top of page
Winslow’s Bungalows — Key West Historic Inns

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

Request a Custom Quote
& Free Trip Planning

Let me take care of everything - from finding the best available rate to securing VIP perks and personalized recommendations at no extra cost.

Book on Your Own

You can book on your own using the button below

but you’ll miss out on added perks, upgrades, and support.

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.

Winslow’s Bungalows — Key West Historic Inns
Winslow’s Bungalows — Key West Historic Inns

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.

bottom of page