Florida Keys, FloridaIslamorada
Islander Resort
Mid-century oceanfront compound
Islamorada Florida Keys, Florida
Renovated
2025
Price
$$$
Rated for
Resort Design LocalOutside the door
Mid-century oceanfront compound
The property spreads across 24 oceanfront acres in relaxed 1950s fashion, favoring lawn games and flip-flops over resort formality.
What it’s good at
Notable
Two oceanfront pools and a nine-hole putting course across twenty-four Atlantic acres.
Listed
Bungalows frame 1950s modernist lines alongside colorful contemporary artwork and open Atlantic views.
Listed
An on-site discovery museum chronicles Florida Keys history, coral reefs, and legendary wrecks.
What they say
Also in Condé Nast Traveler.
Low-key and laidback, this resort attracts a flip-flop-and-T-shirt-wearing kind of crowd. If you’re looking for posh, look elsewhere; but if you want comfortable accommodations that won’t soak you, the Islander fits the bill.
Tucked away
A place apart: the property is the destination.
Along Overseas Highway at Mile Marker 82, fronting twenty-four acres of Atlantic shoreline on Islamorada.
1 of 5
The rooms
Suites feature full kitchens, while low-rise bungalows lean into clean modernist lines, vibrant artwork, and private lanais.
The pools
Bring a swimsuit.
Slatted wooden cabanas line the beachfront Tides Pool, and the freshwater Oasis Pool rests under coconut palms.
The spa & gym
At the table
Drift on the Beach serves open-flame coastal cooking, and thatched bars pour rum cocktails right along the sand.
How it began
Chicago attorney Leo Samuels founded the property in 1951, crowned by a Space Age neon sign along the Overseas Highway.
Florida Keys
More like this
Little Palm Island
“Thatched bungalow islet”
Cheeca Lodge & Spa
“Sporting oceanfront estate”
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
“Oceanfront marina playground”
Baker's Cay Resort Key Largo, Curio Collection by Hilton
“Bayfront hammock resort”
Amara Cay Resort
“Modern rustic resort”
The Perry Hotel & Marina Key West
“Industrial boatyard lodge”
The Reach Key West, Curio Collection by Hilton
“Natural-sand beachfront resort”
Reefhouse Resort
“Key Largo dive resort”
The app
Like this one? There are so many more.
Swipe any city’s hotels and heart the ones you love. The app gets your taste.
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.