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 ￥37,187

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Check availability on Upper Matecumbe Key 5 Star Hotels

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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.
A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.
A spacious lobby with a seating area, a bar, and a large window providing a view of the outdoors.
A tropical resort with a swimming pool, palm trees, and a waterfall.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Morgan
￥29,304
￥44,545 total
includes taxes & fees
Oct 19 - Oct 20
Cheeca Lodge & Spa
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
A gated entrance to a resort with palm trees and a clear sky.
A pool area with clear blue water, white lounge chairs, and palm trees.

2. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
￥76,741
￥96,584 total
includes taxes & fees
Oct 20 - Oct 21
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.
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

97000 Overseas Hwy Key Largo FL
￥46,536
￥61,068 total
Oct 28 - Oct 29
includes taxes & fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL
￥31,883
￥48,021 total
Oct 28 - Oct 29
includes taxes & fees
Hawks Cay Resort
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
￥22,763
￥37,187 total
Oct 20 - Oct 21
includes taxes & fees
Amara Cay Resort
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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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