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Discover Our Historic Key West Hotels

Vibrant Key West Boutique Hotels

The pool at Winslow’s Bungalows

Discover Our Historic Key West Hotels

Vibrant Key West Boutique Hotels

entry walkway to our winslow’s bungalows king guest room with seating and plush gardening providing privacy.

Discover Our Historic Key West Hotels

Vibrant Key West Boutique Hotels

Lobby at Winslow’s Bungalows

Discover Our Historic Key West Hotels

Vibrant Key West Boutique Hotels

Passage to Bohemian Beauty

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Here in the heart of Old Town Key West, a collection of private sanctuaries invites you to unwind, let loose and embrace the carefree spirit of the Keys. Our five hotels offer a total of 219 guestrooms and suites throughout a medley historic architectural gems, each with its own personality. Yet they’re all united in layered bohemian style—from elegant summer cane beds and antique European armoires to the fresh white palette that pops with tropical tints. The easy-going ambience extends outdoors to winding walkways, hidden nooks, inviting pools and our signature vintage Moke parked outside. Are you feeling the Key West warmth already? Just wait till you get here.


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The pool at Winslow’s Bungalows
Winslow’s Bungalows exterior
Winslow’s Bungalows restaurant
Winslow’s Bungalows room

Winslow's Bungalows

(Previously Chelsea House / Key Lime Inn)

Lush Garden Retreat With Playful Amenities

Three pools, winding brick walkways and tropical greenery woo guests to an enchanting Key West experience.

Perfect for: All Travelers

Walk to: Duval Street, The Basilica of St. Mary Star of the Sea, Southernmost Point Buoy, Lighthouse Museum and Hemingway House and Better than Sex Dessert Restaurant

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Ridley House
Ridley House
Ridley House

Ridley House

(Previously Cypress House)

Once the estate of a prosperous industrialist, adult-exclusive retreat Ridley House charms guests today with Bahamian architecture and high-end luxe.

Perfect for: Adult Retreats, Couples

Walk to: Sloppy Joe’s Bar, Mallory Square, Key West Historic Seaport, Key West Ferry Terminal and Waterfront Brewery

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Pool at Ella’s Cottages
Ella’s Cottages
Ella’s Cottages
Ella’s Cottages

Ella's Cottages

(Previously Merlin Guest House)

Enjoy a front-porch seat to the lively Key West scene at this intimate retreat in the center of Old Town.

Perfect for: Couples, travelers seeking larger accommodations

Walk to: Duval Street and Bourbon Street Pub, Southernmost Point, Bahama Village, Lighthouse Museum and Hemingway House

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Lighthouse Hotel Pool
Isabel’s Bar at Lighthouse Hotel

Lighthouse Hotel

(Previously Lighthouse Court Hotel)

Lively social scene with a bustling bar meets iconic views of the Key West Lighthouse and Hemingway’s home.

Perfect for: Any size party

Walk to: Ernest Hemingway House and Museum, Key West Lighthouse and First Flight Island Restaurant and Brewery, Southernmost Point and Green Parrot Bar

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Fitch Lodge lodge room
Fitch Lodge facade
Fitch Lodge studio suite
Fitch Lodge Pool

Fitch Lodge

(Previously Albury Court)

Return from reef diving or deep-sea fishing to informal, bohemian conch-house lodging in a neighborhood setting.

Perfect for: Single and group travelers

Walk to: Waterfront Brewery, Key West Historic Seaport and ferry terminal

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bar

Events

See What's Happening in Key West

CALENDAR OF EVENTS

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Amenity Winslows Bungalows Lighthouse Hotel Ridley House Fitch Lodge Ella's Cottages
Pool 3 1 1 1 1
Pool Bar 1 1 - - -
Breakfast Included
Food and Beverage Pool Bites and Bungalow Bar Isabel's Bar - - -
Spacious Suites
King Bed
Two Queen Beds - -
Parking - -
Perfect for... All Travelers Any size party Adult Retreats, Couples Single and group travelers Couples, travelers seeking larger accommodations
Closest to... Duval Street and Southernmost Point Buoy Lighthouse Museum and Ernest Hemingway House Mallory Square and Key West Historic Seaport Key West Historic Seaport and Garrison Bight Marina Duval Street and Bourbon Street Pub
Adult Exclusive - - - -

all red brick exterior to the key west local museum

Eclectic Island Enchantment

Welcome to 4.2 square miles of free-to-be-you eclectic bliss trailing off the tip of Florida. Yes, it’s in the U.S., but Key West is another world. From tangerine sunsets to sword-swallowing stunt performers at Mallory Square, free-wheeling travelers will feel right at home in Key West.