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

Jill Martin | April 25, 2018

Money can’t buy love, according to The Beatles’ famous anthem, but it can buy some pretty amazing experiences. And that is precisely what these luxe resorts in the Florida Keys deliver. We’re talking mind-blowing views, over-the-top amenities, unique locations, and superb accommodations. There’s just one catch--it will cost you.

#9

Little Basin Villas

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

#8

Postcard Inn Beach Resort & Marina at Holiday Isle

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

#7

Ocean Key Resort & Spa

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

#6

Casa Marina, A Waldorf-Astoria Resort

Why it made the list

History meets luxury at this landmark resort that boasts the largest private beach in Key West. Even though it first opened in 1920, rooms and suites are modern and comfy, but the real wow factor is out back; two tropical pools, lots of relaxation space, and expansive ocean views. Spa al Mar even offers beachside massages, and the onsite dining won’t disappoint.

If you’ve got the money, honey, this resort delivers. Histor Read More

#5

Playa Largo Resort & Spa

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

#4

Cheeca Lodge & Spa

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

#3

The Moorings Village

Why it made the list

So much lushness for one property, it just isn’t fair. This 18-acre oceanfront resort is dotted with classic Keys cottages and graceful palms that stretch and bend above windy pathways (one of which leads to their onsite spa). Fans of the Nexflix show Bloodline, know this property as the Rayburn House, but everyone else knows this is the place for tranquility and privacy.

It’s all about privacy and solitude at this stunning oceanfr Read More

#2

Sunset Key Cottages

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

#1

Little Palm Island Resort & Spa

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

  • 9. Little Basin Villas
    84 Johnston Road,Islamorada,Forida,USA,33036
  • 8. Postcard Inn Beach Resort & Marina at Holiday Isle
    MM 84 OS, 84001 Overseas Hwy.,Islamorada,Florida,USA,33036
  • 7. Ocean Key Resort & Spa
    Zero Duval St.,Key West,Florida,USA,33040
  • 6. Casa Marina, A Waldorf-Astoria Resort
    1500 Reynolds St.,Key West,Florida,USA,33040
  • 5. Playa Largo Resort & Spa
    97450 Overseas Highway,Key Largo,Florida,USA,33037
  • 4. Cheeca Lodge & Spa
    MM 82 OS,Islamorada,Florida,USA,33036
  • 3. The Moorings Village
    MM 81.6 OS, 123 Beach Rd.,Islamorada,Florida,USA,33036
  • 2. Sunset Key Cottages
    245 Front St.,Key West,Florida,USA,33040
  • 1. Little Palm Island Resort & Spa
    MM 28.5 OS, 28500 Overseas Hwy.,Little Torch Key,Florida,USA,33042

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