Places to Stay

Island House Key West is a private, adults-only clothing-optional resort with a heated pool, sauna, gym, and 24/7 café/bar in Old Town.

Cheeca Lodge & Spa is a luxury oceanfront resort in Islamorada, offering elegant rooms, a 9-hole golf course, multiple dining options, and a full-service spa. Ideal for couples and families seeking a tranquil Keys getaway.

Conch Key Villas offers charming waterfront accommodations on Conch Key, featuring fully equipped studios with private boat slips, ideal for fishing enthusiasts and couples seeking a tranquil retreat.

Heart of Morada — luxury 3-bed vacation home with private pool, boat dock & kayaks in the heart of Islamorada, Florida Keys.

Stay in a charming Victorian Key West inn with unique rooms, pool, and breakfast.

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.

Escape to Seabird Key: private 10-acre island retreat in Marathon, FL.

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

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.

Captain Pip’s Marina & Hideaway offers waterfront accommodations in Marathon, FL, featuring cozy rooms and 1- and 2-bedroom apartments with kitchenettes.

Center Court Key West offers boutique vacation rentals in Old Town, featuring 9 private suites with heated pools, lush gardens, and a central location just steps from Duval Street.

Luxury beachfront resort in Key Largo with stunning bay views, spa, and watersports.

Gilbert’s Resort & Marina is a laid-back waterfront resort in Key Largo, featuring waterfront rooms, a private beach, and the Keys’ largest tiki bar with live music and dining.