Winslow’s Bungalows — Key West Historic Inns Overview
Key West, Florida
Photos courtesy of the hotel.
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Winslow’s Bungalows is a charming boutique hotel in Key West, Florida, located within the island’s historic district and part of the beloved Key West Historic Inns collection. Spread across several beautifully restored Victorian-era homes, this hidden oasis captures the relaxed spirit of Old Key West while offering modern comfort, thoughtful design, and lush tropical surroundings.
Set just a few blocks from lively Duval Street, the property feels worlds away from the crowds. Shaded walkways, palm trees, and tropical gardens connect a collection of pastel-colored bungalows that create an intimate, residential-style atmosphere. The result is a boutique Key West hotel experience that blends historic charm with the easygoing pace of island life.
Guests staying at Winslow’s Bungalows enjoy a peaceful retreat that still places them close to Key West’s most iconic attractions. Whether you’re spending the afternoon lounging by the pool, biking through historic streets, or heading out for sunset celebrations at Mallory Square, this historic Key West inn offers an authentic island stay perfect for couples, weekend escapes, and relaxed tropical vacations.
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Multiple heated outdoor pools surrounded by tropical gardens
Complimentary continental breakfast each morning
Beautifully restored historic Key West homes and bungalows
Private verandas, balconies, and outdoor seating areas
Complimentary bicycles for exploring Old Town Key West
Lush tropical landscaping with quiet courtyards and hammocks
Walking distance to Duval Street dining, bars, and nightlife
Relaxed island atmosphere with boutique hotel service
Easy access to beaches, sunset cruises, and historic sites
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Couples looking for a romantic Key West escape
Weekend getaways in Old Town Key West
Travelers who love historic inns and boutique hotels
Friends’ trips exploring the Florida Keys
Relaxed tropical vacations with walkable attractions
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Winslow’s Bungalows places you in the heart of Old Town Key West, close to many of the island’s most iconic attractions.
Nearby highlights include:
Duval Street – Key West’s famous strip filled with restaurants, bars, and live music
Ernest Hemingway Home & Museum – One of the island’s most historic landmarks
Mallory Square Sunset Celebration – A nightly festival celebrating the famous Key West sunset
Southernmost Point Buoy – The iconic marker just 90 miles from Cuba
Fort Zachary Taylor Historic State Park – One of the best beaches in Key West
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