Find 5 Star Hotels in Islamorada, FL from ￥49,021

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Check availability on Islamorada 5 Star Hotels

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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 Islamorada 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 ￥40,212
￥56,674 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cheeca Lodge & Spa
Outdoor pool
Condo in the Keys

Condo in the Keys

Condo in the Keys
5.0 star property
Tavernier
8.0 out of 10, Very Good, (13)
"Love the location "
United States
Angela
Condo in the Keys
Design Villa, Canal View | Balcony
Waterfront House with Boat Dock

Waterfront House with Boat Dock

Waterfront House with Boat Dock
5.0 star property
Hammer Point
6.0 out of 10, (1)
"Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration."
United States
Matthew
Waterfront House with Boat Dock
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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 Islamorada.
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
The price is ￥33,436 per night from Jan 6 to Jan 7
￥33,436
￥49,021 total
Jan 6 - Jan 7, 2026
includes taxes & fees
8.8/10 Excellent! (1,266 reviews)
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PoolSpaHot tubBreakfast includedWaterpark
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 Islamorada

The turquoise waters between the Keys offer world-class fishing that even beginners can enjoy with knowledgeable local guides. Spend mornings snorkeling coral reefs teeming with tropical fish, then unwind at waterfront restaurants where chefs cook your fresh catch.

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Islamorada featuring a sunset and general coastal views

Top Islamorada 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

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Islamorada?
There are many different pricing options for 5-star hotels in Islamorada on Expedia. How much you'll pay will depend on when you travel, trip length and other factors. Compare available accommodations for your desired dates and use our pricing and other filters to lock in the ideal high-end stay.

  • Search for the lowest price per night from ￥49,021

What makes a hotel 5 stars in Islamorada?
In Islamorada, a hotel must offer a certain amount of high-end amenities to earn 5 stars. These may include on-site gyms, spas and saunas, gourmet restaurants, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their superior service. You can look forward to things like nightly turn-down services, in-room massages and concierge services. Some may also offer additional touches like welcome gifts.
Are there any 5-star all-inclusive resorts in Islamorada?
Find a luxurious escape that includes your room, meals, activities and entertainment in Islamorada with the help of Expedia's filters. Search for properties with a 5-star rating and select the "All inclusive" filter. Be sure to check what's included in the price. That way, you'll be ready to maximize all the perks on offer as soon as you arrive.