Florida Keys 5 Stars Hotels

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Check availability on Florida Keys 5 Star Hotels

Tonight
Dec 31 - Jan 1
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Jan 1 - Jan 2
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Jan 2 - Jan 4
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Jan 9 - Jan 11

Our top choices for Florida Keys 5-star hotels

Private beach, sun loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1280)
"Fabulous waterfront, activities, and dining as well as the staff. "
Canada
David
The price is ₩430,449
₩589,536 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cheeca Lodge & Spa
Property grounds
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa
5.0 star property
Marathon
9.2 out of 10, Wonderful, (1070)
"Beautiful property, staff are very friendly "
United States
Leann
The price is ₩461,929
₩610,855 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Isla Bella Beach Resort & Spa
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Florida Keys.
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL
The price is ₩331,690 per night from Jan 4 to Jan 5
₩331,690
₩473,752 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8/10 Very Good! (1,003 reviews)
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Florida Keys

Snorkel crystal-clear waters teeming with colorful fish, then feast on fresh-caught lobster at a laid-back waterfront shack. Drive the scenic Overseas Highway, stopping at Key West's Ernest Hemingway Home and Dry Tortugas National Park for island adventures.

See all hotels in Florida Keys
Higgs Beach showing a sandy beach and tropical scenes as well as a large group of people

Top Florida Keys Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"It was over the top amazing"
scot 3-night trip
Posted 4 days ago
Cheeca Lodge & Spa
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

10/10 Excellent
"Beautiful property, staff are very friendly "
Leann 1-night trip
Posted 11 days ago
Isla Bella Beach Resort & Spa

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Florida Keys?
You can find several pricing options for a 5-star hotel in Florida Keys on Expedia. The amount you pay will depend on your travel dates, length of your trip and other factors. Compare all of the available accommodations for your chosen dates and make use of our pricing and other filters to score the ideal upscale stay.

  • Search for the lowest price per night from ₩473,752

What makes a hotel 5 stars in Florida Keys?
From gourmet restaurants and 24-hour gyms to pools and deluxe bedding, the 5-star experience in Florida Keys is all about comfort and indulgence. But it calls for more than just top-notch perks to earn a 5-star rating. Stays must also provide outstanding guest-focused services like in-room massage treatments, on-site laundry and dry cleaning and 24/7 room service.
Are there any 5-star all-inclusive resorts in Florida Keys?
Find an indulgent escape that includes your lodging, meals, drinks and entertainment in Florida Keys with Expedia's filters. Search for hotels rated 5 stars and click on the "All inclusive" filter. Double-check what's included in the upfront price. This way, you'll be ready to maximize all the premium perks from the moment you arrive.