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5 Ideal Hotels for a Laidback Florida Keys Vacation

When you’re in search of charm, history, and plenty of rest and relaxation away from crowds, these places will do the trick.
Casa Marina
Even at over 100 years old, Casa Marina, A Waldorf Astoria Resort, is the epitome of old Key West beauty and casual luxury. Casa Marina, A Waldorf Astoria Resort

When you’re itching to get away but are focused on finding destinations where there are no crowds, you sometimes have to fly halfway around the world for satisfaction. The problem is, however, that you might not have the extra travel time to spare, when you only have a few vacation days remaining.

While some people might think the Florida Keys is all about action, it’s also one of the best choices for a simple, low-key escape. The region offers that tropical vibe and gin-clear water, all reachable by car—or domestic flight—and these specific hotels and resorts are always offering peace, quiet, and a whole lot of undeniable Keys charm.

Casa Marina, A Waldorf Astoria Resort

Six-and-a-half beachfront acres on the south side of Key West are reason enough to choose Casa Marina, A Waldorf Astoria Resort for your next getaway. The resort is in the heart of the island, just a mile from the Hemingway House and the Green Parrot Bar. To reach either, you can ride a rented bike from Key West Bicycles, which drops off to the hotel so you get around without being in contact with Uber drivers.

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On property, four categories of ocean-view rooms offer the most fresh air, with balconies or walk-out lanais. The hotel is asking that social distancing be practiced at the pool, as well as the rest of the property.

Perhaps the biggest reason to choose this resort is the white sand beach stretching along the front of the property. Onsite, you’ll also find the watersports concessioner Barefoot Billy’s, offering Jet Ski tours around the entire island, as well as sunset cruises. We love that you can also rent a scooter to explore as much of the island as you like—on your own time and away from everyone else.

Little Palm Island Resort

Little Palm Island Resort
This is exactly what we have in mind when it comes to spreading out. Little Palm Island Resort

For starters, this upscale enclave sits on its own private island, set apart from Little Torch Key by a 15-minute boat ride—it’s the very definition of getting away. On site, we love the stand-alone bungalows offering a total of 30 suites, all opening to indoor-outdoor living, welcoming in fresh sea breezes.

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The full dining menu is offered in the open-air main restaurant, and in-room dining is a choice for a more private affair. The menu impresses whether you’re choosing a la carte items, such as grouper ceviche, grilled Spanish octopus or foie gras crème brulee, or truly wows if you opt in for the five- and eight-course meals with wine pairings.

As beautiful as the dining area is, guests can also opt to stay in room for a meal, followed by a soak in the outdoor copper tub (available in the island romance suites, island grand, and island premier category suites). And we’d always say yes to the island wellness massage, which includes a CBD treatment to help wash away the anxieties of a stressful year.

Kona Kai

Just 13 cottage-style suites make up the Kona Kai Resort, Gallery and Botanic Garden on Key Largo, creating a quiet and very private atmosphere. Each room has its own unique styling, from the white faux-coral chandeliers of the Banana Suite to the headboard made of oars in the Guava Room suite. Surrounding each room is an abundance of greenery, from clusters of palm trees to hibiscus shrubs—all adding to the feeling of a tropical escape that so lush, it’s easy to forget you’re just 90 minutes from the Miami airport.

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On property, the resort only allows guests 14 years and older, further adding to the serenity. We like that the resort centers on an outdoor experience, including a beach with ping-pong, hammocks, and ample chaise lounges. You’ll find it on the Florida Bay side of Key Largo, with calmer waters that you can explore with the resort’s kayaks, paddle boats and paddle boards. Best of all, there is WiFi free of charge, so if you can make it a working holiday if need be.

Hawks Cay Resort

Hawks Cay Resort
Whether lounging or paddle boarding, guests will thoroughly enjoy the lagoon at Hawks Cay Resort. Hawks Cay Resort

We love that you can spend your whole day outside at Hawks Cay Resort, a 177-room escape on Duck Key, a 2-hour drive from the Miami airport. The resort doesn’t have a beach, but it has its own marina, offering an array of watersports, including fishing charters, paddle boarding, snorkel tours, and private excursions where you can be the only ones onboard.

With five outdoor pools, you can spread out when catching sun. Note that there is an adults-only pool for those who prefer more quiet to read and recharge. For kids, the pirate ship pool packs raining palm trees, water cannons, and shallow areas to keep the little ones entertained.

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Onsite, you’ll also find five restaurants. Angler and Ale, with tons of outdoor seating, dishes up Keys’ seafood classics, including conch fritters to fish sandwiches with the local catch, blackened. The resort also offers boxed lunches and takeaway options, so you can get as private as you like come mealtime.

Bakers Cay Resort

We love the modern, minimalist vibe of this 200-room resort located on the Florida Bay side of Key Largo. The resort offers four categories of room, all with private outdoor balconies as well as indoor seating areas. As much as you’ll love retiring to the privacy of the rooms, the real treat might be the waterfront, as Bakers Cay is one of only a few Key Largo properties with an actual sandy beach.

On the grounds, we especially love the hanging chairs in the Dry Rocks restaurant, where bartenders expertly mix cocktails such as the Some Like It Hot—with pineapple and lemon juice, as well as cinnamon syrup, jalapeno and angostura bitters—that will appeal to a more discerning palette. Of course, you’ll want to stay for sunset, and the fare, from ceviche and smoked fish dip to cilantro lime shrimp tacos.

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