
Winslow’s Bungalows — Key West Historic Inns
Key West, Florida
Best For
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
Location Highlights
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
Rates & Booking Options
Winslow’s Bungalows — Key West Historic Inns
Key West, Florida
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.
Key Amenities & Experiences
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
VIP Perks When You Book With Me
When you book Winslow’s Bungalows through me as your travel advisor, you’ll receive exclusive perks that elevate your Key West stay:
Early check-in and late check-out, based on availability
Upgrade to the next room category, subject to availability
Complimentary continental breakfast
25% off food and beverages once per stay
Handwritten personalized welcome card
Bottled water in room upon arrival
VIP guest profile recognition for your stay
Beyond these perks, I also provide personalized travel planning support, including recommendations for Key West restaurants, sunset cruises, snorkeling tours, and the best ways to experience the island’s laid-back charm.
Plan Your Stay
Ready to book your getaway?
Complete the short form below - I’ll send you a custom quote with your VIP perks and take care of the details.
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