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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

1 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

1 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

1 King 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

1 Double

  • 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 Atelier Bloem bath amenities.

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

2 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

1 King Soaking Tub

  • 2 People
  • 1 King
  • 400 sq/ft

Indulge in elevated luxury with Atelier Bloem amenities in a deep soaking tub. Experience the carefree vibes of Key West in this spacious and premium room, featuring a plush king bed for ultimate relaxation.

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

1 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
  • kimpton key west building balcony

1 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

1 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

2 Queen 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.

What’s Included at Winslow’s Bungalows

  • Outdoor Pools
  • Complimentary Continental Breakfast
  • On-Site Concierge
  • Turkish Robes
  • Welcome Beverage
  • Limited On-Site Parking (nightly fee applied)
  • Pet Friendly (nightly pet fee applied)
  • Yoga Mats
  • Afternoon Poolside Refresher
  • Complimentary WiFi
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.