Places to Stay

Oceanfront 3BR rental in gated community with panoramic views, boat slip, and top Islamorada location.

Captain’s Quarters #415 — stylish 2-bedroom waterfront rental in the gated Venture Out community on Cudjoe Key, Florida Keys.

Sunshine Key Tiny House Village is a vibrant collection of colorful tiny homes located on Ohio Key, offering a unique and charming way to experience the beauty of the Florida Keys.

Southwinds Motel is a budget-friendly, adults-only hotel in Old Town Key West, offering two outdoor pools, complimentary continental breakfast, and convenient access to Duval Street and the Atlantic Ocean.

Dolphin Vacations offers a curated selection of vacation rentals in Key West and Marathon, FL, including historic homes and modern condos. Properties like Casa Rosa provide private pools and prime locations near Duval Street.

Monte Christo Condominiums is a luxury oceanfront retreat in Key Colony Beach, offering two- and three-bedroom condos with resort-style amenities.

The Galleon Resort & Marina is a waterfront resort in Old Town Key West offering spacious studios and suites with full kitchens or kitchenettes, a private beach, pool, and on-site marina—all just steps from Duval Street.

Historic Azul Key West offers a serene, romantic oasis just steps from vibrant downtown.

Marlin Bay Resort & Marina offers luxury vacation homes and a full-service marina with resort-style amenities in Marathon, Florida Keys.

Blue Flamingo Resort in Key West offers a reimagined getaway with tropical-style rooms, two lively pools with luxe cabanas, and poolside dining at Rum Row and Toasted Coconut.

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.

Tarpon Flats Inn & Marina is a boutique waterfront retreat in Key Largo, offering five spacious, air-conditioned rooms with kitchenettes, private beach access, and complimentary kayaks for exploring the surrounding waters.

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.

Bahia Honda State Park – Florida Keys gem with white-sand beaches, crystal-clear snorkeling zones, historic bridge views, and lush nature

Isla Bella Beach Resort offers luxury oceanfront rooms and suites, five pools, a full-service spa & multiple dining options—all set on over a mile of private beachfront