Island Bay Resort ★★★

A Bayside Hideaway Between Two Famous Keys

Tavernier is the stretch of the Overseas Highway most drivers pass straight through on their way to somewhere louder: Key Largo behind them, the Islamorada marinas ahead. Island Bay Resort sits on the bay side of that stretch, where the road runs close to the water and the gardens do the work of a wall. Turn in off the highway and the noise stops. What is left is a short run of cottages painted in island colours, a lawn that ends in white sand, and Florida Bay going flat and pale all the way to the horizon. It is a small property, and it behaves like one.

Why It Works

We kept this address because it answers the Upper Keys question: waterfront without a crowd. The resort is adults only, so the beach is quiet at four in the afternoon and at eight in the morning. It faces west onto Florida Bay, which means the sunset happens in front of you rather than an hour down the road. The water gear is included rather than rented by the hour, so a paddle across the shallows costs nothing but the walk to the beach. Ten cottages, one owner-run property, no lobby to cross. That combination is uncommon on this part of the highway.

Why This Location

Tavernier sits midway between Key Largo and Islamorada, which makes it the practical centre of the Upper Keys rather than a compromise between them. John Pennekamp Coral Reef State Park and the Key Largo dive operators are a drive north; the Islamorada charter fleet, its fishing docks and its restaurants are a drive south. Either is a morning. The property faces Florida Bay, the shallow, grassy side of the island chain where the flats fishing and the sunsets are, with the Atlantic reef on the far side of the highway. Key West is roughly two hours further down US-1 and the Miami airports about the same in the other direction.

Fast Facts

• Price: Premium

• Vibe: Barefoot, adults only, gardens and open water

• Rooms: Ten cottages, king one-bedroom and efficiency layouts, kitchenettes and private decks throughout

• Best For: Couples, sunset watchers, paddlers and anglers who want the bay at the door

• Our Favorite Thing About the Hotel: The private white-sand beach on Florida Bay, hammocks and tiki huts set exactly where the light lands at the end of the day

• Dining: No restaurant on site; every cottage has a kitchenette, and the Tavernier seafood counters are minutes up the highway

• Amenities: Complimentary kayaks, paddleboards and snorkelling gear, botanical gardens, bocce court, free parking, boat docking for vessels up to twenty-five feet

• Attractions: John Pennekamp Coral Reef State Park, the Islamorada sportfishing marinas, the Florida Bay flats, Key West about two hours south

The Cottages, and What Comes With Them

Guests stay in freestanding cottages rather than along corridors, decorated in bold Bahamian colour and laid out as king one-bedrooms and efficiencies. Each has a kitchenette, and that changes how a stay works: breakfast on your own deck, a cooler packed before the boat, dinner cooked after a long day on the water instead of a drive back out to the highway. Every cottage has its own outdoor space. The efficiencies suit two people.

On the Water Without Leaving the Property

The bay frontage is the point of the place. Kayaks, paddleboards and snorkelling gear are there for guests, and the water off the beach is shallow and calm enough to use them without a lesson. Anglers can bring a boat: the dock takes vessels up to twenty-five feet, which covers most flats skiffs and bay boats. Between outings the grounds are arranged for doing nothing well, with hammocks slung in the botanical gardens, tiki huts for shade and a bocce court on the lawn. Massage can be arranged on site.

What to Know Before You Book

This is an adults-only property, so it is built for couples rather than for a family trip. Check-in runs from three in the afternoon to six in the evening and check-out is at eleven, worth planning around if you are driving down from Miami. Parking is free and on site, and you will want the car: the Upper Keys are strung along a single highway and everything worth reaching is a drive. Come for the bay side and the quiet, and take the reef, the charter boats and Key West as excursions.