Caloosa Cove Resort - With Full Kitchens

Where the Charter Boats Leave Before Breakfast

Islamorada calls itself the sportfishing capital of the world and mostly gets away with it. Caloosa Cove sits at the southern end of it, on Lower Matecumbe Key, spread across fifteen acres of oceanfront where the highway finally runs out of shops and the water takes over. The layout is old Keys and none the worse for it: low buildings facing the Atlantic, a heated pool, a strip of sand, a tennis court under the palms, and at the far edge a working marina with a tackle shop attached. By seven in the morning half the property is already on the water.

Why It Works

Because the resort and the marina are the same place. A guest can walk from a suite to a chartered boat in two minutes, buy bait on the way and be back on the dock at midday with something to clean. Every one of the thirty suites is oceanfront with a kitchen and a balcony, which is the correct format for that rhythm, and fifteen acres means nobody queues for a lounger. It is a practical resort rather than a designed one, and for a traveller who is here to fish or to dive, practical wins.

Why This Location

Lower Matecumbe is the quiet end of Islamorada, past the galleries and the restaurant strip, where the island narrows to a ribbon between the Atlantic and the bay. The reef and the wrecks lie offshore, the backcountry flats and Florida Bay open to the west, and the run to either is short from the resort dock. Annes Beach and its shallow sandbars are a couple of minutes up the highway, the Islamorada restaurants and tarpon docks a short drive north, and Marathon and the Seven Mile Bridge lie the other way. Miami and Key West are each about two hours by road.

Fast Facts

• Price: mid to upper range for Islamorada

• Vibe: old Keys, low rise, fishing first, unpretentious

• Rooms: 30 oceanfront suites, all with kitchens and balconies

• Best For: anglers and divers, boat owners, families on a long stay

• Our Favorite Thing About the Hotel: the bait and tackle store on the property, which tells you more about the place than any brochure

• Dining: restaurant on site and a general store for provisions, with the Islamorada seafood houses a short drive north

• Amenities: full service marina with dockage, fishing charters, heated pool, sandy shore, tennis court, barbecue facilities, free parking

• Attractions: the Islamorada sportfishing fleet, Annes Beach, the Florida Reef dive sites, Everglades backcountry

Suites That Face Nothing but Water

The accommodation is arranged so that every unit looks at the Atlantic, which on a narrow key takes some doing. Layouts run from compact studios to one bedroom suites, all with full kitchens and a balcony or terrace, and the larger ones absorb a family without difficulty. Furnishing is comfortable rather than fashionable, the sort of interior that survives wet swimsuits and tackle boxes. What sells them is the balcony at six in the morning, coffee in hand, watching the first boats leave the cove.

The Marina, the Tackle Shop and the Day Ahead

The marina takes visiting boats and books charters, and the general store keeps bait, ice and the small things a fishing morning needs. Offshore boats go for sailfish, mahi and tuna, backcountry guides run for tarpon, bonefish and permit on the flats behind the island, and the dive boats work the reef and the wrecks. For anyone towing a trailer down the highway, this is the rare Keys resort where the boat sleeps as close to the water as you do.

Between the Reef and the Backcountry

What makes this stretch of Islamorada worth a week is the choice of water. Ocean side, the reef line runs parallel to the key, with snorkelling in a few feet of water and diving beyond it. Bay side, the flats and mangrove creeks stretch towards the Everglades, where the fishing is technical and the light at dusk is the reason people photograph this place. The resort sits between the two, which is the argument for booking here rather than in the middle of town.