Places to Stay

Charming tropical boutique inn in historic Key West with pool, breakfast, and happy hour.

Orchid Key Inn is an adults-only boutique hotel on Duval Street, offering stylish rooms, a tropical pool with a hot tub, and a vibrant poolside bar, all within walking distance of Key West's top attractions.

Historic Key West Vacation Rentals offers a curated selection of luxury vacation homes, cottages, and condos in the Key West Historic District.

Tropical seaside stay with marina access and on-site dining.

Tea Table Key is a spectacular, car-accessible private island estate in Islamorada, spanning over 15 acres and offering complete exclusivity just off the Overseas Highway.

Premier short-term vacation homes and waterfront escapes in Key West and the Florida Keys with pool, beach access, pet-friendly stays, and local water activities.

Scuba Town USA in Islamorada offers an all-in-one dive and vacation experience with lodging, dining, pools, a private beach, and access to multiple dive-related businesses, all set within Three Waters Resort & Marina.

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.

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.

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.

The Conch House Heritage Inn is a historic adult-only bed and breakfast located in Old Town Key West. Guests enjoy elegant accommodations, a pool, daily breakfast with mimosas, and a prime location just steps from Duval Street.

Baker’s Cay Resort Key Largo — boutique waterfront resort with beach access, watersports, dining and family-friendly amenities in Key Largo, FL.

Morning Star Sailing Charters offers personalized sailing experiences in the Florida Keys, including captained and bareboat charters, sunset cruises, and snorkeling tours.

Stay at the iconic Southernmost House, an oceanfront boutique hotel blending historic charm with unforgettable Atlantic views.