Winslow's Bungalows - Key West Historic Inns

725 Truman Ave, Key West, FL 33040, Key West, United States

4-star hotel

Guest rating: 4.4 / 5

Overview

Winslow's Bungalows - Key West Historic Inns is a 4-star boutique property set amid tropical foliage in the center of Old Town Key West. The hotel is arranged across multiple buildings, with bright, green-accented rooms that open onto garden areas. With a public rating of 4.4/5 from 1,312 reviews, it’s positioned as a well-liked, characterful stay in a walkable historic neighborhood.

Rooms

Accommodations are described as bright rooms with green accents, located in multiple buildings and oriented toward the gardens. Rooms include en suite bathrooms, free Wi‑Fi, flat-screen TVs, and air-conditioning; some units add minifridges, coffeemakers, and private patios. Guests frequently highlight comfort, while a few note that air-conditioning can be loud.

Amenities & Recreation

On-site features emphasize an outdoor, garden-forward layout, with abundant garden paths and cozy seating areas throughout the grounds. The hotel also has a heated outdoor pool. Parking is available for a fee.

Breakfast & On-site Service

A free continental breakfast is served poolside. Guest feedback points to a simple spread (such as pastries, bagels, fruit, coffee, and juice) and consistently friendly, hospitable staff.

Location & Nearby Highlights

In Old Town, the property is about a 5-minute walk to Duval Street’s restaurants and music venues and roughly an 8-minute walk (about 506 m) to The Hemingway Home and Museum. Other nearby landmarks include the Key West Lighthouse (561 m), the Key West Butterfly and Nature Conservatory (643 m), the Southernmost Point of the Continental U.S.A. (768 m), and the Truman Little White House (1,129 m). Mallory Square (1,372 m) and the Sunset Celebration at Mallory Square (1,379 m) are also close, as are waterfront and beach options like Fort Zachary Taylor Historic State Park Beach (1,637 m) and Smathers Beach (2,781 m).

Best for

This hotel suits travelers who want a boutique, garden-filled Old Town stay within easy walking distance of Duval Street and major Key West sights like the Hemingway Home and the Southernmost Point. It’s also a strong fit for guests who value a relaxed pool-and-gardens atmosphere, plus a convenient free continental breakfast served poolside.

Travel tips

Plan to explore Old Town on foot: the Hemingway Home and Museum (about 506 m) and Key West Lighthouse (about 561 m) are close enough for easy walks, and Mallory Square is roughly 1.4 km away for the evening Sunset Celebration. If you’re driving, factor in that parking is available but carries a fee. Consider requesting a room placement that suits your noise sensitivity, as some guests mention louder air-conditioning.

What guests say

Guests commonly praise the friendly, attentive service and describe the grounds as lush, tropical, and especially charming to walk through. Room comfort is a frequent positive theme, with the bungalow-style layout adding to the sense of privacy and atmosphere. The included continental breakfast is often noted as a convenient, straightforward spread served poolside. Location is repeatedly highlighted as a major advantage for reaching Duval Street and nearby landmarks on foot. A recurring drawback mentioned by some guests is that the air-conditioning can be noisy.

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