Florida Keys, FloridaOld Town
Winslow's Bungalows
Restored cottage compound
Old Town Florida Keys, Florida
Opened
2020
Price
$$$
Rated for
Design Heritage LocalOutside the door
The house
Key West Historic Inns CollectionRestored cottage compound
A cluster of restored nineteenth-century cottages runs like a residential compound, connected by garden paths and three swimming pools.
“The place just oozes a hip vibe with its retro-chic decor and intimate setting that makes you feel like you have the run of the place.”
What it’s good at
Notable
Powerstrip Studio brought mid-century furniture and graphic palm prints to restored Victorian cottages.
Notable
Nineteenth-century Conch houses and Victorian cottages preserved across a lush Key West block.
What they say
Michelin Selected
Michelin
Also in Condé Nast Traveler.
Winslow’s Bungalows, named for the maritime painter Winslow Homer, spans several houses in a variety of styles (as well as three swimming pools) in the historic district of Key West.
Right in the middle
Well-located: walkable to some things, a short ride to more.
The Ernest Hemingway Home and lively Duval Street sit three blocks away through residential Old Town.
1 of 8
The rooms
Airy guest rooms feel like private residences across the historic houses, with louvered shutters and deep soaking bathtubs.
The pools
Bring a swimsuit.
Wooden sun decks and fringed umbrellas surround the pools, tucked among palm trees and tropical gardens.
The Bungalow Bar
The open-air poolside pavilion sits under rope pendant lights, serving cocktails and mahi tostadas beside the water.
How it began
Painter Winslow Homer wintered in Key West around the turn of the century, lending his name to the property.
Florida Keys
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The app
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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.