Places to Stay

Freewheeler Vacations is the Upper and Middle Keys’ largest and longest-running vacation rental company, offering everything from cozy condos to grand estates, backed by 30+ years of expert service.

Topsider Resort is a unique beachfront retreat in Islamorada, featuring charming octagonal stilted bungalows perched over the bay.

Keys Holiday Rentals offers vacation homes and condos in Islamorada, Florida Keys, perfect for waterfront stays, fishing trips, and family getaways.

Mermaid’s Bay is a secluded boutique estate in Islamorada, offering three private waterfront homes with resort-style amenities, ideal for group getaways

The Pelican Key Largo Cottages is a charming waterfront retreat located directly on Florida Bay in Key Largo, offering a serene and tropical escape just an hour from Miami International Airport.

Discover Jolly Roger RV Resort: spacious sites, stunning views, and island adventures!

Old Wooden Bridge Resort & Marina in Big Pine Key offers charming houseboat-style accommodations, a marina, an outdoor pool, and a prime location near the No Name Key Bridge and the National Key Deer Refuge.

Charming historic cottages in the heart of Old Key West, steps from Duval Street!

Banana Bay Resort & Marina in Marathon is a laid-back tropical retreat featuring 59 charming guestrooms, a private marina, and complimentary breakfast. Nestled on ten serene Gulf Coast acres, it's the perfect blend of coastal comfort and Florida Keys adventure.

Relax at Skipjack Resort & Marina in the Florida Keys—luxury suites, marina, pool, and fresh seafood!

Lime Tree Bay Resort offers beachfront accommodations with multiple heated pools, complimentary watersports, and boat dockage in the Florida Keys.

KeysCations offers a curated selection of luxury vacation homes in Marathon, FL, featuring private pools, docks, and ocean views. Ideal for families and groups seeking a tranquil Keys getaway.

Experience resort-style fun with the largest pool in the Florida Keys, ocean-view lounging, a speakeasy game room, marina access, and exclusive tennis and pickleball courts—including the Keys’ only indoor pickleball court.

Southernmost Beach Resort & Guesthouses is an oceanfront Key West escape featuring multiple heated pools, beachfront dining, a full-service spa, and lush tropical gardens just steps from Duval Street.

Parmer's Resort is a tranquil, waterfront retreat on Little Torch Key, offering a variety of accommodations, a 90-foot private beach, boat slips, and easy access to the natural beauty of the Florida Keys.