Florida Keys, FloridaIslamorada
Cheeca Lodge & Spa
Sporting oceanfront estate
Islamorada Florida Keys, Florida
Renovated
2022
Price
$$$
Rated for
Resort Classic HeritageOutside the door
Sporting oceanfront estate
The estate runs like an unhurried sporting club, where private beachfront lounging alternates with backcountry boat charters and tennis.
“Cheeca Lodge manages to be upscale and relaxed at the same time. This duality is perhaps best embodied in Cheeca’s flagship restaurant Atlantic’s Edge.”
What it’s good at
Notable
Angling traditions and presidential fishing tournaments have anchored the grounds since 1946.
Listed
An on-site nineteenth-century pioneer cemetery preserves early Upper Keys settler history.
What they say
Also in Condé Nast Traveler and AFAR.
The rooms and suites have just the right amount of Floridian flair—think palm leaf fans, rattan furnishings, and a few bright colors.
Tucked away
A place apart: the property is the destination.
Pierre's sits directly across the highway for sunset drinks over Florida Bay. Down the road, marina docks let visitors hand-feed giant tarpon.
1 of 5
The rooms
Premier oceanfront suites open onto private lanais with deep outdoor soaking tubs overlooking the water.
The pools
Bring a swimsuit.
Three heated pools include a zero-entry pool overlooking the water and a dedicated lap pool lined with cabanas.
The spa
The 5,700-square-foot spa houses steam rooms, a Vichy hydrotherapy room, and an outdoor deck with cascading waterfalls.
At the table
Atlantic's Edge serves local seafood overlooking the water, and the thatched Tiki Bar pours cocktails beside the beach.
How it began
Heiress Cynthia Twitchell gave the property its name in 1962, combining her nickname Chee with her husband Carl.
Florida Keys
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Our shorthand
How we rate hotels.
The medals
Gold
Extremely rare. Sets the global standard.
Silver
Brilliant execution. And we’re picky.
Bronze
They did this well. You’ll notice.
Listed
A defining trait. Makes the hotel what it is.
The eight vibes
Design
Built around a vision. Even the door handles have a designer.
Luxe
Cared for at every turn. The bath is drawn before you ask.
Local
It could only be here. You wake up knowing where you are.
Social
Where the city goes out. The bar is full and the night is young.
Heritage
A building with a story. Once a palace, a monastery, a station.
Wellness
You leave feeling new. Rest, sweat, soak and sleep like a stone.
Classic
The city grew up with it. Same rituals, same regulars, same bar.
Resort
A world of its own. Something to do from breakfast to nightcap.
The scene
Lively
Where things happen: restaurants, shops, people.
Central
Well-located: walkable to some things, a short ride to more.
Quiet
Away from the crowds. Getting around takes intention.
Secluded
A place apart: the property is the destination.