Places to Stay
Claim your corner of The Florida Keys & Key West. Waterfront resorts, tucked-away inns, vacation rentals with a dock out back, campgrounds under the palms...however you like to unwind, there's a place here that gets it. Filter by destination, amenities or whatever matters most and find the spot that turns your trip from planned to perfect. Checkout is the only thing that should stress you out.
Filters
Marathon
Coconut Cay Resort & Marina
Escape to Coconut Cay Resort in Marathon, FL—serene waterfront stays with free bikes, kayaks, and nearby beaches.
Islamorada
Florida Keys Brewing Co.
Florida Keys Brewing Co. is the Upper Keys’ first microbrewery, serving award-winning craft beers in a vibrant beer garden and taproom located in Islamorada’s Morada Way Arts District—perfect for beer lovers and locals alike. Also offers a vacation rental.
Islamorada
Islander Resort
Escape to Islander Resort: vibrant Florida Keys stays, beachside dining, and endless adventures!
Meetings Max
1000
Total Space
19000 sq ft
Largest Room
2760 sq ft
Key West
Speakeasy Inn
The Speakeasy Inn is a historic adults-only guesthouse in Old Town Key West, offering tropical-themed suites, a wraparound porch, and a Rum Bar featuring over 350 rums.
The Lower Keys
Veterans Dive Center & Retreat
Veterans Dive Center & Retreat — dive shop and veteran-friendly retreat in Summerland Key, Florida.
Key West
Pegasus International Hotel
Stay in the heart of Key West with stylish rooms, rooftop pool, and free breakfast!
Key Largo
Sun Outdoors Key Largo
Sun Outdoors Key Largo: year-round, all-ages RV resort with a marina.
Weddings Max
50
Islamorada
Nest Villa at Holiday House
The Nest Villa in Islamorada is a private upper-level retreat with two bedrooms, panoramic Florida Bay views, and marina access with free dockage.
Marathon
Grassy Flats Resort & Beach Club
Eco-friendly boutique resort in the Florida Keys with oceanfront dining, water sports, and unique "olde Florida" charm.
Key West
Orchid Key Inn
Orchid Key Inn is an adults-only boutique hotel on Duval Street, offering stylish rooms, a tropical pool with a hot tub, and a vibrant poolside bar, all within walking distance of Key West's top attractions.
Marathon
Key Colony Beach Realty, Inc.
Keys Properties offers curated waterfront rentals and real estate in Key Colony Beach, including over 50 vacation homes with owner-managed care.
Key West
Ella's Cottages
Bohemian Key West charm awaits at Ella’s Cottages—stylish, cozy, and full of island spirit.
Key West
Boyd's Key West Campground
Boyd’s Key West Campground offers a variety of accommodations including RV sites, tiny homes, and tent camping.
Islamorada
Drop Anchor Resort & Marina
Drop Anchor Resort & Marina offers oceanfront accommodations with full kitchens, a heated pool, complimentary kayaks, paddleboards, and bicycles, all set in a tropical garden atmosphere. Ideal for couples and families seeking a relaxing Florida Keys getaway.
Islamorada
Mermaid's Bay Boutique Estate
Mermaid’s Bay is a secluded boutique estate in Islamorada, offering three private waterfront homes with resort-style amenities, ideal for group getaways
