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

Compare and book 5 Star hotels in Upper Matecumbe Key, Islamorada

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Check availability on Upper Matecumbe Key 5 Star Hotels

Tonight
2 Sept - 3 Sept
Tomorrow
3 Sept - 4 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for Upper Matecumbe Key 5-star hotels

Balcony
Premium bedding, in-room safe, desk, laptop workspace
Poolside bar
Property grounds

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Mian
£178
includes taxes & fees
7 Sept - 8 Sept
Cheeca Lodge & Spa
Terrace/patio
Staircase
Egyptian cotton sheets, premium bedding, memory-foam beds, desk
Design Villa, Canal View | Dining room

2. Waterfront House with Boat Dock

Waterfront House with Boat Dock
Tavernier
United States
Philip J
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 Upper Matecumbe Key.
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL
£211
13 Sept - 14 Sept
includes taxes & fees
8.2/10 Very good! (1,006 reviews)
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
£238
28 Sept - 29 Sept
includes taxes & fees
8.6/10 Excellent! (1,173 reviews)
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
£164
17 Sept - 18 Sept
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

Venture to sights like Bud n' Mary's Dive Center and Florida Keys Brewing Co. as you discover Upper Matecumbe Key.

See all hotels in Upper Matecumbe Key
A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
Photo by Cameron Abbott

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