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Hook & Barrel
A Lifestyle Magazine for Modern Outdoorsmen

Deep sea fishing doesn’t get much better in America than it does in the Florida Keys, and about halfway between Miami and Key West you’ll find the Florida Keys’ best place for sport fishing in Islamorada. Whether you’re towing your own boat down the Overseas Highway or hopping on a charter once you get there, you’ll find the aquamarine waters off this tranquil chain of islands teeming with grouper, mahi, wahoo, and marlin. Restaurants in town will happily cook up your catch for you too, making it the ultimate anglers’ vacation. Here is our round-up of the best hotels for an Islamorada fishing trip.

With fishing this good, a multi-day trip is a must, which then raises the question of where to stay. Islamorada is full of hotels that offer dock slips and charters right out your front door, many with restaurants who’ll prepare your day’s catch for you too. Where you go depends on a lot of things, like whether you’re there with family, or if you plan to fish all day or spend more time by the pool. Whatever you’re doing, here’s a look at the best resorts to call home during an Islamorada fishing adventure.

Postcard Inn

Best Hotels For An Islamorada Fishing Trip

84001 Overseas Highway

The storied Postcard Inn is the flagship property for the Islamorada Resort Collection, which also includes Amara Cay, La Siesta, and Pelican Cove. Guests can use the amenities at all four, charging stuff back to their rooms no matter where they stay. The largest and most famous is the Postcard Inn, formerly known as Holiday Isle. It made its name as the birthplace of the Rum Runner, a lesson you’ll learn at the dollar bill-filled Tiki Bar which still sits right on the bay. More important than the bar’s history is its location, just a few steps from the resort’s private marina. This makes it literally impossible to walk from your boat to your room without stopping for a drink.

Before you hit the open seas, stop into Abel’s Tackle and Goods, the best-smelling bait shop on the planet. It’s been on property since 1961, though it recently relocated to a spot right on the marina. It offers pretty much everything you’ll need for an afternoon chasing mahi and marlin, from bait to snacks and sunscreen. From there, step out the back door to any number of fishing charters you can book onsite. If you brought your own boat, Postcard Inn offers packages that include dock space too.

Cheeca Lodge

Best Hotels For An Islamorada Fishing Trip

81801 Overseas Highway

The Keys are often called America’s Caribbean, and if you want that feeling of tropical island isolation book a room at Cheeca Lodge. The hotel sits on 27 lush acres, completely removed from the traffic of the Overseas Highway and set right on the water. The poolside tiki bar goes a long way towards making your nights off the boat feel like a tropical vacation, as do the massive lagoon pools where you can kick back with a beer and look out over the sea.

The place is so relaxing you might forget to go fishing. So if you do miss the boat, borrow the lodge’s gear and walk to the end of its 500-foot pier to try your luck. If you’ve brought your family along Cheeca Lodge has plenty for them to do too, from kayaking to Scuba diving.  And if you feel like taking a day off the water yourself, there’s a nine-hole executive golf course designed by Jack Nicklaus. The onsite restaurants will cook your catch, though if the bite wasn’t on you won’t go wrong with sushi at Nikai or pizzas at Mia Cucnia. Once you’re done, you can retire back to breezy rooms done up in palm fans and tropical décor for a little luxury after your day on the water.

Amara Cay

Best Hotels For An Islamorada Fishing Trip

80001 Overseas Highway

Imagine waking up before the ass crack of dawn, grabbing your rod, walking out the sliding patio door of your hotel room and right onto a deep sea fishing charter. That’s entirely possible if you book one of the beachside cabanas at Amara Cay, which sit about 50 yards across the beach from the hotel’s private dock. It’s about as convenient as fishing gets in Islamorada, and if you’ve got your own boat you can dock it there too, for a fee.

For anglers, this is obviously Amara Cay’s biggest selling point. But the hotel is more than just an easy place to wake up and fish. It’s got an elevated private beach, meaning you can stretch out on the sand and never worry about seaweed washing up next to you. It’s also got a lively tiki bar right next to the pool, boasting some of the better bar food in the middle keys (though the downstairs restaurant ReelCatch will cook whatever you hauled in that day too). The rooms are bright and airy, and though there’s not much particularly remarkable about them they all offer private balconies for enjoying a post-fishing cigar.

Fisher Inn Resort and Marina

Best Hotels For An Islamorada Fishing Trip

84951 Overseas Highway

If you came to the Keys to fish more than lay by the pool, but you still don’t want to drive to a marina every day, Fisher Inn is the move. While it’s not quite as plush as some other Islamorada resorts, the Fisher Inn is still clean and comfortable with larger-than-average rooms boasting kitchenettes and free breakfast. The resort’s biggest selling point is its private marina, where boat slips only cost $40 per day for hotel guests – less than parking at most downtown city hotels.

There’s no restaurant onsite but nothing in the Keys is ever that far. You can also book charters that leave directly from the marina, then relax by the small but rarely-crowded pool once you’re finished. Rooms range from double queens all the way up to villas, too, so if you and your crew all want to pile into one room you can still do it comfortably.

Pelican Cove

Best Hotels For An Islamorada Fishing Trip

84001 Overseas Highway

Sometimes you want to fish, then go back and party. Sometimes you want to fish, then retreat to  total serenity to recharge for the next day. For that second group, might we suggest Pelican Cove, Postcard Inn’s adult-oriented neighbor that’s a quiet escape from the busy resort next door. This former condo building offers all King rooms, so you can spread out and pass out after a day of casting lines and drinking cold beers. The hotel doesn’t promote to families and doesn’t allow pets, so if you’re rolling solo it’s just about paradise.

That doesn’t mean Pelican Cove has nothing to do other than sleep. Like most of the Islamorada Resorts collection it has an elevated private beach with lounge chairs. There’s also a small poolside bar, and a makeshift driving range where you can hit golf balls made of fish food into the turquoise water beyond. If you’re up for some island exploration, jump on a 90-minute jetski tour from the small floating dock near the parking lot. Getting to the fishing boats isn’t too hard either, as you’re barely five minutes on foot from the marina at Postcard Inn.

La Siesta

Best Hotels For An Islamorada Fishing Trip

80241 Overseas Highway

Going fishing with a few buddies is always a great escape. But sometimes fishing trips are family affairs, where huge groups of spouses, kids, and other relatives come along even if they’re never setting foot on a fishing boat. For those occasions, look to La Siesta, where large, two-room suites with small kitchens are the norm. Though if you’ve got a bigger group, you can also rent one of La Siesta’s massive beach houses, which come with a dock slip included. If you bring a boat and stay in a regular room, you can easily park it at La Siesta’s lot too, barely 30 yards from the boat ramp.

Of course, since it is a family resort that means there will be a lot of kids splashing around the pool or playing on the resort’s private beach. There’s not much in the way of food, and the drinks at the onsite pool bar are limited. But if you came here for some quality time on the water with your family, it’s the best of the bunch. Especially when staying at La Siesta means you can hit three other resorts during your stay.

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