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  • Select Datesto
  • 2 Guests / 1 Room
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    Carefree Key West Events & Weddings

  • Select Datesto
  • 2 Guests / 1 Room

Escape Together

Design your perfect Key West gathering: set among historical Key West Victorian and Bahamian homes, sailing into sunsets with a gentle sea breeze, and enjoying stylish spaces with island-chic vibes. Colorful culture, boundless outdoor adventures, and vibrant nightlife – the ideal recipe for an unforgettable group getaway.

group hotel reservation: cheers
Bride and Groom sitting on a swing kissing
Lighthouse Communal outdoor area

Cheers to the Good Life

Weddings, reunions, bachelor/bachelorette parties, bicycle tours. Celebrate with welcoming accommodations to spoil your group and make any gathering incredible.

  • Patio surrounded by trees

    Keep It Exclusive

    Want the place all to yourselves? Buy-outs are available at Ridley House, Ella’s Cottages, or the Elizabeth House at Winslow’s Bungalows—all within walking distance of dynamic Duval Street.

  • Group of people gathered

    Make It Happen Here

    Planning a family reunion, milestone birthday or a group gathering? Our spacious suites offer the ideal blend of relaxation and celebratory fun, with room for the whole gang.

  • Group of people cheering their drinks

    We’ll Help You Plan It

    Book a group dinner, cocktail reception or farewell brunch at our enchanting outdoor venues. Savor signature cocktails and indulge in creative cuisine provided by our catering partner.


Find the Perfect Setting for Your Group

Nestled throughout the heart of Old Town, our historic inns offer an eclectic range of accommodations, each with its own unique story to tell. Unified by stylish design elements—elegant summer cane beds and fresh pastel colors, lush landscaping and a spirit of inclusion—these inns invite your group to experience carefree camaraderie. Whether you prefer an entire small inn or a guest house for private use, let us know—we’re here to enhance your getaway.

To book your room block, contact us at [email protected]

Enjoy access to the following amenities:

  • Five unique inns, centrally located in Old Town Key West and walkable from Duval Street
  • Seven sun-dappled pools and two inviting pool bars
  • Morning coffee and tea service
  • In-room yoga mats and Turkish robes
  • Complimentary WiFi


A private dinner for up to 10 in our Hemingway Suite overlooking the Hemingway House and historic Whitehead Street.
We love putting together meeting offers and packages that reflect the fascinating history and free spirited vibe of Key West. From complimentary future stays to sunset cruises, you never know what perks we’ll come up with next.

Hemingway affair at lighthouse hotel


A private dinner for up to 10 in our Hemingway Suite overlooking the Hemingway House and historic Whitehead Street.

Group of friends

Start Planning Your Gathering Today

We’ll help you create a group gathering to remember. Start by filling out our RFP form and a member of our team will be in touch to guide you through the details to design your ideal event or group getaway.