Cheeca in 1990, an event still memorialized in the lobby.
The lodge was substantially destroyed by Hurricane Wilma in 2005 and rebuilt; in 2008 a New Year's Eve fire took the main building, which was reconstructed and reopened in 2010 with a careful preservation of the 1946 Bermuda-shingle aesthetic in updated five-star envelopes. The current owners — RAIT/Pebblebrook — completed the most recent property-wide refresh in 2023, replacing every guest-room textile and reworking the Atlantic's End restaurant and the Spa at Cheeca. The result is a property that holds its 1946 silhouette and palette while delivering contemporary five-star bones.
The 214 rooms and suites are split across the Main Lodge (renovated 2010, the historic envelope), Beachfront Bungalows (low-density two-story buildings on the Atlantic side), and the Casitas (the resort's largest residential-style units, ideal for multi-generational families). Beachfront Bungalow Suites are the standard upgrade booking — directly on the Atlantic, oversized terraces, the Keys' best sunrise positions. The Presidential Suite occupies the top corner of the Main Lodge with the best view on the property. The spa is the largest in the Upper Keys; the kids' club, Camp Cheeca, has been continuously operated since 1968 and is the deepest-tenured kids' program in the Keys.
Atlantic's End, the resort's flagship restaurant, runs a Florida-Caribbean menu under chef Ron Pence, focused on Keys-sourced seafood with an emphasis on local hogfish, yellowtail snapper, and stone crab in season. Nikai is the on-property Japanese-Peruvian option; Limoncello serves Italian poolside. The lodge's catch-and-release fishing program is operated in partnership with Bud N' Mary's Marina across the highway, and Cheeca's pier remains one of the strongest light-tackle bonefishing platforms anywhere in the western Atlantic. By any honest measure Cheeca is the most consequential historic hotel in the Keys.
For multi-generational Florida Keys family weeks Cheeca is the obvious answer. Camp Cheeca — the Keys' oldest kids' club, operating continuously since 1968 — covers ages 5–12 with a structured program of marine biology, kayaking, and beach activities. The Casita category provides residential-scale accommodations for grandparents-plus-grandkids configurations; the nine-hole golf course, three pools, and 525-foot pier give adolescents a credible day's schedule.
An Islamorada anniversary at Cheeca can be calibrated across the property's three accommodation types — a Beachfront Bungalow Suite for the weekend version, the Presidential Suite in the Main Lodge for the milestone year. Atlantic's End at dinner is the flagship room; the Spa at Cheeca offers Sothys couples treatments; and the resort's 1946 main lodge gives the celebration a sense of historical scale that the Keys' newer properties cannot match.
For honeymoons the Beachfront Bungalow Suites are the booking — directly on the Atlantic with the property's best sunrise positions and the largest private terraces. The 525-foot pier is a working sunrise breakfast spot; the spa's three couples suites are private rooms with outdoor showers. The combination of Cheeca's historic envelope, the genuine 27-acre scale, and the relative scarcity of day-trippers makes it materially quieter than its Marathon and Key Largo peers.
81801 Overseas Highway
Islamorada, FL 33036
United States
Mile Marker reference: Mile Marker 82, Islamorada; Miami International Airport approximately 1–2 hours by car
214 rooms and suites
From $277/night
WiFi: complimentary, high-speed throughout
5-Star
Check-in: 4:00 PM
Check-out: 11:00 AM
Founded 1946; rebuilt 2010 after fire; property refresh completed 2023
Atlantic's End restaurant · Nikai · Limoncello · Spa at Cheeca · Camp Cheeca kids' club (since 1968) · Nine-hole golf course · 525-foot fishing pier · Three pools · 1,200 ft Atlantic shoreline
From $277/night with a $37.97 resort fee. Beachfront Bungalow Suites book 3–4 months ahead for winter weekends; Camp Cheeca summer weeks book 4–6 months out; tarpon season (mid-March through June) commands a 30–50% premium.
Book This Hotel →The only adults-only, no-passport, all-inclusive resort in the United States
The Keys property that single-handedly invented the modern barefoot-luxury cottage category
The Keys' newest purpose-built grand resort