A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Find 5 Star Hotels in Upper Matecumbe Key, FL from ￥39,365

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Check availability on Upper Matecumbe Key 5 Star Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Upper Matecumbe Key 5-star hotels

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,491 reviews)
"Beautiful resort"
United States
Patricia
The price is ￥24,753
￥39,365 total
includes taxes & fees
Nov 1 - Nov 2
Cheeca Lodge & Spa
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

2. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (82 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is ￥82,210
￥102,812 total
includes taxes & fees
Oct 29 - Oct 30
The Islands of Islamorada
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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 Upper Matecumbe Key.
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL
The price is ￥34,315 per night from Nov 15 to Nov 16
￥34,315
￥53,015 total
Nov 15 - Nov 16
includes taxes & fees
8.2/10 Very Good! (1,007 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 Upper Matecumbe Key

Check out the local area in Upper Matecumbe Key—home to attractions like Bud n' Mary's Dive Center and Florida Keys Brewing Co..

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A shark sculpture with a sign above it that reads "Islamorada Florida Keys".

Top Upper Matecumbe Key Hotel Reviews

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