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  • Select Datesto
  • 2 Guests / 1 Room
  • Winslow Lobby

    Stay at Winslow’s Bungalows

  • Select Datesto
  • 2 Guests / 1 Room

An Enchanting, Resort-Like Retreat

Discover a lush and vibrant oasis in the heart of Old Town, where each room reflects the timeless and authentic spirit of Key West. Winding walkways, inviting pools, and exceptional service create a resort-like experience, perfect for large groups, families and wedding parties.

  • 1 King bedroom
  • 1 King Patio washroom
  • Winslow Restroom

King

  • 2 People
  • 1 King
  • 240-270 sq/ft

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.

  • 1 King Patio
  • 1 King bedroom
  • Winslow Exterior walkway
  • Three Winslow's bungalows

King Patio

  • 2 People
  • 1 King
  • 180-312 sq/ft

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.

  • Winslow Suite
  • Winslow Suite living room
  • Winslow Suite living room
  • Winslow Suite Restroom
  • Winslow Suite Restroom
  • Winslow Suite Sun Deck

Treehouse Suite

  • 2 People
  • 1 King
  • 600 sq/ft

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.

  • Fitch Lodge Room side table
  • side table with blue phone
  • Ellas Restroom
  • Lighthouse room

One Queen

  • 2 People
  • 1 Queen
  • 240 sq/ft

Get the most out of your Key West getaway and enjoy a plush queen bed, timelessly charming island-chic decor, and luxurious bath amenities.

  • 2 Queen bedroom
  • 2 queen bathroom
  • 1 King Soaking Tub
  • side table with blue phone

Two Queen

  • 4 People
  • 2 Queen
  • 240 sq/ft

An ideal stay for up to four guests. Two queen beds offer plenty of space for your small group to unwind in style.

  • Winslow Room
  • Winslow Room
  • Winslow Room
  • side table with blue phone
  • 1 King Soaking Tub

Maloney King

  • 2 People
  • 1 King
  • 400 sq/ft

Experience the carefree vibes of Key West in this spacious and premium room, featuring a plush king bed and soaking tub for ultimate relaxation.

  • Winslow Room
  • Lighthouse room
  • 1 King Sofa Bed Patio bathroom
  • Bathroom double sink

King Sofa Bed Patio

  • 4 People
  • 1 King
  • 325 sq/ft

Everything you need for a perfect Key West getaway. A patio for enjoying the sunshine, a sofa bed for extra lounge space, and a king bed for restful nights before your next adventure.

  • Lighthouse room
  • 1 King bedroom
  • side table with blue phone
  • 1 King Soaking Tub
  • key west building balcony

King Balcony

  • 2 People
  • 1 King
  • 255-310 sq/ft

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.

  • side table with blue phone
  • king bed with decorative pillow and phone
  • King Studio Suite bed and side table

King Mobility Access Roll in shower

  • 2 People
  • 1 King
  • 312 sq/ft

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.

  • Lighthouse bed and nightstand
  • side table with blue phone
  • Fitch Lodge Room side table

Two Queen Poolside Mobility Access Roll in Shower

  • 4 People
  • 2 Queen
  • 220-280 sq/ft

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.

  • Exterior of Winslow's Bungalows
  • 1 King bedroom
  • King Studio Suite bed and side table
  • Ridley Bedroom

Elizabeth Annex King

  • 2 People
  • 1 King
  • 240-270 sq/ft

Enjoy charming Victorian architecture in a tranquil oasis surrounded by lush landscaping. Unwind and relax after a day exploring nearby Duval Street.

  • Winslow Catherine Facade
  • one bedroom suite
  • side table and lamp

Elizabeth Annex King Patio

  • 2 People
  • 1 King
  • 240-270 sq/ft

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.

  • Exterior of Winslow's Bungalows
  • Winslow Room
  • 1 Bedroom Suite bed

Elizabeth Annex King with Wrap Around Balcony

  • 1 King
  • 440 sq/ft

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.

  • key west building balcony
  • Lighthouse bed and nightstand
  • 1 King Patio
  • side table with blue phone

Elizabeth Annex 1 Queen Patio

  • 4 People
  • 1 Queen
  • 240 sq/ft

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.

  • 1 King Patio
  • Winslow Room
  • side table and lamp

Elizabeth Annex Garden King with Gated Patio

  • 2 People
  • 1 King
  • 270 sq/ft

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.

  • 1 King bedroom
  • side table and lamp
  • 1 King Patio
  • Winslow Pool and seating area

Poolside King with Patio

  • 2 People
  • 1 King
  • 240-270 sq/ft

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.

  • key west building balcony
  • Lighthouse room
  • side table and lamp

Elizabeth Annex King with Mobility Access

  • 2 People
  • 1 King
  • 312 sq/ft

Enjoy charming Victorian architecture in an accessible oasis surrounded by lush landscaping. Unwind with a refreshing dip or relax outdoors after a day exploring Duval Street.

  • Three Winslow's bungalows
  • 1 King bedroom
  • King Studio Suite bed and side table
  • side table with blue phone

King Bungalow

  • 2 People
  • 1 King
  • 240 sq/ft

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.

  • Winslow Room
  • Winslow Room
  • 1 King Patio washroom

Truman King Patio

  • 2 People
  • 1 King
  • 325 sq/ft

Wake up to views of our sparkling pool and the iconic Basilica of St. Mary Star of the Sea. Enjoy an airy, light-filled room and indulge in your spacious soaking tub. Bask in the Key West sunshine on your patio.

Lighthouse bed and nightstand
Accessible Accommodations

Inviting Comfort for All

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.

What’s Included at Winslow’s Bungalows

  • Outdoor Pools
  • Complimentary Continental Breakfast
  • Concierge Services
  • Turkish Robes
  • Two Welcome Drinks at Bungalows Bar
  • On-site parking ($30/day)
  • Pet Friendly ($50/night)
  • Yoga Mats
  • Afternoon Poolside Refresher
  • Complimentary WiFi