Winslow's Bungalows

4

725 Truman Avenue
Key West, FL 33040

Exterior

Enchantment awaits in the vibrant center of Old Town, just steps from Duval Street and the best of Key West. Discover our inviting resort-like retreat where every room is unique, and each stay is unforgettable. Playful, expansive, and exceptionally lush, with timeless historical architecture and three sun-dappled pools.

We welcome all guests to experience the eclectic, carefree spirit of Key West. Our charming accessible rooms are thoughtfully designed to ensure your safety and comfort, with stylish decor that brings in the best of our timeless tropical surroundings.

  • Elizabeth Annex 1 Queen Patioshow details

    Elizabeth Annex Room with Queen Bed Enjoy charming Victorian architecture in a tranquil oasis surrounded by lush landscaping. Unwind with a refreshing dip or relax on comfortable outdoor seating after a day exploring Duval Street.
    • Non-Smoking
  • Elizabeth Annex Garden King with Gated Patioshow details

    Elizabeth Annex Room with King Bed Your private Key West sanctuary awaits. Sink into the charm of lush gardens, a gated patio, a basket chair to enjoy the salt air and sunshine. Unwind by day, sink into a king bed by night.
    • Non-Smoking
    • 1 King
  • Elizabeth Annex Kingshow details

    Guest Room with King Bed Enjoy charming Victorian architecture in a tranquil oasis surrounded by lush landscaping. Unwind and relax after a day exploring nearby Duval Street.
    • Non-Smoking
    • 1 King
  • Elizabeth Annex King Mobility Accessshow details

    Elizabeth Annex Room with King Bed Enjoy charming Victorian architecture in a tranquil oasis surrounded by lush landscaping. Unwind and relax after a day exploring nearby Duval Street.
    • Non-Smoking
    • 1 King
  • Elizabeth Annex King Patioshow details

    Guest Room with King Bed Enjoy charming Victorian architecture in a tranquil oasis surrounded by lush landscaping. Unwind with a refreshing dip or relax on comfortable outdoor seating after a day exploring Duval Street.
    • Non-Smoking
    • 1 King
  • Elizabeth Annex King with Wrap around Balconyshow details

    Elizabeth Annex Room with King Bed Step back in time and immerse yourself in the charm of this Victorian treasure, beautifully adorned with original pine walls. Enjoy your morning coffee or an evening drink on your private wrap-around balcony.
    • Non-Smoking
    • 1 King
  • Kingshow details

    Guest Room with King Bed Indulge in the luxe comfort of your king bed and immerse yourself in the brightly lit, calming vibe of this room. Complete with everything you need for an unforgettable Key West stay.
    • Non-Smoking
    • 1 King
  • King Balconyshow details

    Balcony Room with King Bed A 30-square-foot balcony provides the perfect place to bask in the Key West Sunshine and enjoy an afternoon cocktail. Inside, find eclectic comfort and a plush king bed.
    • Non-Smoking
    • 1 King
  • King Bungalowshow details

    Balcony Room with King Bed Live like a local in authentic Key West conch homes brimming with vibrant colors. Cane furnishings create a warm, carefree bohemian ambiance, immersing you in island life.
    • Non-Smoking
    • 1 King
  • King Mobility Access Roll In Showershow details

    Balcony Room with King Bed All the inviting and stylish decor you expect from Winslow’s Bungalows, along with thoughtful accessible touches including a roll-in shower to ensure your safety and comfort.
    • Non-Smoking
    • 1 King
  • King Patioshow details

    Patio Room - Patio Area Step outside onto your 35-square-foot patio to bask in the Florida sunshine. Inside, sink into the plush comfort of a king bed and indulge in luxe bath amenities.
    • Non-Smoking
    • 1 King
  • Mallory King Patioshow details

    Balcony Room with King Bed Experience the carefree vibes of Key West in this spacious and premium room, featuring a plush king bed and soaking tub for ultimate relaxation.
    • Non-Smoking
    • 1 King
  • Poolside King with Patioshow details

    Patio Room - Patio Area Immerse yourself in the Key West lifestyle with easy access to our sparkling pool. Cane furniture creates an island ambiance, seamlessly blending your private patio with your luxurious room.
    • Non-Smoking
    • 1 King
  • Queenshow details

    Guest Room with Queen Bed Get the most out of your Key West getaway and enjoy a plush queen bed, timelessly charming island-chic decor, and Atelier Bloem bath amenities.
    • Non-Smoking
  • Treehouse Suiteshow details

    Treehouse Suite - Living Area Welcome to your home away from home in the heart of Key West! Our largest suite boasts 600 square feet of comfort. Enjoy a separate living area, a full bath and shower, and a spacious balcony for a truly resort-like experience.
    • Non-Smoking
    • Suite
  • Truman King Patioshow details

    Guest Room with King Bed Enjoy a birds eye view of the lobby pool and the neighboring Basilica of St. Mary Star of the Sea while enjoying a spacious accommodation with sofa bed and patio for enjoying the Key West sunshine.
    • Non-Smoking
    • 1 King
  • Two Queenshow details

    Guest Room with Two Queen Beds An ideal stay for up to four guests. Two queen beds offer plenty of space for your small group to unwind in style.
    • Non-Smoking
    • 2 Queen
  • Two Queen Poolside Mobility Access Roll In Showershow details

    Guest Room with Two Queen Beds Spacious and stylish, with two queen beds offering plenty of room for group getaways and family vacations. Accessible touches provide comfort and safety for all guests. Fitted with a gated patio poolside offering all of the Key West sunshine and splashes.
    • Non-Smoking
    • 2 Queen

Diningshow details

Bungalows Bar

Bungalow’s Bar
Retreat into a lush and welcoming oasis of specialty cocktails, anytime bubbles, and ice-cold beer. Whatever you’re craving to quench your thirst, order it poolside as the salty Key West breeze cools down your skin. Contemporary mixology meets timeless beauty among the enchanting charm of Winslow’s Bungalows. Easy, breezy, and as boozy as you’d like.

Amenitiesshow details

Outdoor Pool

Take a splash in our inviting pools or take an adventure through our winding walkways. Experiences that provide exceptional service that create a resort-like experience.

  • Free Breakfast
  • Pets Are Welcome
  • Pool (Outdoor)
  • No Smoking Rooms
  • Handicapped Accessibility

*Amenities offered are determined by the hotel and are subject to change. Please contact the hotel directly to determine current amenities provided.

Policiesshow details

Please note: Guests will be required to present a valid photo ID and a credit card upon hotel check-in. Hotel package prices include room and room tax only, and do not cover incidental charges, parking fees, cleaning fees, or resort fees which some hotels may collect upon check-in. In most cases, guests must be at least 21 years old to check in and there must be one person at least 21 years old staying in each room. Most hotel check-in times are 2:00pm to 3:00pm and most hotel check-out times are 11:00am to 12:00pm. To avoid confusion, please note that your flight departure date and time may be different from your hotel checkout date and time.

Check-in: 4pm Check-out: 11am Minimum Check-in Age: 18
Resort Fees Applicable: Yes
Resort Fees Include:

The USD $41.63 (plus tax) per room, per night Resort Fee includes:

  • Continental Breakfast
  • Onsite Concierge
  • Turkish Robes
  • Welcome Beverages
  • Yoga Mats
  • Afternoon Poolside Refresher
  • Wifi
Parking Fees Applicable: Yes

Self-Parking: USD $30 (plus tax) per vehicle, per night