Winslow's Bungalows

Name: Winslow's Bungalows
Address: 725 Truman Ave, Key West, FL, 33040, US
Price range: Starts at $500

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Select services venue

The venue will provide the space, plus a few extras.

Full wedding (ceremony and reception) pricing

Starting at $500

Guest capacity

Up to 50 seated guests

About this venue

Enchantment awaits at Winslow's Bungalows, an inviting, resort-like retreat nestled in the vibrant heart of Old Town Key West, just steps from Duval Street. Our unique property is steeped in history, having housed Key West’s first motel and welcomed a diverse cast of characters over the years. With three serene pools and a lush, welcoming atmosphere, Winslow's Bungalows offers an authentic and eclectic Key West experience. Our Innkeepers are eager to share the magic of this charming oasis, where whimsical touches sprinkle magic on your stay.

Seated guest capacity

Venue type

Hotels, Inns, Resorts

Venue setting

Covered Outdoor
Outdoor

725 Truman Ave, Key West, FL 33040

Our event spaces

Winslow's Bungalows

Enchantment awaits in the vibrant heart of Old Town.

Winslow's Bungalows offers intimate and exclusive outdoor spaces perfect for wedding parties and social gatherings, utilizing the charm of its historic grounds and bungalow architecture. • Poolside Oasis & Bungalow Bar: This central area, featuring multiple pools, is surrounded by lush tropical greenery and the clean white wood of the bungalows. The Bungalow Bar offers specialty cocktails and delightful poolside bites in a beautiful, open-air cabana setting with thatched rope lighting. This space is ideal for a welcome reception, sophisticated cocktail hour, or an intimate, relaxed reception dinner. • Elizabeth Annex (Private Buyout): Tucked away within the grounds, the Elizabeth Annex is perfect for group getaways and wedding parties, offering a private haven with its own serene pool and private sun deck. This exclusive area includes 11 spacious guest rooms, making it ideal for hosting the entire wedding party in one secluded, luxurious setting.