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Carefree Key West gatherings
Escape Together
Our hotels are the perfect setting for unforgettable group getaways, milestone celebrations, and special occasions. Whether you’re bringing together loved ones or rewarding your team, we’ve got the ideal space to make it happen. Looking for something more private? We offer room blocks and full hotel buyouts—plus, our team can help you host the perfect reception or event tailored to your guests.
GET SOCIAL
Cheers to the Good Life
Celebrate with welcoming accommodations to spoil your group and make any gathering incredible. Get to know each of our Inns, each offering one-of-a-kind settings and stories.
Winslow's Bungalows
Located in the resort-like Winslow’s Bungalows, the Elizabeth Annex offers 11 spacious rooms including multiple cottages, a luxurious suite and a private pool. When you reserve the entire home, our team can accommodate poolside events for up to 40 guests for the perfect welcome reception, cocktail hour or pool party.
Ella's Cottages
Reserve all 22 rooms and suites at the charming Ella’s Cottages and enjoy exclusive perks. The Hospitality Nook, used for Tea Time at Ella’s Cottages, can transformed into the ideal bridal or groom suite, plus we can put on a swanky poolside welcome or farewell reception for up to 40 people.
Ridley House
Nestled behind classic picket fences, Ridley House beckons you for an unforgettable stay where bohemian vibes meet upscale stays in a prime location. Reserve all of our 23 rooms and suites and your group can experience private breakfasts, lunches, dinners and cooking classes by our House Chef, as well as poolside gatherings for up to 40 guests.
Lighthouse Hotel
Gather for mojito-infused celebrations and group getaways at Lighthouse Hotel, just steps from Key West’s most iconic landmarks. Reserve your room block and include the luxurious Hemingway Suite for a bridal, hospitality or VIP suite. Lively receptions from brunches, lunches & pool parties for up to 60 guests include the use of our poolside bar, Isabel’s.
Fitch Lodge
Join us at Fitch Lodge, the destination for adventurers. These authentic historic conch homes are located just two blocks from the famous Key West Historic Seaport and all its fishing, diving, restaurants and culture to explore. A great option for room blocks, relax in comfortable accommodations with bohemian and tropical flair.
WEDDING WEEKENDS
Perfectly situated steps from Key West’s top venues, our Inns are the ideal location for hosting your guests, wedding party and pre and post nuptial events. Choose from a plethora of enhancements when you host our room block with us, such as:
- Sleeping Room Discount for Bride & Groom
- Welcome Party
- Farewell Brunch/Pool Party
- Bridal & Grooms Suites with food & drinks
- Gift Bags Delivered or at Check-In
- Booking Link for Your Guests
- Access to our Favorite Local Vendors List
- Sleeping Room Discount for Bride & Grooms for One Year Anniversary
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
- Breakfast daily along with coffee and tea service
- Live Music & Entertainment
- In-room yoga mats
- Complimentary WiFi
KEY WEST IS CALLING
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 group getaway.
