Winslow's Bungalows - Key West Historic Inns

Key West, Florida

A pocket of laidback luxury fitted amongst the sun-drenched Florida Keys.

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Property Overview

Winslow's Bungalows spans a lush, landscaped campus in the heart of Old Town, Key West. Named for famous painter and summer resident Winslow Homer, this expansive haven boasts three private pools, an outdoor bar and vibrant gardens. It’s an idyllic scene those looking to explore this corner of the Keys at their own pace.


SmartFlyer Exclusives

  • Upgrade upon arrival, subject to availability
  • $50 USD Hotel Credit
  • Bottled water and snacks in room
  • VIP status
  • Complimentary Wi-Fi


Agent Tips

  • Rooms with a patio are a must-stay: it's the perfect place to enjoy the immaculate Key West weather.
  • Try one of the bar's signature Keyzy cocktails like the Key West Cooler: Tito’s vodka, cranberry, coconut, and orange.
Rooms + Suites

A pocket of laidback luxury to revel in.

With eighty-five guestrooms including two deluxe suites, Winslow's Bungalows is a newly-renovated expansive haven that extends across several historic Key West architectural styles. Its colorful history is matched by the artful, bohemian interiors and elegant touches like summer cane beds, European armoires, and maritime basket lighting. Communication accessible features are available upon request.

There are three pools.

There are three pools at Winslow's Bungalows: one tranquility area, one with a bustling bar side, and one features a spacious deck space for ample stretching room.

A great spot to kick back.

The Bungalow Bar is a great spot to kick back after a long day cruising around the city. We recommend sipping on a banana daiquiri, made with bananas grown fresh on the property.
Who's it for?

Best suited for couples and groups of friends

Winslow's Bungalows is best suited for couples and groups of friends. The hotel sits in an ideal spot where guests can roll right out of bed and into the heart of Old Town and stroll down the iconic Key West coastlines.
  • Location
    Winslow's Bungalows is located in the quiet end of Old Town Key West, still walkable to all there is to do on the island like a drink on the happy hour-filled Duval Street and a street show in Mallory Square.

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