Places to Stay

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

Discover Winslow’s Bungalows: a vibrant, historic Key West oasis with pools, charm, and local tales.

Key Lime Sailing Club & Cottages offers a unique, all-inclusive waterfront retreat in Key Largo, featuring self-contained cottages with unlimited sailboat use, kayaks, snorkeling gear, and more.

Bohemian Key West charm awaits at Ella’s Cottages—stylish, cozy, and full of island spirit.

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.

Discover Island Villa: Luxury Florida Keys getaways await.

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.

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.

Pier House Resort & Spa is a historic oceanfront retreat in Old Town Key West, featuring a private white sand beach, full-service spa, three dining venues, and the iconic Chart Room Bar

Set on a private 60-acre oceanfront sanctuary, this resort offers spacious one- and two-bedroom suites, a private sandy beach, Jr. Olympic pool, deep-water marina, oceanfront gazebo, and tennis/pickleball courts.

Sugarloaf Lodge is a waterfront retreat located at Mile Marker 17 on the Overseas Highway, offering 31 rooms with private patios or balconies overlooking the serene Lower Sugarloaf Sound.

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.

Dragonfly Lite is a secluded 2-bedroom, 1-bathroom vacation home in Marathon, FL, featuring a private heated saltwater pool, outdoor shower, and lush tropical patio. Ideal for couples or small families seeking a tranquil retreat.

The Ocean View Inn & Sports Pub in Islamorada offers comfortable accommodations with a tropical flair, an outdoor pool, and a lively pub serving classic American fare and late-night bites.

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.