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  • 2 Guests / 1 Room
  • The historic Key West lighthouse

    Buyouts & Room Blocks

  • Select Datesto
  • 2 Guests / 1 Room

Grand Group Getaways

Looking for the perfect destination for your Key West bachelorette, honeymoon, or family reunion? Our stylish suites are ideal for group escapes, special celebrations, and milestone trips. Room blocks are also available for larger gatherings that call for one-of-a-kind settings.

Winslow’s Bungalows

The Elizabeth St. Annex

Bring your group to the Elizabeth St. Annex, a standalone section of Winslow’s Bungalows featuring multiple cottages, a luxurious suite, and a private pool. With 11 spacious rooms available, everyone can enjoy ample space to unwind and create their own unforgettable Key West experience.

  • Exterior of Winslow's Bungalows

    Elizabeth Annex King

    Enjoy charming Victorian architecture in a tranquil oasis surrounded by lush landscaping.

    • 240-270 sq/ft
    • 1 King Bed
    • 2 People
  • Winslow Catherine Facade

    Elizabeth Annex King Patio

    Unwind with a refreshing dip or relax on comfortable outdoor seating after a day exploring Duval Street.

    • 240-270 sq/ft
    • 1 King Bed
    • 2 People
  • Winslow Room

    Elizabeth Annex King with Wrap Around Balcony

    Step back in time and immerse yourself in the charm of this Victorian treasure, beautifully adorned with original pine walls.

    • 440 sq/ft
    • 1 King Bed
    • 2 People
  • Lighthouse bed and nightstand

    Elizabeth Annex 1 Queen Patio

    Enjoy charming Victorian architecture in a tranquil oasis surrounded by lush landscaping.

    • 240 sq/ft
    • 2 Queen Beds
    • 4 People
  • 1 King Patio

    Elizabeth Annex Garden King with Gated Patio

    Sink into the charm of lush gardens, a gated patio, a basket chair to enjoy the salt air and sunshine.

    • 270 sq/ft
    • 1 King Bed
    • 2 People
  • Lighthouse room

    Elizabeth Annex King with Mobility Access

    Unwind with a refreshing dip or relax outdoors after a day exploring Duval Street.

    • 312 sq/ft
    • 1 King Bed
    • 2 People
Winslow Room
Winslows Bungalows

Maloney King Patio

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

  • 400 sq/ft
  • 1 King Bed
  • 2 People
Winslow Suite
Winslows Bungalows

1 King Treehouse Suite

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.

  • 600 sq/ft
  • 1 King Bed
  • 2 People
Lighthouse Hotel

Gather for mojito-infused celebrations and group getaways just steps from two of Key West’s most iconic landmarks – the Key West Lighthouse and the Hemingway Home & Museum. A neighborhood gem since 1858, Lighthouse Hotel encapsulates historic Key West at its most colorful, offering spacious suites and poolside social spaces, right around the corner from the best of Duval Street.

Enquire about Lighthouse Hotel

1 King Hemingway Suite bed

King Hemingway Suite

A two-story loft fit for a legend, with 900 square feet of impressive architecture with stunning exposed wood beams. A self-contained oasis, complete with living and dining areas, a wrap-around balcony, luxurious soaking tub, and kitchen.

  • 900 sq/ft
  • 1 King Bed
  • 2 People
1 King and 1 Queen Loft Suite

King and Queen Isabel Loft Suite

Unwind amidst a bit of Key West History. This spacious and sun-drenched two-story loft offers king and queen beds for flexible comfort. Sip your morning coffee or bask in the golden hour light on your private gated patio.

  • 450 sq/ft
  • 1 King Bed + 1 Queen Bed
  • 4 People