The Islands of Islamorada

The Slow Road on the Ocean Side of Matecumbe

Islamorada has two roads. The Overseas Highway carries the traffic and the bait shops; Old Highway runs beside it on the ocean side, narrow and residential, with driveways that end at the water. The Islands of Islamorada is one of those driveways. Behind the gate the property opens onto a private beach, low white villas set along the shoreline, pools looking at nothing but Atlantic, and a shoreline shallow enough to wade out from. Thirty one units in total, which on a stretch of coast measured in hundreds of rooms is close to having the beach to yourself.

Why It Works

The format is the reason. Villas and suites rather than corridors of rooms means a family or a group of friends can take a building, close the door and still be twenty steps from the sand. The resort keeps its own boats, so the reef, the flats and the low tide sandbars are reachable without booking through a third party, and the service runs on concierge lines rather than desk lines. It is the luxury end of Islamorada without the scale of the big beach resorts, and it sells the one thing they cannot: quiet.

Why This Location

Upper Matecumbe is the centre of Islamorada, and the ocean side of Old Highway is its best address. Everything is a short drive: Founders Park with its beach and pool, the History of Diving Museum, Theater of the Sea up at Windley Key, the fish houses where the charter catch is cooked, the galleries on the highway. The reef sits a few miles offshore and the backcountry flats begin on the bay side, both within twenty minutes of the dock. Key Largo is half an hour north, Marathon the same to the south, and Miami about ninety minutes away.

Fast Facts

• Price: luxury tier for Islamorada

• Vibe: private, white on blue, discreet, resort at villa scale

• Rooms: 31 waterfront villas and suites

• Best For: couples, multigenerational groups taking a villa, wedding parties

• Our Favorite Thing About the Hotel: the boat run to the sandbars, which puts you standing in waist deep water a mile from land

• Amenities: private beach, oceanfront pools, hot tub, marina and private charters, paddleboarding, fishing, spa and massage, fitness room, free private parking

• Attractions: Founders Park, History of Diving Museum, Theater of the Sea, the Florida Reef and the Islamorada sandbars

Villas and Suites at the Water Line

Accommodation runs from suites to full villas, all of them waterfront, and the difference matters more here than the decor. A suite gives a couple a terrace and a view; a villa gives a group its own front door, its own outdoor space and the ability to eat together without a reservation. The style is bright and coastal, white walls and pale timber against the blue outside, which is the right restraint on a plot where the ocean is doing the decorating. Ask for the units closest to the beach: the walk matters at this size.

Sandbars, Reefs and the Boat That Takes You There

The best hours in Islamorada happen on the water, and this property is set up for it. Private charters run out to the coral heads for snorkelling and diving, and to the sandbars that rise out of the shallows at low tide, where boats raft up and the water is knee deep for a hundred metres. Paddleboards go out from the beach for the calm early mornings, and the flats behind the island hold the tarpon and bonefish that made the reputation of this stretch of the Keys.

A Beach That Fills With Weddings

The private shoreline and the small number of units make this an easy property to take over, and it is booked accordingly for weddings and family gatherings, with the ceremony on the sand and the reception under the palms. For anyone travelling in high season it is worth asking what else is on the calendar, and for anyone planning a celebration it is worth asking how much of the resort can be held. Either way, the answer shapes the week.