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

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Upper Matecumbe Key 5 Star Hotels

Top Upper Matecumbe Key 5 Star Hotels

Cheeca Lodge & Spa
Private beach, sun-loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1146)
"Been coming to the keys for 29 years, absolutely the best place we have ever stayed. Staff, rooms, food were second to none. "
The price is £174
includes taxes & fees
17 Aug - 18 Aug
Cheeca Lodge & Spa
Condo in the Keys
Outdoor pool

Condo in the Keys

5.0 star property
8.8 out of 10, Excellent, (9)
"Thoroughly enjoyed our stay! The pool, beach area and pickleball courts were fantastic! Also enjoyed the premium cable. "
Condo in the Keys
Waterfront House with Boat Dock
Terrace/patio

Waterfront House with Boat Dock

5.0 star property
6.0 out of 10, (1)
"Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration."
Waterfront House with Boat Dock
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
The price is £211 per night from 7 Sept to 8 Sept
£211
7 Sept - 8 Sept
includes taxes & fees
8/10 Very Good! (1,000 reviews)
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.
PoolSpaHot tubBreakfast includedWaterpark
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
Islamorada showing a beach bar

Top Upper Matecumbe Key Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Golf course could use just a little work. Everything else was great."
Max 3-night trip
Posted 3 days ago
Cheeca Lodge & Spa