Florida Keys resorts for unwinding in style

With crystal-clear, turquoise water, colorful coral reefs, and broad stretches of white-sand beach, the Florida Keys are the closest thing to the Caribbean. Literally, and figuratively. Nearly 400 islands stretch 150 miles south of Miami on the Overseas Highway. It’s a one-of-a-kind drive everyone should do at least once.

The scenery isn’t all the Keys share with their neighbors to the south. The attitude here is definitely laid-back, and everything gets done on “island time.”

Key West gets most of the attention, and you should absolutely visit the “Conch Republic” while you’re in the keys. But some of the best Florida Keys resorts are in the upper or middle Keys.

Upper Florida Keys resorts.

We don’t usually recommend places that can be described as “a dive,” but Jules’ Undersea Lodge is an exception. Guests here spend the night 30 feet beneath the surface in a former research lab. There are two rooms — which share a living area and bath – each with large windows for watching the underwater panorama. You’ll have to put on scuba gear to get here, but once you’re ensconced, your meals will be delivered via room service.

Arguably the hippest resort in the Florida Keys, Casa Morada was built in the 1950s and redone by former members of hotelier Ian Schrager’s team. Today, it’s a stylish boutique hotel with 16 suites, a Zen garden, and a grotto pool. The suites have cool, terrazzo floors and either a patio or a private garden. Some have al fresco showers or Jacuzzis. Free use of bikes and kayaks is a nice plus. You can enjoy breakfast – which is included in the rate – on the beach-front terrace.

Golfers should make a bee line for Cheeca Lodge, in the Upper Keys. The 27-acre grounds are beautifully landscaped and there’s a nine-hole golf course with pretty views. Rooms are large and well equipped. But with golf, tennis, water sports, and a full-service spa, no one spends much time there. For the most enjoyable experience, upgrade to a room with an ocean-view balcony. Their children’s program makes this a good choice for families. With two restaurants and two bars, you need never leave.

If you’ve always wanted to swim with dolphins, you can do it in the saltwater lagoon at Hawk’s Cay – if you make arrangements well in advance. If that’s not appealing, there’s also sailing, water skiing, snorkeling, fishing, and tennis. With nearly 500 rooms, it’s the largest Florida Keys hotel. If you’re traveling with friends or family, book one of the two- or three-bedroom villas. These have kitchens and washer/dryers. Hawk’s Cay has five pools, including one for adults, five restaurants, and a 7,000-square-foot spa.

One of the most sophisticated Florida Keys hotels, The Moorings has 18 luxurious one-, two-, and three-bedroom cottages on the best beach around. Decorated in the island style with nice verandas, the cottages have full kitchens and most have washers and dryers. Set on 18 acres, the complex is extremely private, and the beach is huge. There’s a large pool, tennis, a spa, and non-motorized water sports.

Middle Florida Keys resorts.

As the name suggests, Tranquility Bay is a great place to relax and unwind. The two-and three-bedroom suites here all have views of the Gulf of Mexico from the proch. There’s a beachfront bar, excellent restaurant, fitness center, spa, and big heated pool.

Three miles off the coast of Little Torch Key, Little Palm Island is a five-acre sanctuary for the rich and famous. Guests – who arrive by boat or seaplane – are accommodated in beach-front bungalows that have slate indoor/outdoor showers, thatched roofs, and private porches. The Grand Suites have outdoor hot tubs and two bathrooms. To keep things serene, rooms are without TVs, phones, or alarm clocks, and cell phones are banned in public areas.


Watersports equipment is included in the rate, and there’s a top-notch spa. The restaurant is so good that most guests opt for three meals a day.

One of the most affordable Florida Keys resorts, Parmer’s Resort offers recently renovated, waterfront cottages overlooking Pine Channel. The five-acre property has a heated pool, lots of water sports, and very friendly staff. Many of the cottages have decks or balconies, and some have kitchenettes. And Key West restaurants and shopping are just a half an hour away.

Key West resorts.

Those who want to get away from it all — but still be close to the action — will enjoy Sunset Key, a 27-acre private island that’s a ten-minute boat ride from The Westin Key West Resort & Marina. Accommodation range from one- to four-bedroom cottages, and guests have privileges at the sister property.

Find South Beach Miami hotels to visit before or after the Keys.

1) Jules Undersea Lodge
2) Casa Morada
3) Cheeca Lodge
4) The Moorings
5) Tranquility Bay
6) Little Palm Island Resort
7) Parmer’s Resort
8) Sunset Key Resort

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