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

Upper Matecumbe Key 5 Stars Hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Upper Matecumbe Key 5 Star Hotels

Tonight
Sep 1 - Sep 2
Tomorrow
Sep 2 - Sep 3
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

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 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.
A bar area with a thatched roof, wooden chairs, and a view of the ocean.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Mian
₩203,772
₩329,256 total
includes taxes & fees
Sep 7 - Sep 8
Cheeca Lodge & Spa
A balcony with white furniture, a ceiling fan, and a view of a boat and water.
A white staircase leading to a covered outdoor area with a white fence and palm trees.
A two-story building with a balcony, surrounded by a white fence and palm trees.
A kitchen with wooden cabinets, a black countertop, and two bar stools.

2. Waterfront House with Boat Dock

Waterfront House with Boat Dock
Tavernier
United States
Philip J
Waterfront House with Boat Dock
Save an average of 15% on thousands of hotels when you're signed in

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
₩253,676
₩390,527 total
Sep 15 - Sep 16
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
₩324,094
₩440,002 total
Sep 28 - Sep 29
includes taxes & fees
8.6/10 Excellent! (1,179 reviews)
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
₩203,458
₩329,542 total
Sep 3 - Sep 4
includes taxes & fees
Amara Cay Resort
Still don't see what you're looking for?
See all properties in Upper Matecumbe Key.
You can also use these popular filters to refine your search.
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..

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

Top Upper Matecumbe Key Hotel Reviews

Explore a world of travel with Expedia