Where to Stay in The Keys When Money Doesn’t Matter

Why it made the list

From your second-story, expansive bedroom in villa 9, step onto your private veranda and take in the views of Little Basin waterway and the Florida Bay. Glorious, especially at sunset. Each of the nine conch-style villas is 3-bedroom/3.5 bath, with a gourmet kitchen, and they’re right in the heart of Islamorada. With no real signage on US1, they’re quite the find (you can thank me later).

If you’ve ever wanted to quit your job and move to the Keys, Read More

Why it made the list

If you’ve ever dreamed of living on the ocean in the Florida Keys, now’s your chance. Stay in your own one- to three-bedroom home, each one an upscale Caribbean-inspired fantasy, especially the "Royal Palm." Seriously, you may go weak in the knees when you step inside, ogle the Venetian glass marlin, then open the floor-to-ceiling glass sliders that lead to your ridiculously oversized terrace, and panoramic view of the Atlantic. Dreams do come true.

When you imagine the Florida Keys, this is the place that co Read More

Why it made the list

Ocean Key is the yin and yang of a Key West getaway, it’s relaxing and exhilarating at the same time. And talk about location. The action happens just outside--you can even gawk at the soiree from your balcony if you opt for that view. While many resorts tone down tropical vibrancy, Ocean Key embraces it. Airy and bright suites; a sea of turquoise loungers and pillows poolside; and a pier of electric green umbrellas. Too much? Head to their spa and wind down in grand style.

Luxury can be fun, especially when it’s at the edge of every Read More

Why it made the list

As the new kid on the block, this bayside resort is making quite the splash among affluent travelers. Why, you ask? They’ve got the largest spa in the Keys, a picturesque pool and deck, sumptuous dining options, and for those seeking enhanced privacy, a resort within a resort offering private bungalows or your own two-story, colonial beach house.

This is a destination resort in every sense. Multiple restau Read More

Why it made the list

This is one of the largest resorts on the list, but it also boasts more amenities and activities. Mix and mingle as you enjoy three splendid restaurants, two pools, a 9-hole golf course, a pampering spa, and a bevy of watersports. Or, just chill in a lavish oceanfront suite, complete with a Japanese soaking tub that fills from the ceiling.

See and be seen at Cheeca Lodge and Spa. Read More

Why it made the list

White picket fences. Pastel-colored clapboard cottages. Impeccable service. Island life is good, and it’s only a seven-minute boat ride from Key West. One- to four-bedroom cottages offer space galore, especially the four-bedroom, with a chef’s kitchen and your own plunge pool. Waterfront dining on the sand in an award-winning restaurant and a heavenly spa complete the fantasy. Your time and your money are well spent here.

Looking for a quiet, island getaway that will afford you pam Read More

Why it made the list

Considering you can only get here by boat or seaplane, and there are just 30 suites housed in 15 thatched-roof bungalows, the exclusivity factor of this insanely romantic resort is unmatched. No cell phones, TVs, or distractions--and no one under the age of 16. You will find your happy place on this very private island, and you might be barefoot in the sand drinking a signature Gumby Slumber when you do. And what better way to find your happy place than that?

There's a long list of notable guests that have chosen to sp Read More