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Gather in Key West
From milestone celebrations and wedding weekends to family reunions, group getaways, and gatherings worth traveling for, Key West Historic Inns gives you five distinct ways to bring everyone together. Reserve a room block, make an inn your own with a buyout, or gather over cocktails, dinner, and celebrations designed around your group. Our team is here to help make the details easy, so you can focus on making the most of Key West together.
CHOOSE YOUR STAY
Five Inns.
Find the One for Your Group.
Every gathering has its own personality, and so do our five inns. From lively poolside stays and intimate Old Town settings to romantic cottages, residential retreats, and an easygoing base for exploring, find the stay that fits your group and make Key West yours.
Winslow's Bungalows
At Winslow’s Bungalows, the Elizabeth Estate features 11 spacious rooms, including charming cottages and a signature suite, plus its own pool. Reserve the entire estate and host poolside gatherings for up to 40 guests, from welcome cocktails to celebratory pool parties.
Lighthouse Hotel
Gather at Lighthouse Hotel, steps from some of Key West’s most iconic landmarks. Reserve a room block, add the Hemingway Suite for a bridal, hospitality, or VIP suite, and host brunches, lunches, cocktail receptions, or pool parties for up to 60 guests at poolside Isabel’s.
Ella's Cottages
Make Ella’s Cottages entirely yours with a full buyout of all 22 rooms and suites. Transform the Hospitality Nook into a bridal or groom suite, then gather poolside for a welcome celebration or farewell reception for up to 40 guests.
Ridley House
Make Ridley House your own with a full buyout of all 23 rooms and suites. Your group can gather for chef-led breakfasts, lunches, dinners, and cooking experiences, plus poolside celebrations for up to 40 guests in a gracious Old Town setting.
Fitch Lodge
For groups ready to explore, Fitch Lodge is an easy Old Town home base. Just two blocks from the Historic Seaport, it puts fishing, diving, dining, and waterfront adventures within easy reach.
wedding weekends
Perfectly positioned near some of Key West’s most memorable wedding venues, our inns offer a beautiful home base for your guests and wedding party throughout the celebration. From welcome gatherings to farewell brunches, make the entire weekend part of the occasion with thoughtful room block enhancements, including:
- Preferred accommodations for the couple
- Welcome parties and pre-wedding gatherings
- Farewell brunches and poolside gatherings
- Getting-ready spaces with food and beverage options
- Welcome bag delivery or placement at check-in
- Personalized booking link for wedding guests
- Access to preferred Key West vendor recommendations
- Special first anniversary stay offer for the couple
ROOM BLOCKS
Keep Your Group Together
Make staying together part of the experience with a room block at one of our five Old Town inns. From wedding weekends and family reunions to milestone celebrations and group getaways, we’ll help coordinate accommodations that fit your group, with everyone close to the best of Key West.
Room Block Benefits & Amenities
Dedicated room blocks for your group with full inn buyouts available at select properties
Seven pools and two poolside bars across the collection
Live music and entertainment
Complimentary Wi-Fi, In-room yoga mats, Daily breakfast at participating inns
Options for welcome gatherings, farewell events, and celebrations
KEY WEST IS CALLING
Every great gathering starts with a plan. Tell us what you have in mind through our RFP form, and our team will help bring the details together, from the right inn and room block to celebrations, events, and experiences made for your group.