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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.

Lobby at Winslow’s Bungalows

Passage to Bohemian Beauty

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.


Winslow's Bungalows

(Previously Chelsea House + Key Lime Inn)

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

Perfect for: Families, groups and couples

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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The pool at Winslow’s Bungalows
King bed with sofa at the foot of the bed and windows pictured.
Lobby at Winslow’s Bungalows

Ridley House

(Previously Cypress House)

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

Perfect for: Honeymooners and couples

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

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Scenic Pool
Suite at Ridley’s

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: groups and travelers looking to spend time in the art district

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

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Pool at Ella’s Cottages
Accommodations at Ella’s Cottages
exterior walk way to our ella’s cottages king guestroom with outdoor private seating
Ella’s Servery

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: Groups and travelers looking to visit historic Key West sites

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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Scenic Pool
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Isabel’s Bar at Lighthouse Hotel

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: travelers looking for activities, sightseeing and water adventures

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

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fitch lodge king bed centered with white sheets and pastel accents
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.