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
Keys Cove Resort | Marathon Rental Homes
Spacious 4-bedroom, 3-bathroom vacation homes in Marathon, FL, featuring private pools, boat slips, and access to a private beach.
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.
Islamorada
Three Waters Resort & Marina
Escape to Three Waters Resort & Marina for island luxury, ocean views, and endless adventure.Three Waters Resort & Marina, a Tribute Portfolio Resort, is a newly reimagined oceanfront destination in Islamorada, Florida, blending island charm with modern luxury.
Meetings Max
120
Total Space
1680 sq ft
Largest Room
1680 sq ft
Marathon
Sun Outdoors Marathon
Sun Outdoors Marathon: waterfront RV resort with marina and Gulf views.
Key Largo
Largo Resort
A private waterfront sanctuary in Key Largo with lush tropical design, infinity pool, and full property buyout for unforgettable gatherings.
Key West
Key West Historic Inns
Key West Historic Inns — a curated collection of five distinctive, historic properties in Old Town Key West offering boutique stays steeped in island charm.
Weddings Max
100
Meetings Max
25
Marathon
Caribbean Soul Charters
Waterfront Florida Keys rental with sailboat included—perfect for sailors and nature lovers!
Marathon
Casa Clara Condominium
Casa Clara Condos in Key Colony Beach offers oceanfront 2-bedroom, 2-bathroom condos with private balconies, a heated pool, tennis courts, and beach access. Ideal for both short and long-term stays.
Key West
Garden House Hotel
The Garden House is a charming bed & breakfast nestled in Old Town Key West, offering cozy accommodations, a tranquil garden pool, and personalized concierge services—all just steps from Duval Street.
The Lower Keys
Veterans Dive Center & Retreat
Veterans Dive Center & Retreat — dive shop and veteran-friendly retreat in Summerland Key, Florida.
Marathon
Terra Marine Park
55+ pet-friendly manufactured home community with 23 homes, laundry, fishing, and picnic spaces.
Key West
Vacation Homes of Key West
Vacation Homes of Key West is a locally owned boutique vacation rental company offering a curated collection of authentic island-style homes.
Islamorada
Beach House at Tarpon Point
Luxury oceanfront home with stunning views, private beach, and pool.
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.
