Places to Stay

Cayo Hueso Resorts offers tropically elegant vacation rentals in Old Town Key West. Choose from private 1–3 bedroom bungalows, cottages, and homes, just steps from Duval Street.

The Caribbean Resort in Islamorada offers 22 private, Caribbean-style homes with ocean views, a beach-entry pool, fishing pier, and complimentary use of bicycles, kayaks, and paddleboards.

Rainbow Bend Resort is a family-friendly, oceanfront retreat in Marathon, Florida, offering a private beach, saltwater pool, and hot tub with ocean views.

Sunset Key Cottages is a luxury resort situated on a 27-acre private island just 500 yards off Key West, offering upscale one- to four-bedroom cottages with wraparound verandas and panoramic ocean views.

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.

Luxurious Key West stays with ocean views, private suites, and island charm.

Coconut Palm Inn is a boutique beachfront hotel on the Florida Bay in Tavernier, offering 450 feet of private beach, 19 stylish rooms and suites, and spectacular sunset views. Ideal for couples and small groups seeking a tranquil Keys retreat.

Mitchell’s Keys Villa is a secluded waterfront vacation rental in Islamorada, offering a private beach, marina, and boat ramp, ideal for fishing and relaxation.

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.

Hampton Inn Key Largo is a tropical hotel located on Florida Bay, offering free hot breakfast, an outdoor pool, fitness center, and complimentary WiFi. Guests can enjoy a private beach, boat dock, and easy access to nearby attractions like John Pennekamp Coral Reef State Park.

Bay Harbor & Coconut Bay Resort offers a tranquil waterfront escape in Key Largo, featuring 23 charming cottages, a private beach, and lush tropical gardens.

Looe Key Reef Resort offers beachfront accommodations, daily scuba and snorkeling trips, a full-service dive shop, and a Tiki Bar with live entertainment in the Florida Keys.

The Cabana Inn is an adults-only boutique hotel nestled just one block from Duval Street in Old Town Key West.

Fairfield Inn & Suites Key West at The Keys Collection is a newly renovated, family-friendly hotel near the airport offering a heated outdoor pool, fitness center, and complimentary breakfast—perfect for convenient island getaways

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.