Winslow's Bungalows

Embark on the ultimate Key West adventure at this elegant home-away-from-home on Florida’s south coast

Eclectic, relaxed, and easy chic, Winslow’s Bungalows reflect the spirit of Key West at every turn. A thoughtful blend of historic Victorian architecture and modern styling creates a stay that feels both characterful and current. Located in the heart of Old Town, this curated collection of self-contained bungalows serves as your ideal launchpad to explore this colourful pocket of island paradise.

Wind your way through leafy walkways to your front porch and step into beautifully appointed interiors designed for comfort and ease. Wake up to views of the Basilica of St. Mary Star of the Sea from the King Suite with Sofa Bed, or stay in the former home of historian Colonel Walter Maloney. Or stay close to nature in the Treehouse Suite where a secluded balcony among the treetops is accompanied by tropical birdsong.

Key West is a hub for bohemian adventure – with a pleasing balance of history, beaches, restaurants and nightlife. The 19th Century Fort Jefferson is just a boat (or seaplane) ride away at the Dry Tortugas National Park, where sea turtles swim and you can dive the Windjammer Wreck on Loggerhead Reef. Or explore the former residence of Ernest Hemingway and its famous six-toed cats.

Enjoy your stay!

85 Rooms | 3 Floors | 1 Restaurant |

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Historic Hotel

Honeymoon

Pool

Family Friendly

Our Hotel

Winslow's Bungalows
Winslow Exterior
Lobby
Lobby
Lobby
Key Lime - Bedroom
Bungalow - Exterior
Classic King
Winslow - Bedroom
Bathroom
Garden
Winslow - Exterior
Winslow's Bungalows
Winslow - Exterior
Winslow - Exterior
Winslow - Exterior
Winslow Mobility - Bedroom
Patio
Winslet - Patio
Winslet - Patio
Two Queen - Bedroom
King Suite with Soaking Tub - Bedroom
Soaking Tub
King Suite with Soaking Tub - Bathroom
King Suite with Sofa Bed - Bedroom
King Suite with Sofa Bed - Bedroom
Bathroom
Annex - Bedroom
Annex - Bedroom
Annex Mobility - Bedroom
Treehouse Suite - Bedroom
Treehouse Suite - Bedroom
Treehouse Suite - Bathroom
Treehouse Suite - Living Area
Treehouse Suite - Balcony
Bungalow Bar
Bungalow Bar
Picnic Area
Pool
Pool
Pool
Pool
Pool
Trail
Trail
Trail
Trail
Trail
Trail
Trail
Winslow Facade
Winslow's Bungalows - Aerial

Our rooms

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Treehouse Suite

Sleeps 2

King

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Ratings

SLH Club Reviews

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Winslow's Bungalows, United States

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Key Features

Restaurant

Bar

Air conditioning

Pet Friendly

All Hotel Features and Services

Concierge desk
Doctor on call
Parking
On-Site parking
Wakeup service
Pool
Wedding services
Accessible parking
24-hour security

All Hotel Features and Services

Concierge desk
Doctor on call
Parking
On-Site parking
Wakeup service
Pool
Wedding services
Accessible parking
24-hour security
Air conditioning
Bar
Family friendly
Pet Friendly
Fire safety compliant
Full service housekeeping
24-hour front desk
Security
Restaurant
Wi-Fi in public areas
Pool
Outdoor pool

Food And Drinks

Greet the morning with fresh croissants and coffee followed by a full continental breakfast. Or explore the local café scene on nearby Duval Street, with curated restaurant recommendations from the hotel staff for daytime and evening meals. Between meals, three outdoor pools and poolside refreshers served each afternoon mean you can always stay cool as you ease into Floridian life.

Bungalow Bar

Served Meals: Breakfast, Lunch Bungalow Bar is a tropical poolside bar with specialty bites served for lunch daily - a signature cocktail menu served all day and where daily breakfast is offered during the week. On one side a relaxing pool and on the other - an indoor self-serve area and covered outdoor seating. Brunch is served on the weekends and live music and liquor tastings are offered. Retreat into a lush and welcoming oasis of poolside bites specialty cocktails - anytime bubbles and cold beer.