Places to Stay

Explore KeysCaribbean: Expert hotel management and luxury vacation rentals.

Stay inspired in a charming Key West guesthouse honoring literary legends.

Coconut Palms of Key West offers spacious 2- and 3-bedroom beachfront condos at 1800 Atlantic Resort, adjacent to Smathers Beach. Enjoy ocean views, a heated pool, and easy access to water activities.

Southernmost Beach Resort is one of Key West's most iconic beachfront resorts, offering four romantic wedding venues from private beach ceremonies to poolside celebrations at the quiet end of Duval Street, with full-service catering and a dedicated team to bring your dream day to life.

Key West Historic Inns — a curated collection of five distinctive, historic properties in Old Town Key West offering boutique stays steeped in island charm.

Key Largo Inn offers budget-friendly, Caribbean-style accommodations with a pool, full bar, and dive shop, centrally located in Key Largo.

White Gate Court is a charming, pet-friendly boutique resort nestled on three lush acres in Islamorada, offering seven unique cottages with old Keys-style charm.

Full-service marina in Tavernier offering wet slips, dry storage, houseboat rentals & resort amenities in a protected mangrove setting.

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.

Luxury waterfront vacation rentals in Marathon & Key Colony Beach, FL. Private pools, docks, and dog-friendly accommodations. Sleeps 8–10.

The Nest Villa in Islamorada is a private upper-level retreat with two bedrooms, panoramic Florida Bay views, and marina access with free dockage.

Seven Keys Vacations is a locally managed Florida Keys vacation rental company with over 200 homes, condos, and waterfront properties stretching from Key West to Key Largo — your one-stop shop for oceanfront escapes, canal-front retreats, pet-friendly homes, private pools, and boat dock properties throughout the Keys.

Dream Bay Resort is a private, gated resort and wedding venue in Key Largo, offering five charming cottages, a small marina, and breathtaking sunset views over Florida Bay. Ideal for romantic getaways and intimate weddings.

Islamorada Vacation Rentals offers a curated selection of vacation homes and cottages in the Florida Keys, providing travelers with diverse options for a memorable stay.