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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Upper Matecumbe Key 5 Star Hotels

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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 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.
A tropical resort with a swimming pool, palm trees, and a waterfall.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
United States
Patricia
£184
includes taxes & fees
19 Nov - 20 Nov
Cheeca Lodge & Spa
A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.
A resort with multiple white buildings, each featuring balconies and surrounded by lush greenery and palm trees.
A pool area with clear blue water, white lounge chairs, and palm trees.
A gated entrance to a resort with palm trees and a clear sky.

2. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
United States
Christian
£457
includes taxes & fees
28 Oct - 29 Oct
The Islands of Islamorada
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.
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
£257
29 Oct - 30 Oct
includes taxes & fees
8.8/10 Excellent! (1,188 reviews)
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd Marathon FL
£249
28 Oct - 29 Oct
includes taxes & fees
8.2/10 Very good! (1,008 reviews)
Hawks Cay Resort
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
£187
15 Nov - 16 Nov
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

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

Top Upper Matecumbe Key Hotel Reviews

Find out more about Upper Matecumbe Key

Explore a world of travel with Expedia