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 ￥44,133

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Check availability on Upper Matecumbe Key 5 Star Hotels

Tonight
Oct 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
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 view of the sea, and a pier with boats.
A bar area with a thatched roof, wooden chairs, 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 hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Patricia
￥29,032
￥44,133 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.
A pool area with clear blue water, white lounge chairs, and palm trees.
A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.
A beachfront hotel with multiple-story buildings, a pool, and palm trees.

2. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
￥76,155
￥95,845 total
includes taxes & fees
Oct 28 - Oct 29
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
￥34,180
￥52,806 total
Nov 15 - Nov 16
includes taxes & fees
Hawks Cay Resort
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
￥38,461
￥51,917 total
Nov 9 - Nov 10
includes taxes & fees
8.8/10 Excellent! (1,193 reviews)
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Islander Resort

Islander Resort

82100 Overseas Highway Islamorada FL
￥29,366
￥44,507 total
Nov 15 - Nov 16
includes taxes & fees
9.4/10 Exceptional! (1,153 reviews)
Islander 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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