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  • 2 Guests / 1 Room
  • Winslow Suite Sun Deck

    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.

  • Lighthouse room
  • Ellas Restroom

Key Lime

  • 2 People
  • 1 Queen
  • 240 sq/ft

A nod to the notorious namesake Key Lime Inn, these rooms feature one queen bed and a perfect getaway space for your Key West adventure.

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

Blue Parrot

  • 4 People
  • 2 Queen
  • 240 sq/ft

The Blue Parrot whisks you away to the history of Key West. Featuring two queen beds and nostalgic touches of our former namesake.

  • Three Winslow's bungalows
  • 1 King bedroom
  • side table with blue phone

Bungalow

  • 2 People
  • 1 King
  • 150 sq/ft

Live like a local in authentic Key West conch homes complete with a sun filled outdoor space.

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

Annex

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

The Elizabeth annex features a tranquil space adjacent to the grounds at Winslow's. Either a King or Queen bed set within a charming and historic Victorian home.

  • 1 King bedroom
  • 1 King Patio washroom
  • 1 King Soaking Tub

Winslow

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

Follow the winding brick walkways, indulge in the vibrancy of Winslow's and immerse yourself in Key West. Complete with everything you need for an unforgettable stay.

  • 1 King bedroom
  • Winslow Exterior walkway

Winslet

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

Fitted with a sunswept patio or balcony our Winslet rooms are complete with charm. Inside, enjoy modern boho chic features and carefree vibes.

  • Winslow Room
  • Winslow Room

Maloney

  • 2 People
  • 1 King
  • 400 sq/ft

Once owned by historian and army officer Colonel Walter Maloney, and featuring a king bed and soaking tub for ultimate relaxation.

  • 1 King Sofa Bed Patio bathroom

Truman

  • 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. Bask in the Key West sunshine on your patio.

  • 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
  • 425 sq/ft

Surround yourself high amongst the lush treeline of Key West. Enjoy a separate living area, a full bath and shower, and a spacious balcony listening to the nature around.

  • king bed with decorative pillow and phone
  • side table with blue phone

Winslow Mobility

  • 2 People
  • 1 King or 2 Queen
  • 175-225 sq/ft

Accessible touches provide comfort and safety for all guests.

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

Annex Mobility

  • 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.

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.

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