Kimpton Winslow's Bungalows

Historic Highlight

fromUSD $247*night
Includes all taxes & fees
*Based on a 3 night stay, from Mon, Sep 18 to Thu, Sep 21. Perks may not apply to this rate. view this rate

Key West, Florida

Kimpton Winslow's Bungalows

Historic Highlight

What it is

First established in 1856, this collection of fanciful former homes now has 85 guest rooms, three pools, and two bars that specialize in local libations (get the Rum Runner).

What it isn't

Lifeless. The property is named for landscape painter Winslow Homer, who summered here.

What we think

Nobody comes to Key West for a bad time, so it’s no wonder pet-friendly Kimpton has pushed the fun factor full-throttle at Winslow’s Bungalows. For proof, look no further than the fact that guests have access to a fleet of custom-made loaner bikes, snorkeling gear they can lug to any of the nearby beaches, and will be treated to a boozy cocktail upon arrival. Even the interior decor is as frothy as nearby shores; rooms are adorned with beachy rattan furniture, textiles and art as bright as a Hawaiian shirt, and those jalousie slatted windows that are so common in the Caribbean climate. Because starter rooms can be cozy at 185 square feet, we recommend upgrading to a King Suite (300 square feet) or even the 595 square foot Tree House Suite, which has soaring ceilings and a deep tub that says “Vacay” at a glance. Either way, expect pampering in the form of Atelier Bloem toiletries, Samsung HD TVs, cushy robes, and Kimpton’s trademark in-room yoga mats.

You're here because

You’re always determined to kick-start the day right, and love that the hotel includes continental breakfast, coffee, and tea service in the amenities fee. Oh, did we mention the afternoon poolside refreshers?

The Moment

Perched on a rattan-wrapped stool at the poolside bar Shaken + Stirred, you can’t help but order a Mai Tai. You may not literally be wearing a flower necklace, but you’re going to drink like it.

Restaurants & Bars

Bungalow Bar - outdoor pool bar offering cocktails, beer and wine

Isabel's Bar - poolside bar offering cocktails, beer and wine


The vibrant heart of Key West’s Historic District, just four blocks from the Key West Lighthouse and five from the 1851 Hemingway Home and Museum, where the author lived with his famously six-toed cats.

725 Truman Avenue
Key West, 33040
FL, United States

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