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 SAR 1,040

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on Upper Matecumbe Key 5 Star Hotels

This weekend
Next weekend

Our top choices for Upper Matecumbe Key 5-star hotels

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,502 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is SAR 680
SAR 1,040 total
includes taxes & fees
29 Nov - 30 Nov
Cheeca Lodge & Spa

2. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (83 reviews)
"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."
United States
Catherine
The price is SAR 2,513
SAR 3,102 total
includes taxes & fees
29 Nov - 30 Nov
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.
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..

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

Top Upper Matecumbe Key Hotel Reviews