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Carefree Key West Events & Weddings
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.
GET SOCIAL
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.
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.
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.
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.
ROOM BLOCKS
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
Promotions
KEY WEST MEETING OFFERS
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.
A HEMINGWAY AFFAIR AT LIGHTHOUSE HOTEL
A private dinner for up to 10 in our Hemingway Suite overlooking the Hemingway House and historic Whitehead Street.
REQUEST FOR PROPOSAL
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.
