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Winslow's Bungalows - Key West Historic Inns rates, Key West

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Get current prices at Winslow's Bungalows - Key West Historic Inns. Set the traveler’s dates and guests; the results include current room prices and the customer’s Open hotel details link. Selecting a room or rate is optional.

#5 of 9 hotels in Old Town & Duval Street by Axel's take. Old Town & Duval Street is #1 of 6 places to stay in Key West. The best hotels in Old Town & Duval Street, ranked · Where to stay in Key West

Axel's take: 8.4/10

A strong Old Town pick for garden pools and character, not polished luxury. a historic 4-star bungalow-style inn in Old Town, scored for what it is.

Winslow’s is a historic 4-star bungalow-style inn whose appeal is its leafy setting rather than full-service luxury. We'd pick it for exploring Old Town on foot, then returning to three pools and a sociable poolside bar. Recent Expedia and Tripadvisor guests repeatedly praise the welcoming staff, well-kept grounds and generally clean rooms. Included continental breakfast is a useful extra, and Duval Street is only a few blocks away.

The catch is room selection: these historic buildings aren't uniform, and smaller rooms can feel tight. Tripadvisor guests also mention uneven maintenance, though recent feedback remains strongly positive overall. Check the exact room category rather than assuming every booking means a standalone cottage or private patio. A nightly amenity fee and limited, paid parking weaken the value. We'd skip it if spacious rooms and consistently polished finishes are priorities.

  • Best for: couples exploring Old Town; travelers who prefer historic character; pool-and-bar downtime

  • Watch out for: small rooms and variable layouts; uneven maintenance in historic buildings; amenity fee and limited paid parking

  • Location: Walkable Old Town setting a few blocks from Duval, without being directly on the main nightlife strip.

  • Rooms: Check category details carefully: size, building placement and private outdoor space vary.

  • Cleanliness: Strong overall feedback, with recent Expedia guests repeatedly describing clean rooms and maintained grounds.

  • Service: Friendly front-desk staff and bartenders are recurring strengths; occasional service lapses appear on Tripadvisor.

  • Amenities: Three pools, Bungalow Bar, continental breakfast, live music and on-property bicycle rentals.

  • Fees and surprises: Check whether the nightly amenity fee applies to your reservation; limited parking and pets cost extra.

Axel's opinion of Winslow's Bungalows - Key West Historic Inns, from the hotel's website and recent guest reviews. Sources: Hotel website · Tripadvisor · Expedia · Booking.com. Reviewed Oct 20, 2026.

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#5 of 9 hotels in Old Town & Duval Street by Axel's takeOld Town & Duval Street is #1 of 6 places to stay in Key West

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4-star hotel · Key West, United States

Hotels in Key West

Axel's take

a historic 4-star bungalow-style inn in Old Town

8.4/10

A strong Old Town pick for garden pools and character, not polished luxury.

Winslow’s is a historic 4-star bungalow-style inn whose appeal is its leafy setting rather than full-service luxury. We'd pick it for exploring Old Town on foot, then returning to three pools and a sociable poolside bar. Recent Expedia and Tripadvisor guests repeatedly praise the welcoming staff, well-kept grounds and generally clean rooms. Included continental breakfast is a useful extra, and Duval Street is only a few blocks away.

The catch is room selection: these historic buildings aren't uniform, and smaller rooms can feel tight. Tripadvisor guests also mention uneven maintenance, though recent feedback remains strongly positive overall. Check the exact room category rather than assuming every booking means a standalone cottage or private patio. A nightly amenity fee and limited, paid parking weaken the value. We'd skip it if spacious rooms and consistently polished finishes are priorities.

Best for

  • couples exploring Old Town
  • travelers who prefer historic character
  • pool-and-bar downtime

Watch out for

  • small rooms and variable layouts
  • uneven maintenance in historic buildings
  • amenity fee and limited paid parking
Location
Walkable Old Town setting a few blocks from Duval, without being directly on the main nightlife strip.
Rooms
Check category details carefully: size, building placement and private outdoor space vary.
Cleanliness
Strong overall feedback, with recent Expedia guests repeatedly describing clean rooms and maintained grounds.
Service
Friendly front-desk staff and bartenders are recurring strengths; occasional service lapses appear on Tripadvisor.
Amenities
Three pools, Bungalow Bar, continental breakfast, live music and on-property bicycle rentals.
Fees and surprises
Check whether the nightly amenity fee applies to your reservation; limited parking and pets cost extra.

Axel's opinion, from the hotel's website and recent guest reviews, scored for what the hotel is. Sources: Hotel website · Tripadvisor · Expedia · Booking.com. Reviewed Oct 20, 2026.

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