Best Resorts in Islamorada

Cheeca Lodge is the anchor resort of Islamorada — a 27-acre oceanfront property with a private beach, full-service spa, Jack Nicklaus golf course, saltwater lagoon pool, and on-site fishing charters. It is the most complete resort in the Upper Keys and the one most people picture when they think of Islamorada.

Casa Morada is a 16-suite adults-only boutique hotel on a private island-like setting on the bay side of Islamorada. There is no sandy beach, but the waterfront terrace, infinity-edge pool, and sunset views over Florida Bay are exceptional. This is the best couples retreat in the Keys outside of Little Palm Island.

Islander Resort sits on a wide oceanfront beach at MM 82 with direct ocean access. It offers one of the best value beachfront stays in Islamorada — spacious rooms, a pool, and a relaxed vibe without the premium price tag. Great for families who want beach time and easy access to Islamorada's restaurants and charter docks.

Amara Cay is a modern, well-designed resort on the bay side of Islamorada. The style is more contemporary than the classic Keys look, with a focus on sunset views, a good pool, and the on-site REd restaurant. No sandy beach, but the bay-side location delivers some of the best sunsets in the Keys.

Three Waters Resort & Marina (formerly Postcard Inn) is a modern marina-focused resort at MM 84. The full-service marina with boat slips and fishing charters is the main draw. It is the best base in Islamorada for anglers who want to fish the backcountry and reef without booking a separate marina.

Chesapeake Beach Resort is an oceanfront property with a sandy beach area, private fishing dock, and villa-style accommodations. It combines beach access with easy fishing — cast from the dock or book a charter from nearby marinas. A strong mid-range pick for families who want both beach and fishing.

La Siesta offers oceanfront villa-style suites with full kitchens, three pools, and an on-site fishing pier. The spacious layouts make it ideal for families or groups who want more room than a standard hotel. Directly on the ocean with good snorkeling access.

Pines & Palms is a cottage-style resort on Lower Matecumbe Key with direct oceanfront access and easy reef snorkeling. It has a quieter, more natural feel than the resorts on Upper Matecumbe. Best for travelers who want a laid-back eco-waterfront experience with quick access to the reef.

Ragged Edge is a micro-boutique resort with fewer than 10 units on the oceanfront. It is the most affordable waterfront option in Islamorada — no frills, but you get direct water access, a dock, and genuine Keys character. Best for budget-conscious travelers who care more about location than luxury.

Drop Anchor is a classic Keys marina cottage resort with boat slips and direct backcountry fishing access. It offers the old-school Islamorada fishing lodge experience — nothing fancy, but the marina access and location are strong. Best for anglers who want a home base with boat storage.