La Siesta Resort & Villas
We selected this resort for something Islamorada mostly lacks: a walk-in beach you can enter...
Most of Islamorada assumes you will charter. Fisher Inn assumes you might tow. It is the only hotel in the village with its own boat ramp, trailer parking and slips, which turns the whole logic of a stay upside down: instead of meeting a captain at dawn somewhere down the highway, you walk out of the room, step onto your own deck and are on the water before the first restaurant opens. The property sits oceanside at 84951 Overseas Highway, around mile marker 85, low and unshowy behind the palms, with thirty-seven rooms and villas arranged around a heated pool and a strip of private beach.
Two reasons carried the decision. The first is that boat ramp, a genuinely rare piece of infrastructure on an island where dockage is the scarcest commodity there is, and the thing that makes this address useful rather than merely pleasant. The second is how the rooms are built around it: kitchenettes, so the cooler gets packed the night before, and a pet policy that means the dog comes too. Islamorada has grander properties. It has very few where the day can start on your own schedule.
Mile marker 85 puts you in the middle of Islamorada rather than at either end, which matters more here than the postcard. Theater of the Sea is less than a mile up the road, close enough to walk if the heat allows. Robbie’s and its tarpon dock, the sandbar boats and the backcountry flats guides are all a short drive south, and Long Key State Park sits beyond that. Northbound, John Pennekamp Coral Reef State Park and the reef dives off Key Largo are within an easy morning. The ocean side means sunrise from the beach and the reef straight out front. The bayside sunset bars are a five-minute hop across the highway.
Price: €€
Vibe: Low-key, nautical, working-day-on-the-water
Rooms: Thirty-seven rooms and villas, most with kitchenettes; the Seaside Villas are the newest category
Best For: Anglers bringing their own boat, divers and snorkellers, travellers with dogs
Our Favorite Thing About the Hotel: The boat ramp and trailer parking, the only set in Islamorada attached to a hotel
Dining: Daily continental breakfast on site; the village’s fish houses and dock bars are minutes away in both directions
Amenities: Private marina with slips, boat ramp and trailer parking, heated oceanview pool, private beach with fire pit and Adirondack chairs, on-site fishing charter, pets welcome
Attractions: Theater of the Sea (under a mile), Robbie’s Marina, the Islamorada sandbar, Long Key State Park, John Pennekamp Coral Reef State Park up in Key Largo
The room stock is practical rather than decorative, and that is the point. Kitchenettes with refrigerators handle the bait, the catch and the six o’clock coffee. The Seaside Villas are the newest rooms on the property, done in a Keys palette and worth the step up if you are staying more than a couple of nights or travelling as two couples. Ask for something facing the water rather than the highway when you book: the difference is the whole atmosphere of the stay, and the categories do not always make it obvious.
The marina is the reason to choose this place and deserves the detail. Slips book separately from the room and go quickly in season, so they are worth securing at the same time as the reservation. The ramp and the dedicated trailer parking spare you the public ramp queue, which in Islamorada on a Saturday is its own small ordeal. If you did not bring a boat, there is a charter operating from the property, which shortens the morning to a walk across the car park. Backcountry, reef and offshore are all within reach of the same dock.
Check-in runs from late afternoon into the evening and check-out is early, which suits a fishing schedule and less so a lazy last morning. Dogs are welcome under the property’s pet programme, worth confirming at reservation along with the slip. The pool is heated, which matters more in the Keys winter than visitors expect. And treat the location as a base rather than a destination: the pleasure of this address is what you leave it for, most of it floating.
We selected this resort for something Islamorada mostly lacks: a walk-in beach you can enter...
We loved how much of the water comes included. Amara Cay is an oceanfront resort...
What we like about this one is how little of the highway reaches it. The...